Dear Santa: My Knees Hurt

{Stay tuned to the end for a giveaway!}

I buy cheap shoes.  I always have.  In fact, I’ve always been a little smug about people who shell out big bucks for shoes, because I couldn’t imagine it was really worth it.

It’s easy to have ideals when your knee joints are, you know, 22 years old. 

But then your knee (and hip and ankle) joints start the downhill slide toward 40.  Suddenly climbing the stairs generates more popping than Orville Redenbacher, and you start to wonder if those quality-shoe people were on to something to begin with. 

Let’s just say I’m reconsidering my smug cheap-shoe buying. 

My husband has some KEEN shoes (these, in fact), and he swears they are all kinds of crazy comfortable.  My noisy knees and I suddenly have our sights set on these:


They’re clogs.  And Mary Janes.  Two of my favorite features in a shoe.  They also have a "metatomical footbed for personalized comfort".  I have no idea what that means.  But I think my knees would like it.

Just in time for Christmas, the KEEN people have offered to give one lucky reader any pair of shoes from their website, absolutely free.  Your pick.  For real.

To enter to win, all you have to do is visit their site, browse around the KEEN site, come back here, and leave a comment saying which pair you think you’d pick.

Oh, and it’s not a requirement, but if you want to, tell me your shoe-shopping philosophy.  Are super-frugal, or do you think that’s one item worth paying up for?

I’ll close down the comments on Tuesday morning, 12/16, and I’ll draw a random winner then.  You must have a valid U.S. mailing address to win. 

Good luck!

*The comments are now closed.*

1,057 thoughts on “Dear Santa: My Knees Hurt

  1. Emily says:

    I would love to win this! Living in New York City is thrashing all my shoes and giving me all sorts of foot pains! I need some decent shoes. I’d pick the Winthrop boots, or the Charleston mary janes, I think!

  2. Stephanie says:

    This choice is tough! I’d probably pick the Wear Around MJs or Barcelona MJs. Both fit my style AND ease of slipping them on without have to tie one more set of laces!
    …That is – if I actually ever paid anything above $15 for a pair of shoes. 🙂

  3. Christina says:

    Oh I used to have that SAME philosophy until I met Dansko Professional clogs. They are my best friends with my feet. seriously.
    But these KEEN shoes look lovely! Off to browse their website! thanks for keeping us in the know!

  4. Tracy says:

    I wish I could call myself frugal, but when it comes to shoe shopping, I’m just plain cheap!
    I love the Trailhead San Sebastion shoes in blue.

  5. Sally says:

    Would love to win this! I’d love the Wear Around MJ because they’re super-cute and I think I could get away with wearing them to work…yay for comfort & style. 🙂

  6. Christa Bartlett says:

    I pay for shoes. I have back issues, and since I am pregnant with my fifth kid, and the ones I have daily with me are 6.5, 2.5, and 1.5 – well, we’ll just say people have a lot of things to call me crazy for besides my expensive shoes.
    I love my plum-colored KEEN mystics. I love my Born bowling-shoes shoes. And I’m rather fond of my ugly Crocs as houseshoes (not street shoes). And I have a pair of Born Mary Jane clogs that tickle my fancy. And my Nikes certainly aren’t lonely. None of them are new – they are all old friends, since a pair of shoes that you actually pay for lasts for years and still looks good. My Mary Jane clogs are five years old and still cute and classic – so for a little polish and some elbow grease, I’ve gotten to enjoy them for about $18 per year. They have at least three more years in them, so my final cost will be about $10 per year. That’s a whole lot better than spending $10 on cheap shoes every year and having my lower back on fire.
    I’d get either the sagey Wasatch Crest, which would replace the Nike’s or just look cute with jeans – or the Orion blue Calistoga Mary Janes, which would look great with most of my favorite summer skirts. The only thing that is stopping me from throwing them in the hypothetic cart and checking out is the price tag. The downside to paying big bucks for shoes is that they must always be a planned purchase.

  7. Christina says:

    Oh geesh, in my excitement, I forgot to mention my heart’s desire… the Wear around Mary Janes look super cute and comfy! Comfort is number one in my book!

  8. Andi says:

    This is a great giveaway! I love the black Winthrop Boots. But, if pressed, I could also be talked into getting my husband a pair of Austins- he has a pair that he loves & have a lot of wear on them.
    I got sold on more expensive shoes during my first pregnancy 4 years ago while living in New York City. I bought a pair of Born sandals & was sold on paying more for my shoes. I love Danskos & think they’re well worth the money- especially their sandals. But, I don’t buy a lot of shoes, so I don’t mind spending more.

  9. Angela says:

    I think the Winterport shoe would be my pick as I walk all winter with my dog. The Winterport would be waterproof and warm. I already have a pair of tall waterproof boots so these would be perfect:)

  10. Elizabeth says:

    I love the Winthrop clog. They look so comfy! And practical. Two of my favorite qualities in a shoe.
    And my shoe philosophy is to buy better quality and spend more if you have to. No payless for me!

  11. lisa mickey says:

    This is so neat.. what a great idea.
    Being frugal and living on one income , I could never justify spending this much on shoes 🙂 !
    But you asked me to dream..
    so I would pick the Winthrop boot.. in cordovan.. 🙂
    Thanks again for linking to the site.. who knows.. maybe some day ..
    Merry Christ-mas..

  12. Erica M says:

    Oh, I know it would be worth it, considering my knee, back, and ankle problems, but I still can’t seem to make myself pay for quality shoes. I’m just way too cheap!
    I’ve picked the CALISTOGA in Black!!

  13. Jenni (One Thing) says:

    I love the calistoga shoe, but also the Winthrop boot! Oh my they are all so cute, and they DO look comfortable.
    I am a terrible, terrible miser when it comes to shoes. My feet are so ugly I don’t think they deserve nice shoes, poor things.
    Thanks for the chance to win, Shannon!

  14. Karen F. says:

    I’m all about the mary jane’s . . . to die for!
    And I’m a cheapo all the way. Maybe if I had money to splurge it would be on a pair of shoes . . . but since I don’t have any moola . . . who knows?!

  15. Anna says:

    I like the Calistoga shoes… I adore my Prada Mary Janes, but they’re getting a little beat up after 5 years and I’m their 2nd owner.
    I find that the more expensive shoes last much longer and smell less (if at all) but can’t justify shelling out the big bucks for them. If I can snag them on clearance, then I’ll do it.

  16. Ashley @ says:

    I like the one you have pictured, but I also love the Portola in Shitake. Plus I just like saying that 🙂
    I am in between. I don’t shop at Payless anymore because my feet hurt when I do, but I can’t spend an arm and a leg because I would like to keep my SAHM status and I would like to keep my hubby!

  17. Christy says:

    The Charleston Mary Jane…too cute!
    I LOVE shoes so I have a tendency to find many that I like! My philosophy is one can never have too many pairs!

  18. Christi says:

    Ooohhh! I would LOVE the Winthrop boots. They are awesome! I don’t know how practical they would be in Texas, but who loves practical anyway?!

  19. Karen says:

    I hate to be a copycat, but I like the Berkleys, too. I also like the Sienna Ballet flats. I like to wear skitrs, so I’d choose some that would look good with them.
    I used to buy cheap shoes, but since being diagnosed with Rheumatoid Arthritis, I have been spending more on shoes that have good support in them. But sometimes I miss my Target shoes!!

  20. life with the wisners says:

    seriously. i mean, keen must have gotten hold of you and your pals. these giveaways for my FAVORITE shoes has me grinning from ear to ear.
    my kid SO needs a new pair of targhees.
    and my philosophy? these shoes rock. i shell out the big bucks for several pairs. and that’s it.

  21. Tami@ourhouse says:

    Fun! Barcelone MJ, or Sierra. I go both ways with the shoes. Cheap for trendy shoes and church shoes, better quality for my everyday shoes. i like Born and when I was pregant, Crocs saved my life.

  22. Becky Bost says:

    After dragging numerous boxes of Christmas items down from the attic and downstairs to the greatroom, my feet would love to have a pair of Keen Calistogas in Rum Raisin.

  23. fishie says:

    I totally used to be the frugal shoe shopper. Oh yes! But now… I am thinking I need to find myself a ‘smart’ pair of foot (and body) friendly shoes. I love the Venture Suede or even the cute NAPA for work.
    I like this KEEN site… cool beans! Thanks for sharing !

  24. pendy says:

    I’d love the Stockholm boot. Wow. I tend to buy inexpensive shoes but they MUST be comfortable. My favorite pair is a pricey (for me) clog from LLBean. However, I’ve had them for probably ten years, so that works out to less than .50 a month. 🙂

  25. Andy says:

    I learned the hard way that spending on shoes is a necessity for my knees after standing for hours at conference and conventions display booths. I normally drop some change for Rockports with their steel inserts for support but I’d be willing to convert to Keen if they work. I pair of Bison colored Richmonds look pretty good. Thanks for the introduction to this brand.

  26. Kathy says:

    I am cheap with shoes. I’m cheap with every thing I buy for me and would like to branch out but am afraid to spend the money and not like the expensive stuff any better then the cheap stuff. And then I’d be out the money. But something has to give and right now its my back!
    I have issues!
    I’ve now studied the “Keen” sight. I’ve never heard of them before. I was really excited by what I read and am anxious now to read some “testimonies”.
    Winning a pair might be just the thing to pull me over into the world where, as one of your commenters said, a world where shoes become friends.
    My back would thank you.

  27. Junglewife says:

    The ones you picked are actually the ones I would pick, too! I love the clog/mary jane look! I think they’re called Berkeley clogs… 🙂

  28. Kathy says:

    OH MY! I forgot to put down the pair I’d like to try!
    “Wintrop clog”
    Slip on would be ideal and this one looks like it could take me from kitchen to carpool during Midwest winter with ease.

  29. Emily says:

    I think my favorites are the Palermo MJ’s. I buy both cheap and not-so-cheap shoes depending on how often (and how long at a time) I think I’m going to wear them!

  30. Megan says:

    I’ve been to the doctor twice this year for feet issues. I need better shoes, but I just can’t pay for them. I guess I need to start saving or something. Sell more tea wallets or something… I’d love this pair: The Palermo Mary Jane.
    Crossing my fingers here!

  31. Cheryl says:

    Wow! I can only choose one. I’d have to go w/ the Ridgeline, because I’m on a running kick, but I love all the mary janes.
    I’m pretty frugal, but if I can find good quality shoes on sale or clearance, I’d much rather buy something that’s going to last and wear well!

  32. E says:

    yes, yes, I do need this! I choose Sienna Ballerina! I have rheumatoid arthritis (all over) but have bad feet, ankles and knees and if I don’t spend decent $$ on my shoes, I just can’t function!

  33. mombrud says:

    I am in desperate need of some new hiking shoes. We love to hike with our kids and my old shoes are shot. I would love Wasatch Crest WP in Shitake/Ruby Wine.
    As for shoe shopping, I must be missing a chromosome because I HATE doing it and my hubby buys more shoes for me than I do. I guess part of the problem is that I need expensive shoes to get a good fit (I have weird feet) but can’t stand to pay the money so I just don’t!

  34. Kristin says:

    Oh, I love the sienna ballerina in coffee – adorable!
    I have recently changed my philosophy, and have invested in better shoes. If you figure cost per wear, a $100 pair of shoes that you wear several times/week is a great value (and great for my back!)
    My favorite brand is Privo by Clarks – I like to try them on at local stores to get a feel for the styles, then I go online and have been able to purchase them for HALF the price (“” is great)!

  35. Mindy says:

    I would love the BERKELEY but in black. Very cute. I’m of the philosophy of cheap shoes but my sisters have got me convinced that good running shoes are essential. I do buy expensive athletic shoes.

  36. Lori says:

    The Sydney II would be my choice.
    My shoe-buying philosophy is: if they have a “W’ after the size, are less than $20 and aren’t ugly, then I will take them home. (I have wide, stinky feet so most shoes don’t fit properly and I can’t bear to spend a lot of money on shoes that will quickly become profoundly odoriferous.)

  37. crystal says:

    I like a lot of the styles, but I kept going back to the pink and gray Ridgeline. I could get so much use out of those!
    I usually cheap out with shoes, but since I’ve started having back problems, I’m trying to go for quality. I pretty much live in athletic shoes since my chiropractor pretty much forbids me to wear flip flops!

  38. Jenn says:

    Ok, I’ll bite – Shay Boot. They look comfy warm.
    My philosophy, I can be mighty cheap most of the time, but there are a few things that it is worth spending the moola on. Shoes are one of them.

  39. mzzterry says:

    I choose the Wear Around MJ, In black. I have to have shoes that are good to my feet and my back…… I have MS, and it is important to my health, I learned this lesson the hard (painful) way!! I have never heard of this brand, they are very appealing to me, thank so much!

  40. Amy says:

    Oh, how I love the Berkeley! They are Mary Janes! And they have little daisy cutouts! What could be better! I wear size 11, so that limits my shoe budget considerably…since 11s are hard to find. I am pretty cheap, so I rarely spend more than $20 on shoes…but they had better be comfortable. (And, actually, I wear a 10.5, but that size doesn’t exist…except that I just found that it does on the Keen site. Who knew!!! They may have just won a customer!!!)

  41. stacie says:

    The Pallermo MJ’s are PERFECT for me!
    I am a cheapie shoe buyer. My shoes I wear every day are super old too. 🙂

  42. Alyson says:

    I LOVE the ones you posted, but I have so many clog type shoes I’d probably go for the same style but with the back (so the Mary Janes)… probably in brown. Those are so cute!!
    I’m generally frugal in my shoes – buying at PayLess or Kohl’s on sale (that’s where I always get my running shoes), sometimes Target or WalMart.

  43. Mandy/Mommy Cracked says:

    I love the Market Street shoes! They look super comfortable.
    I honestly didn’t used to care about quality shoes until I was diagnosed with Rheumatoid Arthritis at the ripe old age of 30. If I am going to be standing in them for any great length of time, then I have to have GOOD shoes.

  44. Minnesotamom says:

    I used to be on the super-cheap bandwagon, but then realized that it didn’t pay to have feet that hurt all the time to save a few 10s. So…now I try to buy quality (but if it’s on sale it doesn’t hurt!).
    You know, I think I’ve picked a different shoe for every one of these dern giveaways, but I’m going to have to stick with the one you picked – the Berkeley. I just wish it came in a color!

  45. Camille says:

    I would pick Sienna Ballerina in Port Royale. They look so cute and comfy!
    And I have always bought my shoes at Payless because I can’t afford good ones.

  46. karen says:

    Ooooohhh. My tootsies are begging you to draw my name! I need those great Shay boots, and I’d LOVE them in black. I don’t have decent boots–haven’t for about 6 years! Not smart, as I live in blustery Michigan!
    I’m a cheapo when it comes to shoes. But then again, I have yet to hit 30. 🙂

  47. Katy says:

    I really like the Ventura Suede, but can’t decide between the Pinecone or Midnight Navy.
    I love shoes. I really do. But I have a tendency to be way too frugal and buy cheapie shoes that turn out to be not so comfortable. I always shop for sales, and occasionally end up with a great pair of shoes, but I am in sore need of a good pair of casual shoes right now. I’m still wearing a pair of New Balance tennis shoes that I bought when I was pregnant with my daughter, who turns 2 in January.

  48. Lizc says:

    I like the Palermo Mary Janes or the Sienna Ballerinas. I am a believer in good shoes! So while I would like to buy cheap shoes, I know that good shoe are better for my feet, my sore heels, and my achy joints!

  49. Condo Blues says:

    I like the beet red Jaspers! I have munchkin feet, so I have to buy kid’s sizes. *sigh*
    As for shoe shopping I follow the John Waters rule, “Nice girls don’t wear cha-cha heels!” Guess who has a few pairs of cha-cha heels?

  50. Melinda says:

    You have some of the nicest giveaways. Thank you. I like the Calistoga, and the Palermo MJ, and the Barcelona MJ. My shoe philosophy? I don’t think I have one…. They need to be comfortable and cute. I prefer cheaper, but sometimes my 32 year old knees need support. Oh, and I want to be able to wear the same shoe for work or play. 😀
    Thanks again for a great giveaway.

  51. Michele says:

    I love the Calistoga Mary Janes! I am cheap, cheap, cheap when it comes to shoes! The cheaper they are, the more I can buy!

  52. Stonefox says:

    Wowser. I like the Saratoga II, the Calistoga, or the Sarasota. Seeing that I don’t have a single pair of closed toe shoes, I’d probably go with the Calistoga.
    I’m actually in the shoe shopping mode right now. Normally I go for cheap, but since being pregnant have learned that the extra support is worth it.

  53. Deb says:

    I have spent time on and off in the past 2 weeks trying on good shoes for winter. I generally buy a good pair of leather shoes about every 4 or 5 yrs but this time it has been longer because I can’t find exactly what I am looking for. I love the Keen Calistoga style for this winter. I need a great pair of comfortable shoes. I work in a library and I am on my feet the whole time I am there, w/out a great pair of shoes my back is screaming at me by the time I get home.

  54. Sarah says:

    I think I would choose the magenta Sienna Balletflats. Maybe not the most practical color, but definitely pretty!

  55. anna says:

    oh my goodness, how I want to win. I’ve been wanting a pair of keen mary jane’s for so long now! and when I went to check out their site, I fell in love with so many styles.
    please pick me. please??!! 🙂

  56. Staci at Writing and Living says:

    I like the Wear-Around MJ.
    My shoe philosophy? I’m a pharmacist. When I was in pharmacy school, an older and wiser pharmacist gave me this piece of advice: take care of your feet.
    Standing on your feet for ten and twelve hours shifts will make the vainest of twenty-two-year-olds go out and buy SAS shoes. Ask me how I know.

  57. kelli says:

    I go for quality – but I use coupons and watch for online sales to get good shoes for less. It works! And I definitely pay the money for good, stable running shoes.

  58. Miranda says:

    I’d LOVE to win these! My current everyday shoes are starting to fall apart. The frugal side of me cringes spending so much on shoes!
    The Palermo MJ’s would be my pick!
    bleucowgirl at hotmail dot com

  59. Laura says:

    I love Keen’s new Wear Around Lace shoe! It’s so funky casual, and socks are optional, which suits my lifestyle most def.
    I splurge on shoes, good shoes, for my kids and myself. Your feet need to support your frame for a lifetime, so I want them not only to grow well but also continue to be well maintained. If you do a little research about it, you’d might be surprised by how closely the two-our feet and bone health-are related. Pamper those tootsies. They will love you for it.

  60. wolfprint says:

    I would have a tough time choosing between the Winthrop boot and the Winthrop clog. I’m a hard to fit kind of gal and have been partial to Borne’s, but have always had my eye on Keen’s as well. My hubby and I consider ourselves frugal, but we never, never skimp on shoes. We would prefer to buy one pair of comfortable, good shoes, every few years (yeah, they actually last that long) than 10 pair that hurt our feet, knees and back.

  61. Jane says:

    I would choose the Palermo or wear around MJ. I love the idea of good feeling mary janes! It’s been too long since I had some Mary Janes!

  62. Carrie says:

    I’d love to add a pair of PALERMO boots to my meager shoe “collection”. I don’t buy new shoes until my old ones are falling apart but when I do, I always by higher end shoes. I’m all about my Dansko clogs these days and my current boots are Merrells. I’ve found that spending more on the shoes not only make my feet happy, it also saves me money because they last much, much longer.
    BTW – I also own an indecent number of sandals, for an Alaskan girl, including a pair of Keens I bought for our Ethiopia trip. (The best excuse to splurge ever!) The sun may not shine here very often but I’m all set when it does!!

  63. Kate says:

    Orion blue Calistoga, for awesome comfort and extreme cuteness — great with jeans, a denim jumper or a skirt.
    And I bet my orthotics would fit in them as well.

  64. Maranda says:

    You put up a good challenge! I think that if you are going to be constantly wearing that pair of shoes then the price is worth it. But if its just an every once in a while shoe then its not worth spending that kind of cash. For me tho I think if I were given the choice I would either get the Shay Boot in black or the Briggs shoe in the purple. Both look sturdy and the Shay boot looks like what I wear now only it has the sock already there. I would never have to worry about matching socks again!! MUAHAHAHA!

  65. Mrs. Pear says:

    I have to say, I looked around, and I agree with you! I love the Mary Jane style, and love slip ons – after all, we can wear them year round out hear in California without worrying about snow getting in!

  66. AndiK says:

    Oh, I love the Calistoga in seal brown! I need a pair of new shoes so badly! I am cheeeeaaaap…ahem, I mean frugal. But I’m learning to loosen up just a little.

  67. Kim says:

    I’d love the bronze green Jaspers. I think that shoes that fit you are worth the money. I’ve had badly fitting shoes before. All they did was sit in the closet. That wasn’t money well spent!

  68. Kel says:

    I love Keens! In particular, the Ventura line. I have a pair and they are extremely comfortable and durable. The chamonix look cute, too. As far as my shoe philosophy goes, you really do get what you pay for, so I spend a little more on my basic, wear-all-the-time shoes. I find that they last years, and my feet and knees thank me! If I get something trendy, I buy cheap. 🙂

  69. Christa @ No End in Site says:

    I like the PALERMO MJ, but I also love the ones you chose. I can’t decide. 🙂 As for my philosophy: I tend to be pretty cheap, too, but I do invest in one pair that might be a little pricier as long as it won’t go out of style soon. 😉

  70. The (Almost) Amazing Mammarino says:

    The Palermo MJ! I ruined my feet waitressing at Chi-Chi’s years ago and have to wear inserts in all my shoes now. I would normally buy the cheapest shoes I can find, but I have to shop for comfort. Even then it’s hard to find shoes that feel good.

  71. Teresa says:

    Oh I love, love, love those Mary Janes! Then when I looked at the site…they come in other colors! HEAVEN! It’d be hard to choose what color I’d want…but I could if I won!
    I usually by cheap shoes at Walmart…but I have spent money on shoes in the past (pre married/kids life) and they really stand up.

  72. Britiney says:

    Oh mercy!! How can I just choose one!!?? I’ve narrowed it down to three – the berkely, the palermo, the calistoga. I think the palermo would probably be my top pick for winter. I do tend to buy cheap shoes but my poor feet always pay the price. I do buy expensive running shoes. Somehow I justify that to myself. Thanks for the awesome giveaway!!!

  73. Melanie Lawrence says:

    Those there in the picture, I want those, they’re mine! My hubby spends tons on shoes and he has talked me into doing the same, but I just am sure to get all my monies worth out of them.

  74. Laura says:

    My husband is a big fan of paying for comfort, and he has converted me. Good shoes are worth it! I would love the Market Street Wear Around MJ. So cute!

  75. Kathryn says:

    I used to buy cheap shoes. Seriously, if I had to pay more than $15 for a pair of shoes it just wasn’t happening. And then the same thing happened. My feet hurt. And my knees. And my hips. I love me some frugal GOOD shoes though and nothing’s more frugal than free! I like the Sienna Mary Janes but really almost the whole Market St. line (except the boots) is good.

  76. kim says:

    I am loving the Mary Janes as well. I have never spent more than $20 on shoes (except running shoes), and the reason is I love shoes, but I don’t have the money to love shoes. So if I shop at payless, not so great quality, but I can have lots of them!!!

  77. AmyDe says:

    I have just a few pairs of very good shoes. Cheap shoes = pain and hassle. My faves right now are my earth shoes – mary janes. The keen shoes look wonderful. I especially like the Calistogas and the Palermo boots. Thanks!

  78. Cathy says:

    Oh this is an easy one for me – I’ve had my eyes on those Betty Boots in green since they first came out with them. I live in snow country and need good, cute boots SO bad…
    So yes – I’d LOVE to win this one…
    And as far as shoe shopping goes, I’m with you – the older I get, the more good shoes matter to me… I’m a big fan of Born shoes, as well as Keens, Clarks, Naturalizers… fortunately, these companies make good shoes that don’t look orthopedic, because I’m not ready to go there, thank you very much…

  79. kelly says:

    Seeing as how I desperately need a new pair of athletic shoes — seriously… They are at least 6 years old and falling apart. I have holes and cracks everywhere. They’ve been traveling too… Russia and twice to Mexico! But, I digress. My choice would be the Wasatch Crest.

  80. Kristen says:

    I love the Charleston Mary Jane.
    I have found over the years that it pays to have quality in shoes that you wear often and for extended periods of time. I have 1-2 pairs of high quality shoes and then some cheap ones.

  81. Tracye says:

    My mother in law has had a pair similar to the wintrop slip on in brown for years. She wears them all the time, and it’s time for replacing. I’d get them for her.

  82. Tresa says:

    Oh, what a fun giveaway! If I had to choose one pair, I would pick the Shellrock WP size 10 (women’s, of course)in black. I’ve just started exercising and eating right, and these shoes would be just what I need to stay motivated. Best of luck to all the commenters!

  83. Amy says:

    I like the Weararound Mary Janes but I could see my feet in many of the styles on that site! I am pretty cheapy when it comes to shoes…this would definitely be the most expensive ones I own (or have ever owned!)

  84. Jenna says:

    i love the weararound mj. so far, i’m cheap. like, $2.99 target flip flops cheap. and i live in them. so if i had more money, i’d buy better shoes. simple as that.

  85. Marian says:

    I like the ballerina flats. Just last week I resolved that, if it is at all possible, I will forever and always from her on out go for good shoes that fit reasonably, even if it means I only have a couple of pairs. Post pregnancies, I am a perfect size 10.5 (You know, the size the average company/store doesn’t carry or even make? “sizes 6-10,11”) That alone propels me beyond cheap shoes if they’re to fit.
    I’m a fan of clogs/mules for ease of slipping them on and off while wrangling kids and their paraphenalia in and out of the house. I’ve had a pair of GREAT Clark’s for 6 years of heavy use and, if I polish up the scuffs, they’re still in great shape. This fall I wanted a fresh pair and decided to go for a cute, on-sale pair at Kohl’s “to save money”. So what if they weren’t actually real leather,right?
    Two months later, the fake leather is already nicked and peeling, and they are obnoxiously hot to wear. They won’t last the season! So what’s really the better deal: $70 for a good quality pair that lasts for many years, or almost $30 for a pair that doesn’t even last a year and is uncomfortable during that time?
    (Please tell me you know all about Zappos?! The abililty to browse hundreds of shoes in minutes, free, fast shipping both ways, price matching– it’s absolutely awsome if you make the jump to good shoes!)

  86. Adrienne says:

    I want the sarasota for me and the Newport for my DD! 🙂
    My philosophy on shoes is buy one (or two or three) good pairs and wear them into the ground. This is not the area for me to skimp in. The pain makes me grumpy. 🙂

  87. Deborah G says:

    I love the Calistoga Mary Jane style, those would be my pick. As for buying shoes, I always seem to be last on the list for getting new ones. I tend to just buy a plain pair of white Keds (or knock offs)and a pair of black ballerina flats. Neither one is expensive, and by the end of the year, I need a new pair of both.

  88. Jen says:

    I have never heard of this company. I like the Berkley’s (like you) and the Ventura Suedes look comfy, too. What a generous company. Thanks!

  89. Becky says:

    Definitely the Palermo Mary Jane, in Coffee Bean. Beautiful! No way in the world would I pay $90 for it, though. I’m still at the cheap end of the spectrum, though longing for higher quality shoes.

  90. Rebecca says:

    LOVE the Wear around MJ in Moroccan Blue…since having 2 kids I spend more on fewer pair of good shoes since I’m running around & on my feet so much. Hope I win, thanks!

  91. maudie-mae says:

    I’d choose the Laguna in the Port Royal/Orange Ochre.
    Ninety percent of the shoes I buy come from the Munro factory outlet. I pay around $40/pair of shoes I buy and while the shoes I get are seconds, you sure can’t tell it. My mom got a pair of Munro Icons (retail for over $200) for $25 the last time I took her shopping.

  92. Cheri says:

    I would pick the Palermo MJ in coffee bean. I have very high arches . . . . since about 30 I haven’t been able to do the super cheap shoes. *sigh* So my life is full of expensive, yet comfy, shoes 🙂

  93. Lainie@ Mishmash Maggie says:

    The BLVD Ventura suede–I think I almost drooled when I saw them.
    I don’t have many shoes but the shoes I have are a pretty good quality. Both my parents grew up very poor and my Dad has major feet problems because he grew after his once a year shoe purchase. He was one of seven boys on a dairy farm and had to work all winter long in too small of shoes. His toes are a mess and he always taught us to buy good shoes.
    That and take good care of your eyes and your hearing!

  94. Jaz says:

    I would choose the Charleston Mary Janes. They look SO comfortable!!
    I tend to buy everyday shoes cheaply, and fancy, expensive dress-up shoes and boots. But now that I type that out, that seems backwards, doesn’t it? I mean, shouldn’t the shoes I wear every day be the most comfortable and nice?

  95. Jesica says:

    I am one of those that spend much for good shoes. Why buy a pair that is cheap and only lasts 3 months, when you can spend the money and have them last a very long time and make your tootsies happy. My favorite – Chaco sandals. They are like heaven for my feet. But, I hear great things about Keen and it would be wonderful to win the Palermo MJ, coffee bean, size GINORMOUS (well 10’s)

  96. Thatchermom says:

    Since I can’t order another pair of the four-year-old Jamestowns that are starting to wear out (sniff), I do think I love the ones you posted a picture of. Cute, and they fit the mom-with-a-baby-in-arms qualification of a no-hands shoe. Can I use any more hyphens in one comment?

  97. Robin from Israel says:

    The Amsterdams, with the removable insole. I was always a flip-flop and sandals girl myself (clogs in winter), but I’ve developed major foot problems and am now forced to start from scratch with “good, sensible” shoes (aaahhh!) that can take orthotics. Most, other than the KEENS, are shall we say, less than attractive, not to mention really REALLY freaking expensive!
    I’d love to win because right now the only shoe I can actually wear pain-free is my sneakers – not a great look when you’re trying to get dressed up!

  98. Jessica R says:

    I would have to go with either the mary janes or the ballerina shoes. I don’t spend as much on shoes as I should. I have the back pain to prove it!

  99. lolly says:

    I love the Betty Boot. It looks so toasty yet so cute.
    I am generally very cheap with most things, but not shoes. Bad shoes leads to bad health and disposition.

  100. Helen at A Work of Heart says:

    My mom would love you for this post…she is always telling me that I need to give up my cheap shoes and invest in some shoes that will give me more support. I could echo much of what you wrote…I now have arthritis in both knees and have learned the hard way that you get what you pay for when it comes to shoes…although that would not apply to designer shoes with the killer heels…
    If I could have my choice it would be something from the Market Street line…I love Mary Janes as well…
    Please Santa…pick my poor aching feet.

  101. margalit says:

    For this time of year, living in New England, I’m into the green SHAY BOOT. They look comfy and warm, the two most important things when I’m getting shoes for winter.
    I have HUGE feet, a 10.5 E, and I have a lot of trouble finding shoes. In fact, I wear Uggs all winter and birkenstocks all summer because nothing else fits and is comfortable. So shoe shopping is always challanging and mostly miserable for me.

  102. Pam says:

    I think well made comfortable shoes are worth paying at least a moderate amount for, for the sake of my feet and knees. I haven’t tried the Keens yet – these look wonderful- the red Palermo boots tempt me the most.
    Thanks for the giveaway! I hope that means they will give you some too!

  103. heidi says:

    I haven’t bought a pair of shoes for over three years…. Course, I’ve barely worn shoes for the past three years… anyway, the arroyoII looked good to me.

  104. Honor says:

    Ohhh, I love, LOVE Keen’s closed-toe sandals in red. My favorite! As for shoes, when I was working, I’d buy higher-end high heels, since they seemed to support my feet better. Now, I have my standby comfy and pricier shoes, as well as my cheap occasional shoes. I think quality and comfort are important, so am willing to spend more on my everyday shoes, but go cheaper on my special occsion shoes.

  105. Stretch Mark Mama says:

    Hubs rode our exercise bike in the same room as me tonight, and his kneecap popped WITH EVERY PEDAL. How am I supposed to write an article with THAT in the background?
    My daughter’s speech therapist wears those very shoes. I love them. I have been to shy to ask where she bought them. I know nothing about shoes so I knew I’d sound ignorant if she mentioned the name.
    Berkeley, before I forget.
    I own only a few pair of shoes. My lifestyle does not require much more than that. Everyone wears jeans to church (hello, rugged Pac NW!). But for my everyday tennies, I make sure to find something that’s comfortable and good quality. I just switched to Asics running shoes. They’re good. I’m rambling. Bye!

  106. TammiK says:

    I like the Wear Around Lace!
    I’m usually a pretty cheap shoe shopper. I buy a pair of $9.95 slip-ons at WalMart and wear then until they fall apart. But, when we moved to Hawaii I wasn’t able to replace my pair. During a trip to a neighboring island my shoes fell apart and I needed a new pair – fast. I stumble unpon a store selling Crocs. Who knew you could spend $50 for filp-flops. (But, they sure are comfortable!)

  107. Denise says:

    Most of my shoes are from Payless. I just can’t seem to spend money on shoes either!
    But I LOVE the Palermo Mary Jane in Coffee Bean (Brown)!

  108. Christine says:

    I love the Berkley’s in black. They look super comfy and as a fellow mom of 4 – you know how much running around we do. Spending a little more on shoes has worked for me. They seem to last longer and are better on my feet. Thanks for a great giveaway. Happy Holidays.

  109. Teri from Indiana says:

    Barcelona!! I worked in a shoe store in high school and then a year before I married. I wore high heels and the most uncomfortable shoes in the world…..for 12 hours a day. My feet are a mess. What my parents didn’t genetically bless me with ( Thank you for the bunions!), I took care harming the rest of the way. It’s comfort all the way now. I hit 40 & the stylish, uncomfortable, throw your back out went out the window. I did buy a pair of Hush Puppy dress shoes with a 3 inch heel. My kids thought I was having a nervous breakdown!

  110. Julie (Multitasking Mama) says:

    I buy cheap shoes too. Not because I necessarily want to, but because they are the only ones I can find that come in wide widths. I have very wide feet (some wide width shoes don’t even fit me). And as much as I love the Saratoga II shoe by Keen, I don’t think it would fit me.
    So, if I won, I would probably pick the Amsterdam for my daughter. Can’t go wrong with anything pink for her. 🙂

  111. Serena says:

    I like the Wear Around MJ. I love the Port Royale color, but I think the black would be more practical!
    I used to buy cheapo shoes, but then I discovered that it actually DOES make a difference to pay more and get a good shoe. Plus, when you pay more, the quality is usually much higher, so the shoe lasts longer, and it really evens out.

  112. Kristie says:

    Drool! The weararound MJ!!!!
    Shoes are SO worth paying more for. Cheap shoes have always made my feet hurt, even when they were 22 years old.

  113. Sarah says:

    I love the Sienna MJ in rust (orange) I need some bright, fun new shoes…pleeease (my birthday is coming).

  114. Beth/Mom2TwoVikings says:

    LOL I’m the super-queen of silly-frugal when it comes to shoes. One pair of quality tennis shoes every other year or so. I have one pair of Tevas and/or flip-flops for the summer. The last pair of leather-type shoes I bought was 7 seven (yes, seven) years ago. One pair of flats I wear to church…that is ALL!
    I’m kinda likin’ the blue Presidio.

  115. emily says:

    Oh, i do enjoy keen shoes. The palermo mj top my list right now. But, really, it’s difficult to chose.
    I buy quality. and that means that I have much fewer pairs of shoes than some, because buying food and paying bills generally get priority around here. My mom finally convinced me, just recently, that quality shoes were the way to go.

  116. Corey says:

    I would pick the black Ventura canvas for my husband (he currently has no “play” shoes).
    I am a big believer in not having “many” shoes, but in having quality for the shoes I have. Except for the kids, because they beat the heck out of them. Although I do buy them Land’s End winter boots because they get passed down from kid to kid so I want them to last.

  117. Rebekka says:

    I’ve always been a quality over price shoe shopper, but I wear an 11, so it’s hard for me to find cheap shoes in that size anyway.
    I’d definitely get the wear around mary janes!

  118. Rachel says:

    What an awesome giveaway!
    I’m a 20-something 4th grade teacher whose shoes look like they belong on the feet of an 80-year-old. I always go for comfort at school. Cheap and comfortable. I tend to go cuter and more uncomfortable on the weekends, but still cheap.
    I LOVE the Vail boots from the KEEN website. I need a good pair of winter boots. I haven’t “bitten the bullet” and bought a pair since my husband and I moved to New England 2.5 years ago.

  119. Lauren says:

    The Wear Around MJ’s are adorable!
    I am willing to spend a little extra when it comes to shoes that really need to be comfortable, shoes that I will wear all the time and for a long time. Cute little trendy shoes – Target, here I come!

  120. elizabeth says:

    I would love the very shoes you show. I have always been anti-shoe 😉 Preferring to not spend money on such things – until I hit my 40’s! GOOD shoes make a difference when a baby moves into walking, and so we should remember this for ourselves! I put everyone before me, even in the shoe department…
    I want to walk tall and straight into my 70’s, thus have begun wearing sensible shoes, and paying a little more money than I would like, but I, and my feet (whole body) are worth it.
    Thank you, Shannon – for continually – addressing all the essentials of everyday life in such thought provoking ways.
    AND thanks for the contest – IT is KEEN! ;P

  121. Kelly says:

    I like the ones you have pictured, but I also like the Ventura suede for my inner trying-to-be-a-surfer girl. (we used to live near Ventura, CA so I got all misty…well, maybe not)

  122. Rebekah says:

    I think I’d pick the same as you! I’ve always been a quality show buyer but was also tempted by the flipflops at old navy for years and paid dearly for it. I am back to my sensible, quality shoe buyin’ ways…

  123. Jess says:

    I like the Ridgeline or San Sebastien shoes. I tend to spend more money on tennis shoes but wear them until they are falling apart dead before I replace them. Dress shoes and boots I buy the cheapies. I figure it’s worth the $40-50 for tennis shoes when I’m only buying one pair every 3ish years….

  124. Trixie says:

    What a terrific giveaway! I would choose the Men’s Voyageur Mid (style no. 1257) in size 12. My husband would love a pair of these.
    Take Care,

  125. Laura says:

    The Winthrop boot is TOO cute. And now that I live someplace with winter, very tempting! This is a great giveaway. 🙂 I used to wear cheap shoes, until I got shin splints that took ages to go away. Then my mom bought me a pair of expensive but really comfortable shoes, and I was converted…

  126. Andrea says:

    I like the Palermo MJ. It would be fantastic to win – I love comfy shoes!
    My philosophy on shoes varies. I don’t mind buying the cheap ones from Wal-Mart that I know will only make it through the season. It bothers me when the “cheap” ones aren’t so “cheap” anymore. Shoes I have to wear in a wedding and probably will never wear again can also be cheap. When I went to Spain for an internship and knew I would be walking everywhere, I splurged on a pair of Clark’s sandals. I still wear them – three years later. I recently spent a chunk of birthday money (a big chunk) on good comfortable walking shoes for a trip to Israel. Other than that, I shop bargain racks and sales. I am not brand loyal on shoes.

  127. Lori says:

    I love the Calistoga. But I’m over my shoe budget for the year. The older I get, the more important I find it to invest in good shoes. I’ve been on a Clarks kick the last couple years, but this year I got some Merrells, and I rarely take them off. You only get one pair of feet, so you MUST take care of them!

  128. Elizabeth says:

    I like the shoes you picked out too! I personally feel like having one or two nice pairs of shoes are definitely worth it. My feet pay for it if I buy cheap shoes!!

  129. Leslie says:

    I LOVE KEEN SHOES! I used to subscribe to the super cheap shoe philosophy (and still do if they are shoes I won’t wear frequently). Then I found Keen’s and now I am among the converted. I own a pair of Keen flip flops that I wear every day during warm weather. I also have a pair of their water sandals that I love. This spring I bought a pair of the Barcelona shoes (in orange) and I get compliments on them all the time. I think now I want a pair of the Sydyney II but, honestly, I would wear ANYTHING made by Keen.

  130. Troye says:

    I love the Ventura in black for my kindergarten son. I bought him a pair of the Newports when school started, but he can’t wear them anymore because he had to start wearing prescription orthotics (sounds like a 90 year old man, right?). Anywho. I love Keens, but he needs a pair with a back now so that he can slide his orthotics into them.
    My shoe shopping philosophy is a mixture of both. If I am buying something trendy or something that I am not going to wear that often, I buy cheap shoes. If it is a pair that I will wear often, or that will not be going out of style next season, I will invest. But, I am also a pretty good bargain shopper and am able to shop for the best deal.
    Thanks for doing this!
    In joy, Troye

  131. Linda Sue says:

    Charleston Clog – because although I have NO urban lifestyle – they look very comfortable, I could wear them with jeans and my feet hurt – a lot. I would like to buy expensive shoes – have done so in the past – currently on fixed income so it isn’t happening in the shoe department! Take care of your feet – as you age the fat layer wears down (HONESTLY – I’m not telling a tale here) and no matter how rounded you are (and I are) your feet bottoms get thinner and the bones really take a load. Good shoes – very important these shoes you are showing are smart investments (and no bailout needed)

  132. carrie says:

    are they really as comfy as you say? if so, i may also have to break down and buy a pair. they look comfy, and the ones i thought would work for me were the wear arounds, or lagunas or the calistoga!

  133. mandy says:

    Love Love Love the Ventura suede in the BLVD line.
    I think shoes are important. We don’t buy SUPER expensive ones, but I’d rather have 3 good pair instead of 10 cheapos.

  134. Pat says:

    I like the Winthrop slip-ons, they look very comfy. I usually buy Clarks or Born, if they are on sale, both very comfy shoes.

  135. Michelle says:

    Genoa Peak WP in dark dull grey/wisteria! I buy big for sneakers (ever since birthing my first child, I think my feet flattened out and I need extra arch support). Everything else is bargain basement or discount rack!

  136. Lynne says:

    I am loving those pink Ridgeline shoes. Too cute 🙂
    I am just like you and never spend a lot of money on my shoes however, when I do I really think I notice the difference. Maybe I should re-evaluate my thinking!!

  137. Sherri E. says:

    Black Winthrop boot, no question. Because I love boots, and I love black.
    I am on the frugal side, although I do admit a willingness to pay above $110 for a pair of sandals when I was in college. They lasted me through 11 years of heavy wear, though, so at $10 a year I think the cost was justified.

  138. Danielle says:

    I love the Palermos! And my shoe philosophy is typically reasonable…I don’t like to spend too much on shoes because I get tired of them quickly. But occasionally, I’ll come across a good pair of work shoes that I think I’ll just pay more for because they are timeless and will get a lot of wear and tear!

  139. Jen says:

    It would be hard to choose between the Sydney II or the wear-around mary janes. These shoes are awesome looking!
    When I shoe shop, I go back and forth on price. I have an assortment of both. Cheap, flimsy flip-flops for running around the yard and house, and my stand-by birkenstocks for errand running etc. Same think with winter shoes–hand-me-downs from my mom for dress-up occasions and nice running shoes for working out.
    But, I’m with ya on the needing-better-quality-shoes for these aging gracefully bones of mine.

  140. AmyG says:

    Oh, I like the Wear Around Mary Janes! So cute!
    I’m cheap when it comes to foot wear. I can not justify paying $90 for shoes, period. And kids shoes? No way would I ever pay anything more than $10-15 for shoes. They out grow them so fast. Not to mention, they tear them up!

  141. Shannon says:

    I love their boots! Any and all of them.
    I’m a frugal shoe buyer. I also have big feet so I get most of my shoes at Payless. These days more places have the bigger sizes but for the most part Payless has always been there for my size 11’s.

  142. Lanie says:

    I would love a pair of Winthrop slipons in black. I am also very frugal when it comes to shoes. The most I have ever paid for shoes is $70 for my Ryka’s to wear to Jazzercise. A great investment, but painful to someone who rarely spends more than $20.00 for shoes!

  143. Nikki says:

    I’d go with the brown Marketplace. I don’t usually spend a lot of money on shoes – Target and Payless are my usual shoe stores. But I do have a pair of Dansko clogs that I wear almost daily during the winter (and have for the past 5 years). They were definitely worth the money!

  144. erin says:

    I love those berkeley clogs/ mjs, just like you do! They are so dang cute. My shoe shopping tends towards the cheap, but that’s because it’s what I can afford. I’d love to own a fabulous pair of expensive shoes.

  145. Jessica says:

    I love the Palermo MJ. I typically purchase cheap shoes, Payless and I are BFFs. However, recently I’ve had some trouble with my feet from not having enough arch support. I’m afraid of how expensive my shoes are going to be getting to get ones that don’t hurt my feet.

  146. Amy says:

    My shoe-buying philosophy is: are they comfy, classic, have a back to them (I live in New England after all) and black.
    I adore the Sydney II in black.. adore.. and they look so comfy!!

  147. amy says:

    I love the Timberline, Winthrop and Calistoga. Actually I love them all–so…….. And as far as my shoe buying philosophy- comfort and quality must be met. I don’t mind paying for comfort and quality.

  148. Carlyn Canady says:

    My shoe-purchasing philosophy is simple … if it costs more than $30, it’s not coming home … unless it’s tennis shoes. I am pretty picky about tennis shoes because I have to have support for my back. I have several clogs now that I wear that have very little support, but since they are slip on and not something I have to bend down and tie, they get worn more.
    My favorite shoe from Keen (at least from the website)? The Timberline in seal brown.

  149. Veronica says:

    I love the Palermo mary janes! I am a nurse and I am on my feet for large portions of time at work, so when it comes to work shoes I always shell out big bucks, otherwise my shoes come from Target.

  150. angela says:

    I too like the Mary Janes
    I like cheap shoes and always look in clearance. I unknowingly like Sketchers. I looked through my shoes and realized that 90% of my shoes are Sketchers. Boots, tennis shoes, sandals.

  151. Mel says:

    My shoe shopping philosphy is I have never met a pair of shoes I did not like LOL…too big put hose in the toes, too small just suffer!!!

  152. Ellen says:

    It would have to be between the Barcelona MJs, the Berkeleys, or the Amsterdams.
    My shoe buying philosophy varies. I typically try to buy more expensive shoes because I have found they are more comfortable and last longer. But I have noticed that I am getting less excited about paying the large price that comes with these. For my kids, I buy quality shoes.

  153. Grateful for Grace says:

    Ohhh, what great looking shoes. I like the Wear Around MJs or the Calistoga or the Berkley. The Betty bag is pretty sweet.
    I’m inbetween in the area of shoe buying. I believe in spending money to get a pair of shoes that will not hurt my feet, but I don’t usually feel comfortable going over $70 or so. I just feel guilty. If our income was more, I could probably increase the amount and decrease the guilt.

  154. Kathy C. says:

    I would definitely choose the Winthrop boot in Bison (size 8, hee hee). I am not a big shoe person, tennies for running, sandals, and a pair of basic pumps for dressy. I would love a pair of boots, but not one to spend the money on shoes for fun. 🙂

  155. Emily C says:

    I have always been entirely too cheap with shoes. Now that I’m a *real* adult (and have been for a decade), I ought to invest in some good footwear. I love the Saratoga II shoes–might even get them if I don’t win this giveaway!

  156. Jen C says:

    Palermo MJ in black, definately. I don’t pay much for my shoes, and I can really tell. If I’m on my feet all day, I wear my expensive running shoes, and can really tell the difference. I guess for shoes I go quantity over quality.

  157. CarrieJ says:

    I would get the Torino Lace shoes from the Market St collection for my husband. He has trouble finding comfortable shoes and those look like something he might like.
    My shoe philosophy is: I spend more on everyday shoes than I will on something I only wear occasionally. I find I do need more support since I’ve gotten older and I prefer to put my money into something I’m going to wear often.

  158. KarenDV says:

    Definitely the Winterport shoes. I’ve had the same snow boots for 15 years now, and I need something less clunky.

  159. Rachelle says:

    Wow! What great shoes. I am not usually a cheap shoes person. The winter pair that I wear now I have had for 4 winters in Minnesota. I would pick the WINTHROP CLOG or the Timberline. Hard to choose though as there are so many I like. What a great website. I book marked it. Thanks.

  160. Cindy says:

    I personally would pick the Women’s Trailhead Venice kind – they look so comfy and I love the colour.
    I love your blog. I’ve been shy about noting before, but I’m delurking here. 🙂

  161. Rita says:

    My vote is for the Berkeley in seal brown. My husband swears by his Keens. As for my shoes, I have my fun inexpensive shoes…bought when on sale…usually a great sale…and then I have my everyday “teacher” shoes…Clarks and Simples…I’ve been at home with my kids for seven years and most of my “teacher” shoes are still going. Does that tell you had badly I need a new pair of good shoes?

  162. Amy L. says:

    I would love to get the Bandon Shoe WP for my husband – he’s worn holes in the soles of his current shoes, but insists they are still good!

  163. Carey says:

    I am a buyer of cheap shoes as well, and not many of them. I just have a few practical pairs that go with everything and I wear them until they wear out. Purses – on the other hand – I can spend money on!
    I like the KEEN shoes! I would love to win a pair of the Calistogas in black. I like the pretty blue color they come in but they don’t go with everything!

  164. Sheila says:

    Okay, I love those Mary Janes and would love to choose them. However, it’s yucky winter here in Colorado, so I probably should choose the Chamonix Boots which also look really cool. 🙂 My husband and I both have their hiking sandals, and they are very well made. I am willing to spend more for shoes after my husband’s foot surgery. I still try to find a good deal, though!

  165. Ashley in Japan says:

    Hi! I would LOVE to own a pair of the Winterport shoes. I had to go from the “fun cheapy” flipflops to some sensible shoes while inport in San Diego. (I’m in the Navy) After walking around all day, my back and hips were killing me! (I just turned 27) I limped to the Walking Store and bought my first pair of Keen shoes. They are my go-to shoe. I can walk around all day in Japan and not be sore. Hooray for Keen!

  166. Dustin says:

    I’d get the Winterport, as I have no boots and now live back in a place that gets snow!
    Oh, and my shoe buying philosophy is to buy cheap shoes until I remember that cheap shoes don’t last that long / aren’t as comfortable and then buy a good pair of shoes that lasts. That cycle generally takes about two-three years or so to complete.

  167. Heather says:

    OOOOH LA LA- That Betty Boot looks so good right now while I am watching the news tell me about a winter storm warning! I am one of those dorks who wears boots to work and changes them there!
    We have been known to spend some $$ on shoes. I have wide feet and DH has narrow so in the long run it pays off. Dh is a lover of Naots… my brands vary. But a well made shoe does hold up! And I rarely have a closet full, just a few good ones.

  168. Jana says:

    I love the Sienna MJ shoes in the tan color. This would definitely be the most expensive pair of shoes I own if I won! 🙂

  169. lynn says:

    I love their winter boots and I need a pair. I only own about 8 pairs of shoes – so I definitely go for the more expensive but good-for-your-feet shoe. For years I only wore Birkenstock but I have been wanted to branch out and the Keens have always appealed!

  170. Christy says:

    I’d get a pair of the Ventura sneakers–actually i’ve been looking at them for a while and can’t convince myself to spend that much for them! I’m a cheap shoes buyer, too.

  171. Deb says:

    I love the Ridgeline, Black Olive/Baroque Rose. What a wonderful name for the color! I’ve never heard of this company; I’m bookmarking them.

  172. Wheezer says:

    I looove the Wear Around MJ! So cute! My philosophy is that it is worth it to spend $ on shoes that you will wear for a while like tennis shoes and good walking shoes but for the trendy shoes that you will wear for one season…Target here I come!

  173. Angela says:

    The Charleston Mary Janes are the ones for me! I have a friend who lives by Keens…I have stuck to Privos but I would love to own a pair of Keens too!

  174. mary says:

    Oooooh! I’ve never heard of these before and I love all of them. I think I’d pick the women’s Newport H2. I had a cheaper version of the same type of shoe this past summer and lived in them, so much so they fell apart at the end of the season. I’m sure a better brand would last much longer!

  175. Nancy says:

    I’m not frugal so much as cheap. I only but at the ultra cheap stores when they have SALES. My feet hurt too, plus the last pair I bought is just about down to the glue. I LOVE the Chamonix.

  176. Jaime says:

    I also love cheap shoes. Although one time I did buy a pair of $50 shoes and they have lasted me through many years. I guess that should tell me something.
    I’d love to win these. I love the Calistoga blue ones!

  177. stacy says:

    I love the Palermo Mary Jane because it’s “not fussy” but “curvy” like me!
    I don’t stress over shoes too much because the cutest ones never look that cute on my size 11 foot…sigh…

  178. Shelly D. says:

    Call me a copycat, but those Berkleys are crazy cute. You are right. I can’t think of anything better than clogs and MJs wrapped up into one! Basically I’m a shoe cheapskate. My kids always got striderite while I got Wal-Mart. I can totally relate to the joint popping!

  179. Keri says:

    Well Ive never heard of Keens. Yikes. But what awesome shoes. I’d love the PALERMO MJ. They look mighty comfy and come in either brown or black.

  180. Stephani says:

    I am always reluctant to spend very much on myself for anything. If I won I would choose the Palmero boots in Coffee Bean. They look nice and warm and I hate cold feet.

  181. Whitney says:

    I love, love, love the Chamonix boots. I’m a kindergarten teacher and I think these would look super cute at work or play!

  182. charlotte says:

    I love shoes, ALL shoes. So much that my husband has put me on a shoe ban. I am not allowed to BUY shoes, but I can WIN shoes.
    I like the Timberline or the Ventura suede. I really love so many.
    I hope I win.

  183. Rachel says:

    Winthrop boots, please. I don’t dish out big $$ for shoes, but have noticed that the more expensive kinds/brands last longer and feel better after a long day in them than the el-cheapo ones…

  184. Heather says:

    I have tons of foot problems thanks to over a decade of dealing with rheumatoid arthritis….at 41 I definately go for quality over price. Though I do so love a good bargin. I have two pairs of Keens, and they are fabulous. Even better, both were bargins….i have teeny tiny feet (some people have asked how they keep my upright)…one of my pairs came to me via hand-me-down from my 12 year old neice, they other pair were on end of the season clearance at REI….love those small feet.
    Both of those pairs are function over form, and I didn’t even know that Keen made such beautiful shoes….so i would definately go for the Berkelys in Black.

  185. Chris Wilson says:

    As a teacher, I am always on the lookout for cute comfortable shoes. The only ones I have found so far are Naturalizer. After looking at the website, I saw that there are a lot of cute shoes. I love the Waterfort black boots.

  186. Kari says:

    Just recently a friend and I were discussing shoes. She has expensive taste and I don’t. Mainly because I can’t afford them. She clued me in to her secret…Thrift stores.
    Just yesterday I found a pair of Born mary janes in Burgandy leather IN MY SIZE (!) for 2 bucks!!! They looked neverworn! I’m now hooked.
    I was really looking for shoes for my husband who works 12 hour days on his feet everyday. I think he would be stunning in these:
    Wear Around Slip On’s in Monkey Wood.
    Thanks for all you do!
    Kari B

  187. Susan says:

    I love the Palermo. For the most part, I buy cheap shoes, but I do have to have better quality running shoes…and no, I don’t actually run in them.

  188. cathy davis says:

    For the longest, I was a payless shoe gal. I mean, a girl has to have variety!! (Are there ever too many black shoes??)
    I’m at the 40 mark and I know my little feet and joints would certainly appreciate it if I would pamper them with some quality shoes.
    Personally, I love the shoes you have featured up there. Clogs/Mary Janes/& Comfort? COME ON!!

  189. Vintage Indie says:

    Oh Boy, I would love a pair of these. I love the BLVD Ventura Canvas, in Sahara Natural. These would be great for trips to the park!
    Shoes are hard for me, I have trouble finding ones that fit and are comfortable and look good. I like style, an affordable price and all of those things in one lead me to flip flops almost every time.

  190. Tara says:

    I’ve already perused the Keen shop for Big and Boo. Those MJs are my favorite!
    Philosophy? I buy what’s cute and cheap. I was living on the edge when I spent $20 on Walmart shoes late last summer. Yup, they’re already falling apart.

  191. Jane says:

    Tough choice – I think I’d go with the Briggs, Jasper, or Charleston Lace-ups. They all look so comfortable!
    Unfortunately my knees, hips, & back are paying dearly for the fact that I pay very little for shoes. I’ve never cared much about shoes, and shoe shopping is just plain torture to me. really. despise. it.
    My feet have changed size since my 3rd & 4th pregnancies, so I have trouble finding the right fit. And our weather (snow six months of the year) makes a sturdy shoe important. These KEENs look like they would fit that bill nicely.

  192. Jessi says:

    I also LOVE the Berkeley.
    My shoe-buying philosophy…hmmm, I guess it just depends on what the use is. I will most definitely spend good money (over $100) on running shoes. During my pregnancies, I experience a lot of back discomfort; and with my last baby, I discovered Dansko clogs and fell in love. I believe if you don’t have a good shoe, with good support, the mechanics of the whole body is “off”. Good supportive shoes are well worth the money, IMO…especially if you’re going to wear them a lot.

  193. Cindy says:

    I would love the Vail Boots.
    I have crazy foot issues that prevent me from being “frugal” with my shoe shopping. That is one area, where I have to go with comfort over price. BUT, I always find something comfortable on the clearance rack!

  194. Amy A says:

    I like the Palermo Mary Janes. My mom always bought us better quality shoes, like Rack Room over Payless. I don’t buy shoes very often at all these days. I find that a good pair of black and brown can get me through a few years. My mom did give me a CUTE pair of black clogs last Christmas that have my initials monogrammed on the top of them. I get compliments on them all the time.

  195. Candace (Mama Mia) says:

    I’m not really a big clog person, but I love Keen’s Mary Jane clogs- they’re so cute!!
    I buy cheap shoes and expensive shoes, but only when they’re on sale.

  196. World's Greatest Mommy says:

    These Palermo Mary Janes are my faves too.
    I never spend very much on shoes for myself. I buy nice shoes on clearance, or decent shoes on sale. And, I tend to buy shoes that end up putting my feet through torture the first time I wear them.

  197. Suzie says:

    Since I work in a gym, I would probably go for the ridgelines.
    I have been known to wear the same pair of shoes for over five years, but like you, I find I am having to reconsider my cheap shoe buying thanks to a lovely heel spur on my left foot.

  198. esscie says:

    I like the Palermo MJs.
    My philosophy: cheap is good for myself, but the kids wear out shoes too quickly, so LL Bean is the way to go since they’ll replace them as needed.

  199. Gina says:

    I like the Charleston clog in pinecone! I used to only buy cheap shoes when I had to wear dress shoes all the time (honestly, no pair of high heels are all that comfortable). Then I changed jobs and learned that a good pair of shoes is worth the money. Now I stay home with my kids, and I just don’t wear shoes that often.

  200. Aunt Murry says:

    I think I would have to have the calisto keen!
    My philosophy is good shoes at a bargin. If I want a pair I will wait for it to go on sale. I have long ago discovered a larger toe box and a brazilian made shoe fits my foot best. I always shop the clearence section.

  201. Rachel Silverman says:

    I would LOVE to win! I am somewhere in between on the shoe buying spectrum. If I’ve been looking for a certain type of shoe for a long long time, and haven’t found it inexpensively, then I’ll breakdown and pay full price. But generally, it kills me. Often I’ll just forgo that new pair of shoes, because I won’t shell out the money. I’d love to try a pair of Keen shoes – I’ve had my eyes on them for a long time!

  202. Jessica says:

    I love this pair PALERMO MJ! I too am a cheap when it comes to most things. I don’t think I have ever justified paying a lot of money for shoes. But maybe you are right, they could be worth it!

  203. Denise S. says:

    I would pick the Vail winter boots if I was so lucky to have my name drawn. I do spend money for good shoes and as you get older you definitely know why its money well spent.

  204. Christina says:

    I like the Calestogas. Super cute and I like the color!
    Shoe shopping philosophy: Spend a little more on the shoes I’ll wear most every day and then buy cheap accessory shoes. So far, it’s worked for me.

  205. Lois says:

    I think I would get the Winthrop in black;
    however, there are so many good choices,
    if I win, I might change my mind! So many decisions! What’s a girl to do?!?

  206. Lisa C. says:

    Barcelona MJs, I think. Or else wear-around MJs. I go back and forth on cheap/good shoes. I wish I could always buy the quality ones, but sadly the money just isn’t always there.

  207. Laurel says:

    The Waterfront Yogui would be my pick. We go bass fishing every summer and I am always on the look out for some good water/boat shoes.

  208. Julie A says:

    Cute shoe!
    My shoe shopping was always on the cheap side too! I worked at Payless Shoes for 2 years though so I got a discount on already cheap shoes 🙂 !!
    I like the KEEN Palermo MJ, really cute!
    Thank you for the contest!

  209. Tricia says:

    I’ve never seen these before. They look comfy and as I have gotten older, it’s harder to find shoes that don’t make my feet hurt at the end of the day! I like the Saratoga II or the Charleston Clog!

  210. Tracy Uebel says:

    What AWESOME shoes!!!!! I too, L*O*V*E the Wearabout MaryJane’s. Cute and comfy!!
    I’ll splurge on a good (costly) pair of shoes because I now NEED the support, as I’ve aged!! However, I only do this once every 5 years or so!!!!

  211. Lynn says:

    I love the Calistoga ones but I also liked the ones you showed us. I used to buy cheap shoes, very cheap shoes. Then my mother in law bought me a pair of really nice expensive shoes and I have never gone back to cheap ones. There is a difference in shoes. It is well worth getting nice ones, plus they do last a really long time. Much longer than cheap ones. I don’t buy real trendy shoes though. I buy basic classic styles if I am going to spend a lot on them.

  212. Jill says:

    I would pick the men’s wear around slip on shoes for my husband because the man works so hard on his feet and never treats himself to a nice pair of shoes.
    As for me, I can’t say enough about Dansko clogs. I have some serious blood circulation issues, and even some of those lovely joint issues as well; and I’m only 30! If you are just starting to hear the pop nearer to 40, your doing good my friend! Dansko shoes; you’ve got to try them!

  213. No No Nanette says:

    The sienna ballerina are my pick. I like all the color options in lots of the styles. Very cute – and a comfy shoe that isn’t a sneaker would most likely be a smart fashion step forward for me.
    And my shoe philosophy is cheap, cheap, cheap:)

  214. donna says:

    My feet require a soft cushion. I have to spend some money on shoes so I don’t have as many pairs as I once did. These look great; never heard of this brand. I love the Shay boot because when my feet get cold, I’m cold all over! Thanks for the giveaway! Donna

  215. Beth says:

    I’ve learned that good shoes last, so it’s worth paying a little extra. That doesn’t mean I always do it though. I like any of the clog styles – slip them on and go!

  216. Cindy Dukes says:

    I like the Palermo MJ. They are cute but look super comfy. I have worn out my brown leather clogs and need some new shoes, but I’m awful at shoe shopping. I love to buy clothes, but never get around to getting shoes until I wear them totally out!

  217. CajunNan says:

    I would love to have some of those Mary Janes! They are adorable!
    I’ve had problems with my feet forever and I have always had to spend $ on my shoes, but I’m cheap by nature, so I get “better” but not “best” shoes.

  218. LuAnn says:

    I would choose the peacoat Briggs. They looks so comfortable.
    I don’t usually spend much on shoes. I would like to be able to buy better quality shoes but there are always so many other expenses.

  219. Alli Crumley says:

    KEEN makes great shoes! Unfortunately, I’ve never been able to purchase a pair, due to cost. But I really believe they are awesome shoes. As someone who also has awful knees and a bad sciatica, I would love the Palermo MJs.

  220. Mandy says:

    Mary Jane Calistogo. About shoes, I am not picky because of my size enormous (11) foot. If they fit and are on sale, I might just buy them everytime.

  221. Marlise says:

    I really like the Berkeley. I’m a teacher, so I’m on my feet all day, and I love the thought of shoes that are cute and comfy. I usually settle for cheap and slightly painful.

  222. Nelly Feldi says:

    I love the Sienna Ballerina and the Amersterdam styles. They are great looking!
    I’ve always been super thrifty, but I’ve learned that good shoes are important (especially as you age). One good pair is more important than several cheap pairs.

  223. Liz says:

    I love the Winthrop boots! I don’t mind spending a little more for a really comfortable, well-made shoe.

  224. Samantha says:

    The Palermo Mary Janes are my favorites, but I love the ones you picked too. My shoe philosophy is that cheap shoes aren’t cheap any more when you’re having to buy anti-inflamatories, knee braces, or pay for surgery and/or physical therapy. We don’t do cheap shoes! Now, occasionally, I’ve been able to find something at a store that sells cheap shoes that has enough support and is well made enough to warrant giving it a try. But I’d rather own 2 pairs of nice shoes than 20 pairs of cheap shoes and it’s a lot better for me in the long run. And I would NEVER put my children in cheap shoes. The Striderite outlet has great prices and the shoes are worth it. They don’t know how to judge if their shoes are messing up their feet. It’s not worth the risk!

  225. pippi says:

    The sienna mary janes look fabulous. As far as shoe philosophies go, mine is “it’s hard to have a bad day wearing red shoes” my husband’s is “If your shoes or your underwear aren’t comfortable, you will be uncomfortable and cranky all day.”

  226. JessicaF says:

    I would probably choose the palermo mj. as I am in need of good closed-toed shoes, those look like they’d be versatile to go with a lot of stuff! 🙂 look deliciously comfy too!

  227. Shannon says:

    I would choose the: Palermo MJ. Oh so cute!
    As we are on a tight budget, my shoe buying philosophy is pretty cheap and on sale!

  228. lisa (lost pezhead) says:

    LOVE keen’s! i slurged and bought 3 pairs this summer and I’ve had my eye on the Portolas….I have plantar fasciitis and keens have nice arch support and are sooo comfy! i hope i win! actually i think i would get my husband a pair if I won, he needs to be converted, but he won’t spend the money on himself!

  229. Lisa says:

    There are SO many cute shoes! I have never heard of them until your post, so thank you!! My favorite would be GENOA PEAK WP.
    I have to say that I am truly very VERY frugal on shoes. If (and that’s a big if) I spend money on myself for shoes, it makes more sense to me to pay very little for them (usually in Payless) and be able to possibly get TWO pairs of shoes for the price of one pair somewhere else. Makes so much more sense to me, but I too, am having the same troubles more recently, in that I’m finding I have to have better shoes or my feet truly hurt. Thank you for this!!

  230. Carrie H says:

    I LOVE the Berkeley (same one shown!) and the wear-around MJ. TOO CUTE!
    I’ve recently realized the importance of good shoes after living on the cheap for far too long. I got a stress fracture in my fibula (actually kinda tough to do) as a result of running. My injury has healed, but now I can’t even wear my Skechers without feeling that old pain in my leg. I am now on a mission to only buy shoes with proper arch support. It would be great to get a nice pair like this for FREE:) Thanks for the opportunity!

  231. Becky says:

    Wow! this is neat. I would pick the Palermo Mary Jane. I like good but comfy shoes. I try to find mine on Clearance. I cannot always justify wearing expensive shoes. Thanks for this great giveaway!
    Merry Christmas

  232. Amy says:

    How can a girl choose? I love the Targhee II shoes. They look amazing! As for spending money on shoes, I just about have a stroke if I need to spend more than about $30 on a pair. I just.can’ That may be why my shoes wear out in no time, and my back hurts.

  233. jean m. says:

    The Winthrop Boot has been calling my name the last few days. I’m becoming very familiar with the Keen website with all the giveaways they’ve been doing.
    I very rarely buy shoes for myself unless it’s an absolute necessity, like say the office Christmas party. Even then, I pretty much got them free with the Kohls dollars I had.

  234. Ashlee says:

    I love the Palermo in tasty coffee brown! I am a frugal shoe shopper myself…unless I know it is a reputable brand…I don’t mind paying a little more!

  235. Carrie @ Three-Girl Circus says:

    I love all of their mary janes, but I’d probably pick the Charleston.
    I do believe in buying good shoes…ok, I’m a name brand snob. But I buy them at with several coupons and price match when I can too.

  236. Julie says:

    I like the same ones as you, but I like a lot of the men’s shoes as well. However with that being said, I can’t bear to spend that much on a pair of shoes. Yet when it comes to my kids shoes – I always spend money. I imagine as my daughter gets older, I may break down and buy her a few extra Target pairs that are cheap – but right now it is nothing but the good quality. I would hate to ruin their feet.

  237. Meshellyn says:

    The Charleston MJ would be my pick!
    For the most part I am cheap about shoes, and clothes for myself in general. I actually haven’t bought myself a new pair of shoes in well over a year, and they were a tennis shoe, on clearance at W*lmart. They were Dr Scholl’s though, so for $15 I felt I was getting a good deal for my bank account and my soles!

  238. TinaH says:

    I have terrible feet. (NO arch/bunions) I have always been so jealous of people that can wear cheap little shoes or even flip flops and look cute. My feet look terrible in them…plus it hurts. Feel lucky that you can wear cheap “cute” shoes some times.
    Keen is a great brand… are Born and Privo.
    I am loving Keens Palermo Boot–Biking Red! Wouldn’t that be great???

  239. Michele Laramay says:

    Oh, how I hope I win this. I live in Upstate NY. As in one mile from Canada. I would pick the Summit 2 boots. Although it would be a hard choice, as I love all the shoes too.

  240. Kirstin says:

    I’d like the Calistoga mary jane. I have a different Keen pair that I wear in the summer, and love them!
    I am moderate about shoes–I’m willing to have fewer pairs if the pairs I do have are nice.

  241. kelli says:

    Oh. My.
    I would totally LOVE a pair of “Napa” in “Bison”. THey look divine.
    With my balance issues, I need stable shoes now, and the $110 price tag for the ones the Dr. recommends? Yeah, not in this lifetime.
    I’m super-frugal. Payless is my friend.

  242. Elizabeth says:

    Oh…I want the Ventura Suede in pinecone. They look comfy and versatile.
    As for my philosophy, it depends on what I’m looking for. Athletic shoes, worth the money. Kick around shoes, not so much.

  243. Jocelyne says:

    My 41 year old knees would love a pair of palerno mj style 5452 size 7.5 in black..that way I could continue to chase my 6 soon to be 7 children in style & comfort!

  244. gretchen magruder says:

    I love the Mary Janes!!
    I am super-cheap, but in the last several years I’ve started buying fewer shoes, but better quality. I have 2 pairs of Danskos and pretty much wear them every day. Good shoes are worth the cost — though painful to purchase!

  245. Laura V. says:

    I would love to win the Calistoga in brown. They’re lovely and look so comfy.
    My shoe buying philosophy is to buy inexpenxsive shoes (Target, Payless, etc.). However, when I was still working full-time in a law firm and was required to look nice, I would purchase quality middle of the road priced dress shoes. It’s been several years since I’ve purchased any of those and the ones I have are still going strong, however, I’ve had to replace a few of my inexpensive shoes….

  246. Shelly says:

    I’m loving the pink Ridgelines! So cute. And I’m definitely a super frugal shopper when it comes to shoes …… Target is my friend!

  247. Crystal says:

    I used to be cheap about shoes but as I get older, I too, am forced to rethink that philosophy. For my daughter, I am willing to shell out a lot more money and I harp on her all the time about the importance of wearing the best shoes possible. What does she insist on wearing? Flip flops. These are the things that give one grey hair. I would love to win some Timberlines – and I promise I will wear them all the time! Thanks!

  248. Starr says:

    Genoa Peak WP.
    I buy cheap-o shoes and have even been known to buy them at Goodwill on occasion, if they look fairly new. (With lots of Lysol use once I get home.)

  249. Heather says:

    I’m with you about the cheap shoes. I shop at WalMart and Payless when I need a new pair of shoes. I’m currently in my 20’s, but perhaps I should change now to avoid problems later. I really love the palermo MJs. So cute and so versatile!

  250. Jennie says:

    I have slid down the slippery slope into men’s shoes. My feet are big and wide….not feminine at all. I don’ t like to pay more than $30 for shoes, and that higher price is for Nike tennis shoes. They’re the only ones that fit my “Fred Flinstone” feet. I’m a big fan of clogs – slide on & go is more my speed – so I like the Winthrop clog best. I need all that coverage to hide my cheap $1 socks!!

  251. Stephanie says:

    I also like the Ridgeline because they would be cute with jeans. However, I am in desperate need of casual shoes so anything would be wonderful!

  252. Leigh says:

    I am all about the Saratoga II. How cute are those?
    I literally just had this conversation with my cousin on Friday. When did I get to the point where I pass up shoes that are cute, but completely non-functional and uncomfortable? She says, “Face it, we’ve gotten old.” Ha!
    My shoe shopping strategy varies depending on what I’m shopping for. Cutesy stuff that I’ll wear once and blue moon, Payless, Target, WalMart, Kohl’s, wherever, here I come.
    If it is something I’m going to wear on a consistent basis, or at long stretches of time, I will gladly fork over the cash for quality and comfort. I spend a lot of time on my feet on concrete for work, and the two pairs of Red Wings (one boot, one shoe…a girl’s gotta have options!) were totally worth every penny I paid for them. Same thing with my Nikes I wear at the gym.
    They just opened a DSW near my office…this could be trouble.

  253. SherrieB says:

    I need a pair of casual boots – the Chamonix, Palmero and Winthrop all caught my eye, but I think I’ll go with the Winthrop. Love the detail in the back.
    As far as shoe philosophy, I am a “let’s find shoes on clearance at Payless” girl. I do love their Champion shoe line. I have recently changed to buying leather dress shoes (for church) as I have a very hard time finding dress shoes that are comfortable. (I have big feet.) They don’t necessarily last longer, but they are more comfortable.
    Thanks for the great giveaway!

  254. Sandi says:

    I love the Winthrop Clog in black. Thanks!
    I don’t usually spend a lot of money on shoes. The one time I talked myself into making an expensive shoe purchase, I had too many problems with them. They had to be exchanged three times! It wasn’t worth it.

  255. Lynette says:

    The Market St CHAMONIX in pinecone would be very nice! I only buy one or two pairs of shoes a year, but still don’t spend a lot of money on them.

  256. Howdy says:

    Hmmm that’s a nice deal! I have a pair of Keens and LOVE THEM… they are actually a ‘boys’ water shoe… and it’s nice to have a summer shoe to wear without the arch supports I have to use in everything else. Read that as I have to live in ‘walking sneaks’ all the time.
    Next on the list would be a comfortable winter boot… so I’d pick the Winterport. Oooooo I sure hope I’m random enough to win! LOL

  257. Fatima says:

    The shoes you like, the berkeleys, are my favorites too! I love a shoe you can slip on without tying…especially since I am perpetually pregnant (pregnant or nursing since August 2002!). I’ve never been a tennis shoe kind of gal and most dressy shoes go for looks rather than comfort. Let me tell you, comfort goes a long way when you are 7 months pregnant, carrying around a 20 month old!!!!!! I like cheap shoes too, but with all these little one I don’t have time for the search. I guess I get more practical with each addition to our family. Thanks for the contest!

  258. Sally says:

    We actually pay for shoes – I have well made Born shoes that are 5 years old & still running strong. The amount I spent is now less than if I would have purchased new cheap shoes with each new season. I do the same for my 8-year-old growing-like-a-weed daughter. She wears shoes that feel good & won’t take them off at the 1st chance she gets. They also withstand so much wear & tear. Her tennis shoes look a little worse for wear at the end of school, but it’s summer time (aka flip flop season) by then & we’re good with $1 flip flops for the summer.
    I’m so excited about the Keens! Haven’t heard of them & adore the Berkeleys.

  259. Sara says:

    I love the black Sienna Ballerina flats! They’d be great to wear to work…as a librarian, I’m on my feet a lot and walk around all day, and my comfy shoes (the current pair I’m always wearing were free, so maybe they don’t count) are quickly wearing out.
    I spend $$ on tennis shoes so they last in my day-in day-out use, but when it comes to cute shoes, bargain is best.

  260. Kate says:

    Oh I love the Charleston clog. After having my first real job and hosting an informational booth at a conference for 3 solid days my philosophy on shoes changed…there is a time and place that expensive shoes are worth the price.

  261. Lisa says:

    I would chose the PALERMO MJ. They would be something nice and practical for work. Also, I always buy the markdown shoes and I am very cheap. The few times I have gotten a good deal on some quality shoes and really enjoyed them I say I will pay for good shoes, but I can’t bring myself to it. So, I suffer with knee, back, and foot pain.

  262. Sheri says:

    I tend to be a frugal shopper, but am learning that the more expensive shoes last longer and are more comfortable. So in the longe run they’d probably be more expensive! I love the Palermo Mary Janes. Slip on and go, but very stylish!

  263. Rachel Boldman says:

    Wow, it’s hard to decide what I’d pick from KEEN. Right now it looks like the Siena Mary Janes are my favorite…but that could change depending on my current mood. As for my shoe-buying philosophy, it’s pretty simple: I don’t. That’s right, I don’t buy shoes unless it’s absolutely necessary. I’ve had the same REEF flip flops for 6 years and I’m dreading buying a new pair. The last shoes I bought were probably last February, when i was pregnant, and they were the same pair as another pair I had whose heel had worn down from over-use. They were $6.00 at Payless 🙂
    racheeb at gmail dot com

  264. Jenn says:

    I LOVE the water sandals!
    I coach rowing and my feet are wet most of the time. Sandals slip and sneekers squish…the Keen water sandals are so wonderful I’ve worn a pair completely out!

  265. Beth Moore says:

    Ventura Suede! Beautiful!!! And, I used to be the cheap shoe buyer too, and then I got “old” and decided that comfort was so much more important than having a load of cheap shoes. Honestly, I think I end up spending the same amount on shoes every year, but instead of having 10-12 pairs of cheap ones, I have 3 good pairs. One tennis shoe, one sport sandal, and one dress pair.

  266. Annie Jones says:

    I like the Palermo Mary Jane, but the Palermo boots are nice, too.
    My parents owned a shoe store growing up, so I always wore good quality shoes. Nowadays I practically live in New Balance tennis shoes, but I need something comfortable that will go with the occasional dress or nice slacks. I’d love to win these!

  267. mombo says:

    Palermo MJs for me! When my parents were buying, I had loads of shoes in all colors. Then reality hit and I had several pair of cheap shoes, mostly black. Then I got diabetes and the ensuing foot pain. Now I have very few shoes, not as attractive as I’d like, and expensive as well. Help a girl out!

  268. Rhonda says:

    I would do the charleston mary janes.
    And yes, I have gotten to where I buy “expensive” shoes. Not malo blancs (or whatever those trendy shoes Sex and the City raves about)…but Comfortable expensive shoes.
    I am sold on Born shoes, they last and are comfy (if you calculate the per year cost actually quite reasonable). I also like clarks, and would love to try memphisto and dansk..but since I basically wear either brown or black, and have born’s in each of those colors, its going to be a while before I buy another pair…
    I heart comfy shoes.

  269. MamaMay says:

    I know which shoes I would get for me… Strangely they are the same ones you would get for yourself….
    Seriously though, If I won I would get hubby shoes. We are in a real money crunch (he is in grad school and I stay home and raise 2 kids…) and he needs shoes that he can stand in all day. I don’t know his preferences but they need to look professional and sharp but comfortable.

  270. katherine from senior elefante says:

    ooo! am i in time to enter? i love the palermo mjs and the berkleys you pictured. what a great give away!
    and, i fall in between super-frugal and a splurger. if i know what i want, i try to be modest about it and find a good deal without sacrificing too much quality.

  271. Lisa says:

    I think I would like the Portola or probably one of the Waterfront styles. I think these shoes are pretty awesome.
    My shoe buying philosphy is all over the place. I’ll buy an expensive pair of dress shoes, if they fit and then hardly ever wear them. Or I’ll buy a $10.00 pair of ballet flats or flip flops at Target and wear them everyday. Go figure

  272. Stephanie says:

    I am such a cheap shoe buyer too. I really need to start investing more, but just can’t bring myself to do it.
    I sooooo love the Trailhead and the Winthrop clog and the slip-on. I may just have to have me some of those.
    I hope I win.

  273. Heather G says:

    I can’t decide between the Timberline or that maryjane you showed. I’ve heard great things about Keen shows. Would love to try them out! I tend to watch sales and DSW to get really good quality shoes at lower prices. Then I wear them till they are literally falling apart. I don’t have many pairs of shoes, would love lots more, because I can’t justify spending the $$.

  274. Kim in appalachia says:

    I like the Newport H2.
    Shoes are something I think it is worth spending the money on. My feet have always needed good support and I suffer when I have cheap shoes.

  275. Carrie says:

    I love the Mary Jane clogs also, so cute! I generally but cheap shoes. I’m a SHAM and how often do I need heals? Maybe once a year. I’m more of a tennis shoe kind of gal. Costco has great onces!

  276. Deanna says:

    I like the Charleston Mary Janes, although getting a good quality pair of tennis shoes or some winter boats are tempting too.
    I normally don’t spend much on shoes. I just bought a pair (my old ones were getting holes) and spent under $30.

  277. Tam says:

    For real, I would choose the wear around MJs. I go barefoot year around, but that looks like something I would not mind keeping on all of the time. Thanks for the chance.

  278. That Girl says:

    I’m not afraid to pay money for quality items so I would definitely pay for Keen shoes (and probably will if I don’t win!)
    I like the Charleston clog in Gothic Olive.

  279. Lesley says:

    I love the pair you picked out, too! I also like the navigator for my son. Goodness, I like them all actually.
    I am a super thrifty person. I can’t wear cheap shoes, though. I love to get an expensive shoe on sale!

  280. Betsy says:

    Oh, I really like the wear around mj in black!!! Hope I get lucky!!!!!
    It depends on WHY I’m buying shoes. If it’s a “two hour” shoe, as in I’ll only wear them a couple of hours to church or something, I buy SUPER cheap shoes… Target or PayLess all the way. BUT… if I’m buying running shoes or shoes that I need to wear and walk in, it pays to buy quality. Usually you get what you pay for.

  281. canadacole says:

    I love the Charleston. Like you, the Mary Janes speak to me, but I need a solid heel behind me or I walk right out of my shoe.
    My buying philosophy is to buy one pair of really great walking shoes and wear them just about everywhere, then get a few cheap fancy shoes for dressy occasions. I’m currently killing a pair of Doc Martins.

  282. L.A. says:

    I would go with the Charleston Lace. I find myself saying the word “sensible” as I search for good shoes.

  283. Jennifer says:

    THere are so many great shoes to pick from! My shoe philosophy has always been wait until the BOGO sale at Payless to buy any! With the exception of my wedding day shoes, my prom shoes, and a $100 pair of clogs that I bought in 8th grade and threw away my junior year of college.

  284. Kelli@CountryMommie says:

    I usually buy one pair of semi-expensive yet very comfortable shoes that will go with everything and wear them babies OUT! Or my Mother will give me the ones she doesn’t like (she has bad feet) and I can wear them for a while. I’ve never heard of KEEN before, so I will definitely turn her on to them. They look super comfortable and well made!
    You know… she would be able to try them on if I won a pair and see how comfortable they are {wink wink}.
    I really like the WINTHROP CLOG, in BISON (aka Brown).

  285. Jennifer says:

    I absolutely love the charleston maryjanes. I actually splurged about 6 weeks ago and bought me some Reeboks on sale at Sears, I buy shoes about once every 3 years and hope that they last. I never win anything, but I love this website for shoes. I will be going back there again!

  286. Tammy says:

    So many choices! I think I would choose the Berkeley, though there were a few others that made my list as well!
    I always buy cheap shoes, and my feet do not thank me for it!

  287. Katherine says:

    I had no idea there were so many great Keens out there. I have the women’s version of your husband’s shoe and love them for summer, but the Calistoga would make a great summer or winter shoe. I never realized I have a shoe-buying philosophy until you asked but I heard once that you spend a lot of time on your feet and a lot of time in your bed so invest in good shoes and a good mattress and so we do.

  288. Melissa says:

    I like the Palermo Mary Jane myself! It looks like a comfy slip on while still having a bit of heel at the back. I can’t wear true flats because of flat feet, so this one look like it would work very well. 🙂
    Melissa in FL

  289. LeAnna says:

    Oh. My. Goodness. I’m in love. I will be drooling over this website all morning, and might just leave the page with the womens Winthrop Slip-On’s up on the computer so my dear hubby will meander across them. You know there are only 2 weeks ’till Christmas, he has PLENTY of time to start shopping. 😉 Seriously though, I love their shoes! I’m a minimalist in regards to shoes, and have only a few favorite pairs. I’ve found the majority of them new, or nearly new at the thrift store, but when I do pay full price for a good shoe, I want it to last! My husband taught me that wonderful philosophy. He has shoes that are 10 years old and look like he bought them yesterday, all because he picks good ones.
    Thanks for the chance to win!!!

  290. Renee says:

    I love my Keens. You will not be disappointed.
    The pair I would go for right now is the Winterport Shoe. I need a really good pair of winter shoes.

  291. Angel/TaDaCreations says:

    Those look like wonderful shoes. I’d probably pick the Charleston Clog. I usually buy inexpensive shoes, or relaly nice ones at a discount place. But I’m usually at home in just socks or out and about in Crocs.

  292. Fiddledeedee says:

    I pay no more than $10.00 for shoes. And I get what I pay for. With pretty little bunions on the side.
    This giveaway is just what my podiatrist ordered. 🙂

  293. Annie P says:

    I love finding sales. It’s hard for me to spend too much on shoes when I know the prices will go down in a week or two.
    I loved so many of Keen footwear’s products. My favorites would have to be the Palermo mj or Palermo Boot, Chamonix, and Black Winthrop boots. I wish there was a store nearby that sold these!

  294. A&EMom says:

    Anything with a rubber toe would be the perfect solution for my daughter that seems to spend every waking moment scraping the tops of her good shoes on pavement.

  295. Andrea says:

    The stockholm boot the stockholm boot Ive had my eye on these babies for a little while santa be good to me, as I usually only buy shoes at Tarjey!

  296. Angie says:

    Oooh, the Mary Janes, definitely.
    I’ve always gotten cheap shoes, but I’m learning that paying for good shoes is definitely worth it. So now I split. Shoes I am going to wear a LOT I pay for. If it’s just fancy schmancy shoes I’ll only wear once in a while I buy cheap. And I love TJ Maxx for quality shoes at good prices.

  297. AmyW says:

    Sienna Ballerina – coffee
    I never buy any shoes unless they are drastically on sale. I’ve also found some sweet deals at the Goodwill.

  298. Snowbird says:

    Oh definitely the Sarasotas. I live on an island and go to the beach all the time. Plus I have the same knee, hip, ankle, back (you name it) problems that you do. These shoes sound like the perfect thing for me.

  299. Stephanie says:

    I love the Barcelona MJ in Chipper. I know it sounds gross, but I have had great luck finding brand name, almost new shoes at the thrift store. It’s amazing what people get rid of! But it would be great to have a new pair from KEEN.

  300. Martia says:

    I used to wear cheap shoes. Then, my sister started working at a high-end shoe store. Then, she made me try some Merrell clogs. And, my life has never been the same. She also recommended I try a pair of KEEN shoes. If I win the drawing, I’d pick the Timberline.

  301. Sharon says:

    I need the Palmerno MJ’s in the worst way! I’m a tight wad when shopping for shoes, and would love to try a high quality pair!!! What a treat — pick me, Mr. Random Generator !!!

  302. andrea_jennine says:

    Venice H2s for my hubby!
    For trendy shoes, I go cheap, because I only need them to last for a year or so. For classic shoes, I like to go to outlets and buy expensive brands at prices that are at least somewhat discounted.

  303. allysah says:

    I like the Amsterdam. They look so comfy. I rarely buy anything for myself these days that costs very much ~ there are too many other places to put it, but these shoes are very nice!

  304. Stacy says:

    Calistogas for black. I have extremely flat feet. I wore cheap shoes until about 25 and then I started having problems. Now I have less shoes but I pay a good bit for them. For dress shoes, I wear Aerosoles mostly. Now if I could just find a good pair of tennies for everyday that my feet really liked, things would be great!!

  305. Jennifer says:

    I LOVE the Pink/Grey Ridgeline! I never buy shoes for myself. Seems like with three kids, everyone is in need of something and shoes for me take the back burner.

  306. kellie says:

    I’m in love with the Sienna MJ. So cute.
    Shoes are one thing that I splurge on. My family all has bad arches, and mine are no different. I can get away without arch supports if I wear good shoes. They have to be ones that I LOVE, that are pretty neutral and will go with lots of things, fit exactly, and are from a good store with good service (who will take them back if I have any problems). I’m a huge fan of Clarks and Dansko, but I haven’t tried Keen yet – and I’ve heard good things.

  307. Cheryl says:

    I love the Winthrop boots in black. I am pretty cheap when it comes to shoes, too. But, as I get older…blah, I am looking for comfort more and more in shoes. I guess I’ll have to spend a bit more at times.

  308. Melanie says:

    I think I like the newport h2 shoes for summer, and I like your pick for fall/winter.
    I’m a big bargain shopper, but I do like good shoes. I wear a 10, and somehow it seems like the cheaper shoes don’t do as well in a larger size.

  309. Heather says:

    I’m super cheap, too. I have just this year discovered that I’m paying the price for it. I’ve been a Payless die hard for so long that it’s tough to break the habit. I love the Palermo Mary Janes at Keen!!

  310. Denise says:

    I have the same popping problem!! I LOVE the Palermo shoes in the bright green!!! Have never seen these before…will have to put them on my wish list! Thanks.

  311. michelle-this one's for the girls says:

    i looked for a long time and i still really like the ones you have photographed here the best.
    my shoe philosophy is to buy the most expensive shoes i can find on the dillard’s 70% off rack in february. and i have pictures of my shoe collection on my blog to prove that this is an annual tradition. spencer always buys me 3 or 4 pair of shoes for valentines.
    twoo wuv forever!!!!

  312. Elizabeth says:

    I am drooling over the winthrop boot. In college I was totally a cheap shoes girl. Now, at the ripe old age of 26, I have sworn off Payless and would rather have fewer pairs of quality shoes that don’t make my feet hurt.

  313. mrs. h says:

    I’ll pay top dollar for my kids shoes but I’m super cheap when buying for myself. If I can find a great pair of name brand shoes at Goodwill then I am over the moon happy.
    If I had to pick a pair from Keen I’d choose the Ventura Suede.

  314. Rachel says:

    I would choose the black Chamonix. We live in the snowy mountains, and those look warm 🙂 Thanks for the contest, I usually get my shoes from the thrift store…sometimes getting “good” ones that are just a little warn. I definitely prefer comfy feet!

  315. Amy says:

    That Winthrop Clog (in brown) is calling my name!
    I’m with you… I’ve always gone for cheap shoes. I pay $10-15 dollars, tops. And in the last few months I’ve been having hip pain, and discussing with my husband the theory that maybe I should pay for some better shoes. 😦

  316. Monique in TX says:

    Oh, Mary Jane’s all the way! The ones you picked out would make me happy! These days, I *will* pay a pretty penny for shoes, but for comfort and support, not for style. It’s a bonus when you can find both.

  317. Summer says:

    Well, first let me say that I like you take great pride in paying little for my shoes. I would rather have 2 $20 pair than 1 $40 pair. However, I am pregnant with my first long awaited child and am feeling the “pressure” on my feet. I would LOVE any of the styles but the Sienna (tan) and the Palermo MJ look great. The Sienna look very trendy and comfy….so, I am sure whoever wins, will be very blessed. Thanks

  318. Runningamuck says:

    I love any of the Mary Jane styles! I was almost sold on the boots too but they just weren’t quite there for me.
    I have the same theory on shoes… the bigger the sale the better. Especially if you have four sets of OTHER shoes that somehow are always managing to step, stomp and scuff up yours! =0)

  319. Tiff says:

    Oooh, love the Winthrop boot in black!
    I’m really cheap when it comes to shoes, only once have I ever paid more than $30.00, and that’s stretching it, sad, I know.
    I’d get down on my knees and beg to win this contest but they hurt too much from the crappy shoes I buy! lol

  320. Ann says:

    I like them all. I am looking for a pair of boots, so I would have to say the Napa boot would be my choice. I usually go cheap, but most of the time regret it.

  321. lizzykristine @ Uplifted Eyes says:

    The Winthrop Slip-on in Bison-color would be terrific for gardening and just stepping out of the house and driving and going to the store… well, it would be great for just about anything. 🙂
    I go barefoot as much as possible, wear cheap shoes when I’m only going to be on my feet for a few minutes, and wear Hush Puppies as a moderate-quality shoe for extended wear. I’m sure I’ll upgrade in quality as my knees deteriorate. 🙂

  322. Sarah says:

    I’ve got to go with the Berkely’s as well. Slip on but with the cute Mary Jane strap. Love the color.
    I am in FL so 95% of the time I am in $10 flip flops. Can’t beat it 🙂

  323. Autumn @ My MoonBean says:

    For me it’s a toss up, I like Winthrop boot, Summit County, and Ridgeline! They also have some cute baby boots!
    I believe is spending money on good shoes…like my danskos, they were worth EVERY penny. I wore them while I was pregnant (waiting tables) and my feet NEVER hurt! To me if you are getting quality then it’s money well spent!

  324. Nicole says:

    I’d like to try the Napa in Rum Raisin…although I do need boots!
    I think shoes are really important! I spend a moderate amount of $ on a good part of tennis shoes that I wear every day. I walk a lot and a good pair of shoes is a necessity! I yearn for the days when I can wear cute shoes again – and I’ll probably buy cheap cute shoes. But for now it’s ONE GOOD pair.

  325. Jen Sikora says:

    I can’t pick just one! I love the Centura shoe in Pine Cone for my daughter. I also like the Palermo for me.
    I tend to be frugal when it comes to shoes for myself, but splurge on my kids!

  326. AmyD says:

    Definitely the Palermo MJs…I am a sucker for Mary Janes, but I don’t have any in black! Plus, I’ve never had a pair of Keens….
    I am a Dansko convert. Two years ago, when I was 23 weeks preg with our second child, I fell and broke my foot. After that, Dansko Professional clogs have been my ever-present friend. (I also converted my husband and three friends, plus my mom who has plantar fasciitis…Dansko needs to hire me for advertising!) I have two pairs of clogs and two sandals. Well worth the $100+ price tag!
    A wise friend once told me that you should spend good money on two items: your mattress and your shoes. If you’re not in one, you’re probably in the other!

  327. Tonyia says:

    Oooohhhh….. I would love the the venturas or the seinnas, and I have to say that I usually buy reebok tennis shoes because the outlet store here has buy one get the second half off (all the time, not a sale), but NOW I work in an office and we aren’t allowed to wear tennis shoes. Well, I can’t afford to buy shoes like the other women, so I’ve bought what I could and my feet are paying the price!

  328. Kelly says:

    KEEN’s Napa is my favorite. And start buying nice shoes. Now. Don’t wait. I, too, had a closet full of cute, cheap shoes, some that went just with one specific outfit, cause hey, they were cheap! It is SO worth it to buy good shoes. I’ve been over 40 a few years now and have all sorts of foot, knee and back trouble, thanks to all those years of tooling around in cute, cheap, flat shoes. Merrell has been my shoe of choice – its all I wear now. Buy about one pair a year. But they really last. I hope to try those KEEN’s!

  329. rachel k says:

    I am loving the san sebastian in the blue indigo. I am so frugal when it comes to shoe shopping! Hubby believes in buying one or two good, quality pairs of shoes. I believe in having a selection, which requires frugality in our house.

  330. Miss Musing says:

    Ohh! I would love the brown Mary Jane’s! They’re so cute!
    I’m only 22 but I’m already all about the comfortable shoes. Years of cramming my feet into pointe shoes did a number of my feet and ankles. I prefer to buy comfortable, high quality shoes when they’re on sale!
    Thank you for the generous giveaway.

  331. kd says:

    The Timberline is my favorite. I’m happy to know about this shoe line…I’ve always been a Birkenstock fan. Talk about pricey! Gracious! BUT…they sure help my feet & knees. Am anxious to try a pair of Keens.

  332. Amy S says:

    I love the Portolas in green – and when it comes to shoes occasionally I splurge, but I have a store near me that has Designer shoes at deeply discounted prices most are display shoes. I have gotten a pair of $250.00 Stuart Weitzman shoes for $25.00

  333. Katie says:

    I think I’d pick Sydney II.
    A long time ago I used to buy certain really cheap shoes. I’d like them in the store, feel all smug paying for them. Then the first time I wore them my feet would hurt. The cheap shoes would sit in my closet until I forgot that they hurt… Then a few years ago I went to Europe and before I went I plunked down a shockingly large sum for some comfortable, versatile shoes. Best money I ever spent! Walked for miles with no chafing or blisters. They made all my other shoes feel horrible and they lasted several seasons. Totally worth every penny!

  334. Rebecca says:

    since the drawing is on my birthday I thought maybe I’ll actually win this time! 🙂 I’d get the ‘ridgelines so i can finally go hiking with my hubby . . .

  335. Jami says:

    My choice would be the San Sebastian in either color. I love that they go from a slip-on shoe to a sandal, and they look super comfy for hiking in. If I won, I may even go ahead and spend some money on a pair of San Sebastians for my hubby as well. He is in dire need of a new pair of sandals and hiking shoes.
    My shoe-buying philosophy: I have some cute cheap shoes, and I love my $3 flip-flops. But, if I’m buying a shoe I’m going to be walking in quite a bit, I’ll spend the money for the better quality shoe.

  336. Kathy says:

    I’m torn between the Palermo Mary Janes in a useful brown, or the Charleston Mary Janes in oh-so-fun orange….I think I gotta go with fun on this one!
    I usually cheap out with shoes too. But then I wear them until they pass out. What I need to do is find a nice shoe repair man and actually get some of my shoes re-heeled.

  337. Carrie in KC says:

    I love the Palermo boots and would probably never buy a pair for myself. I like to wear a variety of shoes, so I usually look for cheaper ones. Thanks for the fun giveaway!

  338. Linda Stewart says:

    I’ve had my eye’s on KEEN Footware for a long time now but I digress when it comes to buying a pair. I’m a cheap-o when it comes to buying shoes because I’ve yet to find shoes that I really and truly like to wear. I believe I was born to be barefoot … UNTIL I found out about KEEN. Now I’m ready to try something a little more upscale than bargain bought shoes. I have my eyes on Saratoga II in chipper. They look sooooo comfortable.

  339. Melissa says:

    I’m all about cheap shoes…why pay a fortune for something that only sees 2 inches above the ground??
    I love these Keen shoes! I especially like the Palermo Mary Janes and the Ventura suede shoes. Based on the price, I’d likely never purchase them, but winning a pair would be nice. : )

  340. Brian says:

    Every time I see this brand I make a bad joke about them being really keen shoes. I’ve always liked the look of them and would really love to have a pair. My current hiking shoes have been beaten to death so I’d probably replace them with a pair of the Targhee II model. When you’re talking about carrying a 30-40 pound backpack 20 miles you don’t screw around with cheap shoes!

  341. Kelly S.s says:

    Cute shoes on this site.
    I like the Ridgerock, pink hiking type shoe. Very cute. I am all about comfort!

  342. Need A Nap2 says:

    NEWPORT H2 in blue in a very small size. I need some comfortable sandals though I won’t be wearing them much with the cold weather outside!
    I shop around quite a bit when picking out shoes but I do want my shoes to be comfortable and am willing to pay more for that, but I’ll usually wait until a sale. 🙂 The most I’ve paid was for running shoes (I use the term running loosely, I don’t run, like ever!) $120 + $20 for inserts to raise my foot so my ankle wouldn’t hurt. I swear my husband about fainted when I told him how much. I’d already been to many many places and was running out of time (we were leaving for a trip the NEXT day). So now my goal is to spend way less than that less my husband disown me. 😦

  343. Robyn (3girlsmom) says:

    I’m loving the hiking-tennis shoe look. So I like the Trailhead Wasatch Crest. I can see some amazing hiking moments in those.
    Ok, let’s be honest. I don’t hike. However, I can see some excellent shopping moments in those.
    Just keeping it real.

  344. Vika says:

    I think I’d go for the Charleston Mary Jane.
    I buy shoes that will last and provide good support to my feet. So I don’t buy cheap. I like Danskos for winter, Chacos for summer.

  345. Lisa says:

    I would choose the Venice women’s shoes. To have a great pair of shoes to enjoy the outdoors in that would not require socks!
    I am a firm believer in good shoes. However, I also believe in only buying good shoes at a good deal. Barging shopping is a must.

  346. ran says:

    I’m into cheap shoes, even though my husband continues to encourage me to buy better shoes. So I have a couple pair of Clark’s that really are very comfy!
    I would pick the Sienna MJ in the coffee liquor color, though I would LOVE to have a pair of green shoes, but my frugalness tells me to stick with brown and black. The forest night Sienna MJ’s would be a real dream come true!!!

  347. Ashley says:

    I’m all over these ones: CHAMONIX BOOT
    I love boots! And Keen’s are the best ever!
    I actually buy expensive shoes. My mother believed in good shoes and I have passed that on. Sure, I own some payless shoes, but for real shoes, the kind I would wear every day, I buy both myself and my children expensive shoes. That might mean we each only have one pair of shoes, but they’re worth infinitely more than having a bunch of cheap-o, non-supportive ones lying around.
    And if you’re smart and know your size in the major, high end brands, you can often find great deals on ebay!

  348. Margie says:

    Saratoga II’s. Yes, it is very important to pay a little more for the comfort/support. Especially at 50+. 🙂

  349. Maribel says:

    As much as I would love to get myself the Palermo boot, I would prefer to get some shoes for my son…I love the Targhee in Dark Earth.
    Thanks for the chance to win one.

  350. Barclay Domier says:

    I agree with your pick or else the Portolas! As for me Payless or Target are my shopping places for shoes. Can’t spend much more than that on shoes. Plus if they do fall apart I just get to keep getting new ones! : ) My husband, believe it or not, differs in his opinion!

  351. Lori says:

    I agree, the Berkeley are super cute.
    I don’t buy many shoes, but I tend to pay more for the ones I do buy.

  352. Angel says:

    I’m also a cheap shoe person. Asking for a pair of Crocs was my biggest “name Brand” purchase of shoes in a long time. They were worth it, so maybe there is something to this quality thing. 🙂
    I like the Palermo MJ. Dressy enough to wear with nicer things, but still with pants. Thanks for the great giveaway.

  353. Mommy, the Human Napkin says:

    I think I like the Calistoga shoes in blue or maybe black. Or brown. I can’t decide.
    As far as shoe-shopping goes, I will shell out the money for some good tennis shoes because I wear them almost constantly. I’ve been wearing New Balance shoes for about ten years now, and LOVE them. This last time I replaced my shoes, I just got new ones because I was, umm, bored with my old ones. Is that bad? But for other shoes, I do tend to be a cheapskate since I don’t wear them that much, but I live in flip flops during the summer, so I usually buy about three pairs of the cheap-o, one dollar kind from Wal Mart.

  354. Jackie says:

    I really like the Wear Around MJ in Moroccan Blue (or black if I was being practical).
    My shoe buying philosophy is cheap for casual, expensive for work. Oh, and I always wear a cheap ballet flat or “ugg-style” boot into and out of work which makes me look ridiculous sometimes but saves on the wear and tear of my expensive work shoes.

  355. kristen says:

    Usually, I’m frugal when I buy shoes. Especially special-occasion shoes or only-go-with-one-outfit shoes. But I’ve learned that it’s worth it to spend a little more on my “everyday” shoes.
    Like anything in the BLVD collection, but probably the Ventura Suede.

  356. E-Jayjo says:

    I like the Barcelona MJ. I’m kind of in the middle on shoe prices. I don’t go for the cheapos, but I also don’t mortgage my home for them. 🙂

  357. MAG says:

    I would lovity-love the winthrop boot! Wowza, what a great giveaway.
    I don’t anything of quality in the shoe department. These would be a real treat!

  358. Kitchen Scrapbook says:

    Wow, this is a nice giveaway! It was fun to ‘shop’. If I’d win, I’d get the Market St Sydney II in brown.
    I mostly buy cheaper shoes, but once in awhile, I treat myself to a really good more expensive pair. It’s easier to justify having more shoes if I do it that way. 😉

  359. Lisa says:

    I too go with the cheaper shoes, but probably need to buy better shoes that will hold up and support my feet. I would have to get my daughter some of the Vail boots – so cute!

  360. Jennifer says:

    This is sooo easy…i’d get the Summit County Trailhead winter boot. It’s suppose to get below 0 this week and would come in REAL handy!!!! I’m a frugal shoe buyer which is why I’d have to either win this boot or Santa will have to be awfully good to me this year!

  361. Blue Castle says:

    I love the mary jane clogs that you have picked out! Those totally rock.
    I just spent $50 on a pair of shoes that regularly cost $80. It was a big stretch for me. I would love to get some good shoes as my feet are giving me troubles, but I just can’t get past the big price tag and the look of panic that I know whill come over my husband’s face when I ask him. 🙂

  362. Trisha says:

    I think that I would like the Barcelona Mary Janes OR the Summit County boot. They are great looking shoes. Thanks for the opportunity.

  363. Jenna says:

    I would pick the Calistoga in rum raisin – awesome!
    I tend to alternate buying good/moderate quality shoes at cheap prices, ie end of season clearance or Marshalls, with getting a few cute inexpensive ones for “light” wear from Target or similar. But so far I haven’t found a way to get Keens on the cheap (crosses fingers)!

  364. Laury Hoganson says:

    I am in love with two pairs, they look fabulous! I actually found it a bit depressing to window shop for shoes though. We were down before, but now the economy has BIT us in the bum very hard. I have eyed Keen shoes at our local REI store before. My brohter and SIL have Keen foot wear for their whole fam. They love them as well.
    So my top two are Wear around MJ in blue or balck and Timberline in black, or brown. The Wasatch Crest up were really awesome too though! They were my original top pick. Okay, maybe I can’t decide on one.

  365. Tami E says:

    I like the Mary Jane clogs as well as the Winthrop boots. I tend toward the more expensive shoes – they just last longer and are much more comfortable. I definitely go for comfort!

  366. nikie says:

    I love the Ridgeline. Pink and comfortable – sign me up. Keen has been the choice of my nine year old for years.
    Shoes are the one clothing item that I spend

  367. erin says:

    I love the Sienna Ballerina in coffee!
    I’m pretty cheap with shoes, except for the ones I teach in. Those need to be super comfortable, and usually “cheap” and “comfortable” don’t go together, so I may spend a little more on those. Otherwise, it’s Payless for me!

  368. Erica says:

    The Palermo Mary Janes would be perfect. I fell in love with these when I saw them. They’d be perfect for going back overseas where you take your shoes off when entering a home. As far as shoe philosphy, we always try to buy nice shoes even if they cost more, we just don’t have as many shoes. Our experience is that they last much longer usually 2-3 years and are much more comfortable.

  369. seussgirl says:

    So many to choose from, but I think I’d go with the Presidio – they look super comfy!
    My shoe philosophy has always been to go go cheap – after all, you can buy a lot of cheap pairs before you’d have paid for an expensive one. But since buying my Merrel clogs last year, that philosophy might need tweaking. 🙂

  370. Audrey says:

    I would pick the Ventura for a toddler girl. And shoes are definently worth shelling out some money for!!! In my opinion, most of the time, you get what you pay for!

  371. Molly Piper says:

    Because I live in MN, the practical part of me (who usually wins out) would choose any of the boots from the Market St. line.
    The wannabe funky part of me would choose the burgundy Amsterdam slippers. But then I’d only get to wear them for like 4 months of the year.

  372. Aubrey T. says:

    Palermo MJ is super cute and would be awesome for work, just like the berkeley. Please pick me!! As for my philosophy – as a physician I spend tons of time on my feet in the hospital, so I’m all about splurging on a few really, really good pairs of shoes. I have two pair of dansko’s, and one pair of borns that I wear basically all the time. They are not the cutest shoes, but my feet (and back and knees) thank me. The keens, though, would be both cute AND comfie – maybe I should just add these to my Christmas list.

  373. melanie says:

    Wow, what a nice item to give a way. It’s hard to choose a favorite…my top 3 would be the Charleston Lace, Charleston clog & Winthrop clog.

  374. Janelle says:

    I’d go with the black palermo mary janes. I do spend more money on shoes. I’ve found that if I buy nice shoes and take care of them they last for years and years. I just had to replace my 12 year old dansko clogs. I about had a heart attack when I spent $85 on them, but now they seem like a bargain at $7 a winter.

  375. Jennifer says:

    I would pick the winthrop boots in black. I used to be like you: Payless was my best friend. Why would I buy $100 shoes when I could get ten pairs of super cute ones at Payless for that money? And then I got a real job. And I cried and cried. And my mom bought me a pair of Eccos (ten years ago now! And I still love them!) to make me stop crying. And she was right. Now I love me the Danskos, the Eccos, and whenever I buy those cute $10 payless shoes, I look at them as only to be worn for short periods. And everyone is happy.

  376. Cathy says:

    Shoes are one thing I will spend on. I have flat feet and back trouble so need a good shoe or I pay for it in pain! I’d probably pick the Shay Boot right now, though the Wear Around Lace-up would be a close second. Thanks for the chance to win!

  377. km says:

    I need the VENICE H2. I like the Plum Kitten color.
    I can only buy quality shoes. I fell badly about 18 months ago and injured my knee. I’m just grateful that I can walk. My favorite shoes (my only shoes) are Mephesto, Dansko, Soft Walk, and hopefully soon Keen.

  378. Kelly says:

    I love anything in the BLVD line. They are totally heavenly.
    As far as shoe shopping goes, I’m all about buying good shoes. I spend quite a bit on my foot attire and find it’s totally worth it. Since I wear heels to work almost everyday, it’s important to have comfort. I don’t like the dogs to bark after a long day.

  379. Robin Byus says:

    I like the black and gray Betty Boots. It doesn’t snow here much, but I need some new boot for when it does.
    Oh, and I’m pretty practical when it comes to shoes. They have to be comfortable. I’m in love with Skechers right now.

  380. Diane says:

    Hi, I used to always buy the cheap shoes too, until I was about 47. In an effort to help back and ankle pain, I now buy much better shoes, even inserts ‘orthodics’, and have even sometimes added ankle braces. I love the Charleston Mary Janes.

  381. Libby Brill says:

    I think the Palermo Mary Janes are pretty darn cute! And they’d be even cuter on my feet. 😉
    When I am buying shoes that I know I am going to wear a lot, I try to buy better quality. Higher quality shoes wear better and last longer so, in the end, you spend less on one pair of nice shoes than you would on many cheap ones.
    But I can’t afford a closet full of expensive shoes. And sometimes you want a pair of shoes to wear with one specific outfit (so it will get limited wear) and that’s where the cheapos come in.
    So I have a mix of expensive and cheap shoes, depending on how much I plan to wear them. I guess it all boils down to cost per wear, which I like to keep low.

  382. Kimberly says:

    Those Berkeleys are fabulous. Some of those kids shoes are great, too!
    But I haven’t worn anything in three years other than birkenstock (sandels in summer, clogs in winter) and sneakers. Just bought myself a pair of fuzzy crocs for ‘slippers’ for around the house. Stylish, aren’t I?

  383. Everyday Mommy says:

    I own 7 pairs of Keens, yes I do. After ankle and foot surgery a comfortable and supportive shoe was essential. Keens are amazing and I love and wear each pair I own. My son also wears Keens.
    Don’t enter me in the give-away. I want someone else to enjoy a pair of Keens as much as I do.
    p.s. And, maybe the Keen folks would let me do a giveaway, too? Since I’m such a big fan.

  384. Melanie says:

    Charleston Mary Janes! Or everything else : )
    I’m a Payless girl, but I love Frye boots and will one day buy a pair when I get over the sticker shock.

  385. Melanie Bush says:

    I love the Palermo MJ…a combination of comfy and stylish (plus slip-on!). I normally don’t pay much for shoes and my feet are constantly “telling me about it”!

  386. AF says:

    I’d pick the Winthrop Boot! Since breaking my foot, I can’t wear a healed boot and that’s all I have. Previous to the injury, I was a cheap shoe fanatic! Now I know the value of “good” shoes…too bad they all have to be flat! LOL

  387. Les says:

    Oh my stars, I LOVE the Palermo boots. Even if I don’t win them, I think they will be mine. :0)
    I used to be just like you, Shannon. I had tons of CHEAP shoes, but as I’ve gotten older, it’s comfort over cuteness, and since I work in an office setting, I need nice-looking AND comfy shoes. So I like Aerosoles, Naturalizer, Nine West. I don’t by STUPID-expensive, and I always try to hold out until they’re on sale.

  388. Debbie says:

    I usually try to buy the cheapest, most comfortable shoes I can find – and this only once a year or so. But, what fun looking through what KEEN has to offer. If I won their generous prize, I would choose the Palermo Mary Jane to put on my 52 year old feet! 🙂

  389. katie says:

    Oooh, the Polaermo boots for me please!
    I pay the big bucks for shoes. They last longer and you end up getting more for you dollar (IMHO)

  390. Shani says:

    I LOVE the mary Janes that you show here, they are adorable! however with the winter weather here, I certainly am attracted to the winthrop boot. they look so cozy!
    I am a frugal shoe shopper. Mostly out of necessity, but also didnt see the need to pay more. But I do not wear shoes out. And would have some left from my jr high days if not for giving them to charity.
    But then I had a dughter and a son who are so hard on cheap shoes.. it has become worth the money to buy a little better built shoe.

  391. Amy says:

    I would pick the Presidio in brown. I am usually a cheap shoe girl but after owning a pair of their sandels I will spend the money on a pair of shoes at some point. They are the best most comfortable shoes I have ever owned!! Please please pick me!

  392. lomagirl says:

    I totally want the Calistoga or the Sydney II! I think buying a couple pairs of expensive shoes works better for me.

  393. tabitha says:

    I’m cheap but every since hubby got a pair of decent of shoes I’ve decided I need a good pair of shoes. I haven’t bought any yet but someday…
    I think the pair of shoes I’d choose would be the wear around mj’s.

  394. Kris @ Weird, Unsocialized Homeschoolers says:

    I like the Winthrop and the Ridgeline. I have mixed feelings on shoe-buying. When it comes to athletic shoes, I usually plan on spending a little tad o’ change because I know I’ll be wearing them for awhile. Also, I have plantar fasciitis, so I’ve got to have something taht supports.
    For dressier shoes that I don’t weare often, I’m usually cheaper. However, several years ago, my mom gave me a pair of Cole-Hahn shoes. Oh. My. Goodness! Those have been the shoes EVER! I would totally buy another pair of those…if the bank would give me a loan for them. 😉

  395. Claudia says:

    I love the Winthrop boot and the Calistoga. I used to be a cheap shoe buyer as well, but my husband insisted that I start getting better footwear, and there is just no going back.

  396. Erin says:

    I didn’t even know how much I wanted these. Thanks! I would love many of them, but I think the fav. for WI winters is going to be the Betty Boop.

  397. Brandy says:

    I would love a pair of those shoes. I usually buy my shoes as cheap as I can. Whether it’s at the thrift shop or at Walmart. My shoes can’t cost more than $10.
    I like the timberline clogs in sweet pea. It would be so nice to have a new pair of shoes.

  398. MommaBlogger says:

    I could really use a new pair of shoes. I have the hardest time finding shoes that fit me, and these are all so cute!
    If I got to pick, I might pick the Winthrop boot. I love the black boots that remind me of old fashioned boots that used to be worn. Plus, they’d look cute under my dress 🙂

  399. Clarissa says:

    I LOVE, LOVE, LOVE keens. I have 4 pair and will buy them again when I need more shoes. They are super comfortable and provide all the right support. If I could choose a pair I would get the Ridgeline since I am training for my first 1/2 marathon and I could use a good pair of trail running shoes.
    I used to buy cheep shoes, until I tried nice ones….. I’ll never go back. They are an investment, but they do last and they are specific for the activity, a big plus for your hard working feet.

  400. Christina K says:

    I love the Palermo MJs. Super cute and look comfy, too! I drift between buying cheap for infrequent use and prefer to pay for the higher quality for shoes that I use all the time. Either way, I would love a pair of Keen shoes!

  401. Crystal says:

    I love the brown berkeley! I have another pair of keens which I love!!! I love shoes – fancy, cheap, any kind will do! I used to buy more expensive shoes when I was working, but now that I am at home with my children, I have gone to cheaper shoes! But, the nice ones, like dansko and keen’s last FOREVER!:)

  402. Lynnet says:

    There are way too many styles, but I liked the Winthrop Slip-ons. They look comfy and stylish. I have a problem with regular shoes and have to get wides, but my feet are always cold. The write-up alludes to keeping the feet warm.

  403. Sara says:

    I’m thinkin’ I like the ones you picked out…. super cute…
    I’m frugal when it comes to shoe shopping (my husband would tell you otherwise, but I at least don’t spend $300 on boots at a whack… 😦
    I’ve come to the conclusion that higher priced athletic gear is a must if you want to have healthy feet and knees.

  404. Maren M says:

    I’d totally go for the Winthrop boot. Perfect for winters out here in Indiana!
    I’m middle of the road in shoe buying. If it’s a trendy pair of church shoes, go cheap because they’ll be out of style in a few months. If they’re a sturdy pair of everyday shoes, it’s worth it to pay a bit more for comfort and for quality.

  405. Pam says:

    I Love Keens!!! Currently my favorite is the Charleston Mary Jane style. I hope I win!!!
    I almost always buy well-made shoes but I try to get them on sale. The durability and comfort is worth it to me.

  406. Rachel says:

    Sienna Ballerina, please. If Keen has made a truly comfortable ballet style shoe I’ll be shocked.
    As for my shoe philosophy, I only have four pairs right now. The most expensive is three hundred plus dollars. I totally believe in quality over quantity. I know exactly what I want, why buy lots of “cute” when I just need a few good pairs?

  407. Jenifer says:

    I like the Berkley as well since I love clogs, too. But I’m also liking the looks of the Wasatch Crest WP. My husband has the same shoes as yours does, and he practically lives in them on summer weekends.
    The older I get, the more I’m willing to pay for a good pair of shoes that last, look great, and are comfortable!

  408. Jenifer says:

    I like the Berkley as well since I love clogs, too. But I’m also liking the looks of the Wasatch Crest WP. My husband has the same shoes as yours does, and he practically lives in them on summer weekends.
    The older I get, the more I’m willing to pay for a good pair of shoes that last, look great, and are comfortable!

  409. erin says:

    I would love to win–digging the Portola in Shitake! I have a newborn & a 2 year old so I’m in serious need of decent shoes. I typically buy one pair of really nice shoes & wear them til they get up and walk away! I’d rather have fewer pairs and better quality!

  410. Doris says:

    I want THAT pair! The one you posted! Same color, same style! Size 8.5 please! I love a clog and a LURVVVE a Mary Jane! Thanks! …and oh yeah, PICK ME!

  411. Jane Anne says:

    NO kidding, I have been eyeing the Mary Jane/Clogs for some time. I would pick the Berkeley in black or brown.
    My shoe philosphy is opposite from yours though. This is something I believe is worth spending $ on. I am not a shoe fanatic. I have few shoes. BUT, I buy better brands. They are more comfortable (I HATE uncomfortable shoes and they last 3 times as long. Brands that give me joy: Merrell, Birkenstock (and Barefoot), Privo and New Balance.

  412. karen says:

    Thank you for the great giveaway! I’ve never visited the Keen site. It was hard to choose! I am no frills when it comes to shoes because I am smaller in stature, but not thin. Big, rugged type shoes can look … well, a bit funny on me, so I keep the look clean and no fuss … no wild colors. Avoid chunky heels, on and on. I fell in love with the Charleston clog, pinecone color. Coming in second is the Charleston Mary Jane. My shoe philosophy, you ask? This is a short post – go look at this: . It. is. that. pitiful. I am wearing my mama shoes today – it’s near freezing. I just add lovely black socks. S.O.S.

  413. Joy says:

    I personally am a flip flop girl. I wear them 360 days of the year, wearing sneakers the other 5 for field trips or Disneyland trips, and then my feet kill being all closed up since they aren’t used to it. Guilty of even wearing cute flip flops to church every Sunday. They stopped looking at me an now just have learned to accept it. Good thing I live in CA where there is no snow. I do love the MJ clogs. I like to slip and go. And since I NEVER wear shoes inside (because I can’t stand wearing them, not because I want to prevent tracking in stuff), they would be great for slipping on and off at the door. I know I need better quality shoes. I get yelled at every time I go to the chiro (have had two back surgeries already) and he sees my cheap $5 flip flops on… “These can’t be helping your back!” Oh well, off to freeze my toes off picking the kids up from school in my comfy sequins flip flops, hoping to win a cute pair of Mary Janes.

  414. stacie says:

    I really like the berkeley ones. I like the idea of a clog…I hardly ever buy shoes and I end up going cheap at ross. I could really use a new pair of cute shoes!

  415. Blessed says:

    Um, I’d have to pick the Berkeley’s just like you did and for the same reasons!
    I have to wear good shoes – I’ve had knee problems my whole life!

  416. Kelli says:

    Hi All – Shannon this is an absolutely fabulous giveaway!! go you!
    I tend to not spend a lot on my shoes, because I just can’t bring myself to do it! The only shoes I spend what I consider a lot on is my gym shoes. My sister on the other hand, LOVES shoes and handbags and anything else she can spend her money on. She just had a baby a few months ago and if the baby was a boy, his name was going to be Keen. Yes – that’s right….named after a brand of shoes! Needless to say, Marley (not Keen) was born in July…and yes, she does already have a pair.
    I suppose I could be a good sister and say I would give them to her, but let’s be clear. I would totally choose the Winthrop clog…for me!

  417. MacKenzie @BRC Banter says:

    I normally go cheap on shoes but two years ago I bought a pair of Keen hiking sandals and I love them. But if I got another pair, I would go with something I could wear to work. I spend all day at a lab bench and need cute comfortable shoes like Calistoga, or really any of the mary janes.

  418. Josie says:

    There are so many cute shoes here…but the Sienna Ballerina would be my pick.
    My shoe philosophy? Fun shoes. I grew up with a shoe-repairman father who used to tell me that he fixed everyone else’s junky shoes, and he wasn’t fixing mine. So I had very good quality shoes and consequently not many pair. I longed for the cheap fun shoes. Now I have a mix of both. If it is a classic shoe that I can wear forever, I pay for quality. Otherwise it is cheap fun shoes for me.
    Also, I could never slip on and off shoes that tied. My dad had a FIT. Now I cringe when my kids slip off their tennies.

  419. Shannon in Texas says:

    I love the Ventura canvas–they’d be perfect for shopping, running errands, chasing kids, everything!

  420. heather says:

    I love the Palermo Mary Janes, and I am all over the gamut with how much I pay- some of my dress shoes for work cost 60.00 but some are only 10.00 clearance shoes.

  421. Kim says:

    I am in desperate need of winter boots. You see, I live in Utah, you know greatest snow on earth? Yeah, I don’t own any snow boots!!! So, that is what I would get. Or…some other fun shoes too. I love the Stockholm and Palmero boots. So nice 🙂
    Oh, and my philosophy is that when I have money to invest in good shoes I will. But for now, I can only afford the cheap-o’s 😦

  422. Shana says:

    I like the Palermo, but I also really like the ones you picked out…..and if I won, would be hard pressed to decide between the two.

  423. Amy F. says:

    The Winthrop boots are darling. I believe in good quality shoes. It is amazing how bad my back, legs, and feet can feel after wearing cheap shoes. I go to to try to get the best deals. Free shipping and free returns–you can’t beat them.

  424. Valerie says:

    I think the most I ever paid for a pair of shoes was $30. It hurt to pay that much. But I do wonder what it would be like to sink my foot into something like the KEEN Winthrop boot. They looks so comfortable. I have a feeling my feet would breathe a little sigh of relief.

  425. Andrea says:

    I like the Sienna Ballerina style. They are feminine AND functional! Awesome combo!
    My philosophy on shoe buying is buy quality for everyday shoes and don’t spend a lot on “extra” type shoes, such as heels for Mass or special occasions.
    I’m still young, only 25, so I feel like it hasn’t become that much of an issue for me yet. However, I have had 3 babies and I can feel how that has affected my back, hips, and joints and I’m thinking that with my next pregnancy I need to take the shoe issue very seriously.

  426. Stacy says:

    Winthrop boot FOR SURE!!!!!! I buy some cheap (Target) but am trying to make myself upgrage. ALWAYS spend more on workout shoes since they’re kind of important!

  427. Megan says:

    I try to buy good shoes, Nike, Rebook, Etc…but I wait until they are on super sale somewhere or at an outlet mall. I don’t spend more than 25$ for a pair.
    I really love the Sidney II, in brown.
    Great giveaway!

  428. Alice says:

    I love Keen shoes. I have two pair of the Sydney II and they are incredibly comfortable. I like the Timberline clogs…very comfy looking.
    I buy expensive shoes. I have wide feet and usually cheap shoes don’t fit well. I buy expensive shoes but not many of them and then basically wear the same 2-3 pair of shoes every day.

  429. anne f. says:

    winthrop clog in black.
    i’m more in favor of expensive shoes the older I get. I thought it was still OK to go cheap for special occasion footwear until I had to stand in seriously poor-quality heels for 30 minutes at a fundraiser. My poor feet were paying for days… maybe my stiletto days are just plain over regardless of the price category.

  430. anne f. says:

    winthrop clog in black.
    i’m more in favor of expensive shoes the older I get. I thought it was still OK to go cheap for special occasion footwear until I had to stand in seriously poor-quality heels for 30 minutes at a fundraiser. My poor feet were paying for days… maybe my stiletto days are just plain over regardless of the price category.

  431. Apryl says:

    I love the Palermo MJ.
    My shoe philosophy conflicts with my inner fashion diva – love the expensive shoes, hate the price tag, so I’m a gig fan of TJMaxx and outlet shopping.
    Thanks for a great giveaway!

  432. Helene says:

    I’d love the Charleston clog. As far as my philosophy–I usually buy cheap and only splurge now and then, but am also doing that more as I get older. I’m dying to try some Keens, though.

  433. Veronica says:

    I have never heard of these shoes…So cute though! I am loving the Calistoga Mary Janes, or the Berkley clogs! 🙂
    My shoe-buying philosophy…I love shoes! 🙂 But, I try not to spend too much on them. And, when I find a pair/style I like, I wear them until they fall apart! But, I am beginning to think that there may be something to spending a little more for a good pair…

  434. hannah says:

    gotta love the sienna mary janes.
    i’m a poor graduate student so i don’t have much of a budget to work with. but, i’d rather have one or two really good pairs of shoes that won’t hurt my feet and that will last rather than a lot of cheap shoes that required blister band-aids!

  435. Jen says:

    Whew, did I still make it? I love all the mary janes… how can I pick? Maybe the Charleston MJs.
    As far as philosophy, I’m a cheapskate at heart, but if there’s any item of clothing I’m willing to spend money on, it’s shoes.

  436. Tree Climbing Mom says:

    I’m a sucker for Mary Janes so I’d go with the Sydney II or Palermos. I’ve got terrible knees so I try to buy higher quality shoes – I just wait for mega sales before I do my shopping.

  437. Andrea Mitchell says:

    Don’t enter me, ’cause I’m Canadian and all, BUT if my knees are already bugging me at 32, what on earth am I in for at 40?!!! I wish I could win those shoes – crazy cute! I’m going to have to see if they ship here.

  438. Traci says:

    WOW! I have been wanting the Newport/Laguna type shoe. Not for the winter obviously, but for spring/summer! I have to say that I used to be able to wear cheap shoes, but the older I get, I find that I wear my shoes longer…so I feel I can buy a nicer pair of shoes. What a great giveaway!

  439. Chelsea Bass says:

    I really like the Sienna Mary Janes.
    I have cheap and expensive shoes. If I know I’m going to be on my feet for a while, I break out the comfy, expensive, not-as-stylish shoes. If I’m just going to church to sit for a while, I’ll wear the oh-so-adorably-cute-and-cheap shoes which I typically buy at Target.

  440. Mary Reading says:

    Since, I am the parent that buys good for the kids, and now all three kids have been outfitted with a pair of Keens in the last 2 months and I am wearing running shoe that I had many years ago.. If I could pick my dream pair it would be Saratoga II

  441. Lady in a Smalltown says:

    I absolutely ADORE Keens. I have 4 pair and am wearing a pair right now. My two favorite pair come from the Saratoga II line. The ones you picked out (Berkeley) don’t work for me, because the little bit at the back annoys my heel. I also tried the full heel pair (Calistoga), but they just weren’t right for me.
    But the pair I REALLY want? The ones I would buy if I won? The Betty Boot in Nile/Iguana. I tried on a pair the other day and they are so nice.

  442. Julia says:

    Barcelona MJs! I seriously thought I would be one of the only ones to want those, since my style tastes are usually about 5 years behind most people… But then I started browsing down the list of comments and well… looks like they are popular… Maybe I could be in style after all!!!

  443. Barbara says:

    I love shoes but have always refused to pay much for them so I never have more than 2 or 3 pairs. Doesnt leave much for the sophisticated work look i need, but I’m frugal. I splurged once on a pair of shoes for $75 and I will probably wear them till they fall apart (going on 10 years now :)). Oh and by the way I love the Palermo MJ’s.

  444. Ann says:

    my favorite are the wear around MJ. I don’t mind buying a pair of expensive shoes that I can see myself wearing with everything – I buy cheap if it goes with just one outfit!

  445. Hotomom says:

    I would definitely get the Sydney II in brown. Lovely pair of shoes. I have the same problem with my knees I need more of an arch support in my shoes but those usually aren’t very attractive unlike my friend the Sydney II.

  446. Kathleen says:

    Good shoes are definitely worth the money. I have some Keens that I love! They are 3 yrs old and still look great. I wouold love to try the Winthrop boot in black.

  447. heather says:

    I think the Calistoga shoes are very cute. They look Mary Janeish even! I think the Keen shoes are wonderful but I try to get them on sales!

  448. wanda says:

    I am a total shoe freak! I love them….and I love GOOOOOOOOD shoes.
    One of my all time favorites?? BORN & I love Josef Seibel too.
    It must be comfy and classic!
    I heart the Palermo’s and all the clogs at Keen.

  449. Tami Sickels says:

    I love them all but if I have to choose, I say the Saratoga II. Cute cute cute! I am pretty frugal (cheap) when it comes to shoes too. But lately I’ve had some problems. So if I win, now would be a great test to see if expensive shoes help. I love shoes and I buy so many it is hard for me to justify spending a lot on just one pair.

  450. MaryK says:

    I’d love to have the Timberlines in Beet Red. I love hitting the 75% off sale at the end of the season for better shoes.

  451. Patrice says:

    I love them and will go look at the real ones at some point
    Palermo – the mary janes you picked I love first tho

  452. Amanda says:

    Cute shoes! I would go with the sienna ballerina. I’m all about the slip on and go shoes:)
    I’m with you on shoes, I’d rather not spend the $$ on them, but I’m learning that maybe I should.

  453. April says:

    I like the Calistoga in Black. I also like the ones you like, any MJ you throw at me I will love. I used to buy cheap shoes but now I try to get the better brands cause they’re so much more comfortable when you have a 1 and 2 yr old like I do. I used to buy any shoes I wanted if I liked them when I was single but now that I’m married with a family I never buy shoes at the dept. store. If I see something I like I try it on, write down the brand name and style and search for it online for the most discounted price I can get and hopefully find a sale or discount code. I’m very patient also, I’ll wait and stalk shoes until they drop in price. I’m a big fan of zappos and

  454. Rachel says:

    I so want the Calistoga in blue. I’m in love….why oh why are they so expensive. I’d love to win. Pick me pick me…..jumps up and down wildly.

  455. jill jacobs says:

    TARGHEE II in blue/grey i think are my fave… i like a lot of them as i could use different keens for different purposes/weather etc. I think the Taghee would be practical for me though.
    I will pay good $ for shoes a couple of times a year (when needed for a specific reason like running/hiking/etc), but overall I like to find bargains so that i can have MORE shoes!

  456. Jennifer says:

    I love the Palermo MJ in espresso! What a wonderful looking shoe that also looks like it is comfortable. I also have knee problems and will need a replacement in a few years – a great set of shoes will extend my knee’s life!! 🙂 I am usually cheap when it comes to shoes, unless I think they will last and I can wear them for a couple of years.

  457. Kari says:

    I would choose the orange winterport.
    my philosophy. I stopped buying cheap a few years ago when my feet would everyday all day. So, I ask around of those that stand a lot and try for those. I love my Dansko clogs, a teacher friend of mine swore by them. Then, I met my crocs by chance and my feet have never been the same since. I try not to buy cheapies, and so, I don’t buy very often. My feet thank me, my closet thanks me, and even hubby is beginning to thank me!

  458. Sarah the secret blower says:

    Charleston Mary Jane in Pinecone…without a doubt…this site has cute stuff!
    I do occasionally splurge on shoes…splurge to me is 60-80 dollar range…because I am getting older…40 now…and I do like a good quality sneaker, I usually won’t skimp on those because I live in them…but I wait til they go on sale…smile..
    during summer, I resort to flip-flops…mostly for the value and convenience…a pair of Old Navy’s in your basic colors and you are set for summer living!

  459. Sarah at themommylogues says:

    I’d love the Winthrop boots in black! My shoe philosophy is mostly about quantity. I like shoes. I like them a lot. Always have. I like a sale, but if I really love them I might be willing to shell out good money. But never more than $100. I can’t even guess for you how many pairs I have. When I was in high school, a few boys used to call me “Shoes.” Why not Imelda, I’ll never know. And there is even a small child at church who refers to me as “the Shoe Lady.”

  460. Libby says:

    Wow! What a great giveaway! I change my shoe shopping philosophy based on what type of shoe I’m looking for. If it is something I’ll be wearing for a long time or will last me many years, I don’t mind paying for comfort. I find that when I try to shave off a few dollars, I end up with blisters! I really like the Sienna Ballerina in the camel color…they look so cute!

  461. Kris M. says:

    Oh…I would pick either the wear around MJ or the ventura suede.
    While I’m very frugal when it comes to food and beauty/health products, shoes are one of the items I spend money one. I own three pairs of diesels (each retailed for $80-$100 each – although I got each for $40-60). I also own many other shoes/heels for work…all of which are good brands and cost money, but well worth it. I normally only buy shoes if I have a coupon or they are on sale, but by doing that I’m able to get some good shoes for reasonable prices.

  462. Rebekah says:

    My husband works in a lab and I’d love to get him some comfy wear around slip ons. Personally, I buy expensive running shoes at least 3 times a year and it’s worth it.

  463. Kierra says:

    I would absolutely pick the Winthrop Slip On in Bison! I am just about to reach that point in my pregnancy when two things happen: a) I can no longer bend over far enough to tie my shoes; and b) The cankles make their great return and nothing is comfortable. These shoes look great because that stretch panel is simply calling my name, telling me that surely they would give way for the once slender ankles as they grow, even if I am on my feet all day. 🙂 That, and they are super stylish and would go with anything I would find myself wearing to work as a high school teacher.
    Comfort and style…what more could a teacher with a burgeoning belly ask for? These shoes would keep me happy, and keep my teenage students from laughing at my fat ankles AND ugly shoes!

  464. Valerie at Home says:

    I want those shoes, too! Of course, almost any of the others would be nice, but I love the slide-on factor of those mary janes.
    I have to admit to being one to usually cheap out on shoes, but I have come to appreciate a well-built (expensive) pair of shoes. My 2 pair that I shelled out the big bucks for are really the only ones that I wear now.

  465. Charly says:

    I like the Genoa Peak boots, they sound perfect for hiking in soggy Washington.
    I’ve started to spend more money on my shoes lately, and extra time. If I’m going to spend the money I need to be extra sure that I will actually wear them and they will last. So instead of having plenty of cheep shoes that I don’t wear, I have a few good shoes I wear to the ground.

  466. Suzanne Jackson says:

    I love the Berkley style — I think it would keep my feet comfy and cute while I try to keep up with my kids!
    As to my shoe-shopping philosophy… I’m frugal, but I define that as value for the money. If it’s cheap but not well made and not comfy, it doesn’t make the cut. I can’t imagine that I’ve ever spent more than about $80 for a pair of shoes though, as I try to catch sales.

  467. Kelley says:

    I’ll go with the BARCELONA MJ in a size 6 please! So cute! (if you don’t like my Guam address, you can send them to the parents in MS)

  468. JenS says:

    Since my *favorite* 9 years old pair of Bass clogs just fell apart (my husband thinks something actually ate the inside of the sole!) I’d love to have a pair of the Palmero MJ or Berkeley clogs. I love the detailing on the Berkeley, which is is one of the things I loved about my Bass clogs, besides the comfort! 9 years, $36 on sale…can’t beat it. Comfort over cost for shoes any day.

  469. Erin says:

    The Charleston Mary Jane looks so comfortable and stylish.
    I love to get a good deal on a pair of shoes, and trying to avoid foot torture, have begun shopping the department store close outs at the end of the season. I don’t mind paying a little more when it means a lot more comfort. My nine year old daughter likes to remind me that my shoe size doesn’t change like hers does.

  470. Dawn says:

    Being 6 months pregnant and working 2 jobs where I am on my feet A LOT, shoes have become something I will invest a little more in. I love the Barcelona MJ and the Palermo MJ!

  471. Milehimama says:

    Oh Shannon, a comfy shoe giveaway??? How absolutely wonderful!
    I have terrible problems with my feet – right now I’m wearing Avia walkers with THREE different inserts in them – and cute shoes just aren’t happening, it seems. (I’m only 30! Why do I have to wear old lady shoes?)
    I’m scared to buy shoes anymore – they never seem comfortable. I’d love to try a KEEN!
    Especially the Palermo MaryJanes! So cute for church!

  472. CarrieO says:

    I’m more on the frugal side – although I have bought higher priced shoes a few times that have really been worth the money. I really like the Sienna MJ’s in orange. Although that would pose a matching problem, but who cares? They’re fun looking!

  473. Rachel says:

    I love a couple of different pairs of the boots – and most of the mary janes – it would be a tough decision but I would try real hard if I won!!

  474. Brooke says:

    i try to by good brands at discount prices (like at TJ Maxx). i’ve found that nine west heels really do feel as comfy as flats.
    the sienna ballerina is my favorite! 🙂

  475. Margo says:

    how cool! I’ve never owned Keens but I’ve heard good things about them. I have big feet so I’ve always been forced to buy expensive.
    I would choose the Women’s Presidio in midnight navy or the Portola in Shiitake because I could the cool mom and still get around town.

  476. Jessica says:

    I love several of the shoes. One that I think I would wear just about every day though would be the Charleston Mary Jane in either rust or pinecone.
    I am an in between shopper when it comes to shoes. I usually end up with pricey shoes but wait until they are deeply discounted.

  477. Kimberly C says:

    I used to run long distance before the kiddos came along- so my ol’ feet really appreciate good footwear. I’m really impressed by the selection they have- but I would go for the Winterport Shoe. They’d be perfect for going on hikes with the kids!

  478. jen says:

    Actually, I LOVE the shoes that you have pictured right up there, the Berkely, but I need new winter shoes – something with a back. So if I won, I’d probably get the Calistoga or the Winthrop clog or the Amsterdam; they are all so great!!!

  479. Dana says:

    I like the Berkeleys like you pictured, They are my FAV! I have rarely buy myself shoes, so if I do I get decent ones. They are worth it.

  480. allyson says:

    i think i would pick the sienna mj in green..
    i don’t mind spending 50 bucks or so on shoes, depending on how much use they will get. but i do wear flip flops, generally cheap flip flops, almost exclusively in warm weather, which i know is supposedly terrible for you.

  481. Kristine J says:

    oooh. though call. I love the Palermo MJs, the Calistoga and the Charelston MaryJanes I think if I won, I would have an incredibly hard time choosing!

  482. Emily C says:

    I’m digging the Sienna Ballerina. Not sure which color, though.
    My shoe philosophy? I’ll spend between $30 and $60 for a pair of shoes, but I expect them to last for at least two years. At any given time I’ve got a pair of heels, a pair of dress sandals, a pair of boots, and a pair of tennies. That’ll do me.

  483. Asara says:

    Hi! A friend of mine shared this contest with me, and I couldn’t resist entering. I would have to pick the Sydney II in navy. I need my shoes to have a back, or else they pop right off.
    My shoes.. I generally buy at Payless, the cheaper the better. When they wear out, hey, I didn’t pay a lot for them, and I won’t pay a lot to replace them!

  484. Pam says:

    The palermo mj looks adorable and comfortable. I’ll pay more for comfortable shoes. It’s very hard for me to find shoes that fit.

  485. Kansas Mom says:

    I tend to pay for shoes because I have huge feet and have to order or buy early (usually order, most stores don’t carry many in my size). I loves shoes and would go shoe shopping all the time if I could (so perhaps it’s a blessing I can’t find my size).
    I don’t have any boots I can wear outside in the winter and have really needed some for about three years. I love the KEEN Stockholm in black!

  486. whitney says:

    I’m digging the Mkt.St. Saratoga II in Chipper. I have a bad knee too:)
    I never skimp on shoes. I have found that good shoes are so worth it. To me it is better to have one or two pairs of good shoes that a pile of cheap ones:)

  487. Erin says:

    I would pick the Ventura Suede. Living in Florida, I own way too many pairs of flip flops and after a while, even the “expensive, hoity-toity” ones make you feet and everything else hurt!

  488. Jacque says:

    I’d choose the Palermo MJ. I would rather have expensive, well made shoes, and cheap clothes than the reverse.

  489. Brandee says:

    While I have never owned a pair of keens, I have always been envious of my friends who do. They always talk about how comfy they are yet still stylish. I’m pretty frugal when it comes to buying shoes or I think I would own a whole closet full of keens. At this point I would pick the Winthrop boot because I’m looking for a good pair of winter boots especially since I’m 7 1/2 months pregnant and have to, I mean want to take my 80 pound dog for a walk EVERY day regardless of the Minnesota weather.

  490. susan says:

    The Shay boot is adorable! I have a horrible time finding shoes that are cute and comfortable and in my price range. I hate spending money on shoes, but I’ve recently decided that it’s worth it for my toes to be comfortable.

  491. Sylvia says:

    I love the palermo mj’s in coffee bean. As I get older I find myself spending more on shoes. I also find myself buying wider shoes–no one told me pregnancy made your feet wider. Sore feet make me crankier than normal, so it’s worth a little extra!

  492. Pam says:

    Maybe it’s because I’m so cold right now, but I’m really diggin the Winthrop boot.
    I would seriously spend that kind of money for a shoe that looks that good!

  493. Jomama on a Llama says:

    I’m in my tweties still, and *was* a flip flips and cheapie shoes type of girl until my ankle and knee vigorously started protesting. Keens are anti-cheapie shoes, and I would love a pair of the Palermo boots! Rockin’!

  494. Beth says:

    Oohhh – I have to say Calistoga. I’m sure I could find lots of uses for any of the colors, but the Orion Blue or Rum Raisin are my favorite.
    As far as my shoe-buying philosophy, I’m willing to spend a little more (about $50, which I know is nothing for some people!) for a few staple pairs that I know will take a lot of wear and tear – running shoes, a pair of black heels for work, maybe one nice pair of boots. Anything that’s a funky color or more trendy comes off the clearance rack or from a discount store.

  495. Kim says:

    I have had plantar faciitis on one of my feet, in addition to heel spurs on the same foot. My doctor (who had the same foot problems) recommended Dansko shoes. I had to save my $$ for them since I usually don’t spend more than $20 on shoes (and Danskos are around $120!). But they were worth it for my sore feet. I’m now on my second pair, but they last about 2-3 years, even with me wearing them just about every day. My “cheap” shoes never lasted that long! I still buy cheap shoes for other purposes like dress shoes and such, but I have come to appreciate that expensive, higher-end shoes are worth every penny!
    I really like Keen’s line of footwear — they are not a company I was familiar with. My faves are either the Charleston Lace in pinecone, or the Presidio in pinecone.
    What a fun give-a-way! 🙂

  496. Amy N says:

    The Portola shoes are really cute and look great for the running around “mommy uniform” I find myself sporting most days.

  497. Rebekah says:

    How cute are those winthrop boots?!?
    And about KEENS…my five your old son was the lucky recipient of a pair of hand-me-down keen shoes from his two cousins, meaning said shoes had gone through TWO five your old boys before they got to him. These things look BRAND spanking NEW!! No joke. Now, I shop the kind of thrift where I prefer to be given things rather than even buying them even second hand.
    But now if I or anyone else in my family needs shoes I’m definitely going to be shelling out the money for Keens. Comfortable, great looking shoes that LAST!

  498. Yvette says:

    I love the Venice H2. Living in SW Florida these would be perfect. Finally a sandle with support! :o) Thanks for hosting this giveaway.

  499. DJHinMO says:

    I do not skimp on shoes. I am a nurse, so I figure if I am gonna be on my feet for a few years, I better take care of them. Asics gels are my all time fav!

  500. Laura says:

    I love the Winthrop boots! I have not splurged on a pair of boots since college (20 yrs. ago), which should tell you what my shoe philosophy is….very cheap!!

  501. jessica says:

    calistoga in seal brown.. so cute! And my shoe buying philosophy, well… if they are trendy, then I buy cheap. If they are tennis shoes, then I buy quality. What a great giveaway!

  502. Redneck Diva says:

    I’m totally thinking I would rock the Palermo Mary Janes!
    My shoe-buying philosophy is this: As long as they are comfortable I can justify the expense, but cheaper is always better! My sister pays exorbitant amounts of money on shoes that are adorable and trendy but kill her feet. Not me – life is too long to wear uncomfortable shoes.

  503. Amanda says:

    my shoe philosophy: if they’re cheap and cute, they’re mine. 🙂 and i mean like, 4 dollars payless shoes cheap… BUT my daily shoes, i have a winter pair, summer pair, and a black dressy-or-jeans cute pair, were more expensive. i go for arto red etnies, mens skate shoes. amazing support and they fit great! for my black shoes, gbx brand, they also have great support, and my summer slip ons are reeboks.
    at keen footwear, the women’s blvd timberlines in beet red=amazing! i think that’s my dream shoe right there!!!!!

  504. Vanessa says:

    I don’t buy shoes very often so when I do I like to get something good that will last me a while. I figure if my shoes are going to last me 4 years I can justify spending $70 to $100 on them. Of course if I happen to find something cute at Target or Payless thats always nice!
    I would LOVE the Wear around MJ in Port Royale. I can see myself wearing them already…

  505. Rainy @ More Gravy says:

    I’m usually pretty cheap about shoes. I started seeing a physical therapist for ankles, knees and hips last month and she’s already recommended a shoe store to me! My favorites are the winthrop boots (or winthrop slip-ons, if boots aren’t included in the contest). I also love how you can sort shoes by size on the website. I usually have trouble finding size 11 shoes for my huge feet.

  506. Kim says:

    I like a lot of them, but I’ll go with Palermo MJ. I have always bought cheap shoes as well but was interested in your knee comments b/c I’ve had bad knees since college….

  507. sondra says:

    Put me down for drooling over the Palermo MJ’s, size nine, black! Keep Brad Pitt give me comfy shoes anyday!
    If you try these shoes, please comment on the comfort they do or do not bring.

  508. Marjie says:

    The Chamonix – totally impractical color (the green ones) – but for some reason I love them! I’m a cheap shoe shopper – if I spend more thean $25, I go into sticker shock!

  509. faith marandola says:

    Calistoga in blue….I have a guilt complex when it comes to buying shoes. I feel justified buying everyone else nice shoes, I can pick out nice ones for me. But, there always seems to be so many other things that we need aside from a nice pair of shoes for mom…. : ( ……santa, my feet hurt too!

  510. Kristan says:

    I think I would pick the Charleston Mary Jane in pinecone or Palermo MJ! I need to have something with a back or they always fall off. LOL
    I’m one to spend some money on shoes, even though right now we have no money. (So I guess I’m also not buying shoes!) I’ve found that spending the extra money up front for a seriously comfy shoe also means that they last a really long time. I’ve been wearing my birks for over 5 years now, my merrell’s for over 7. I see my husband go through shoes like nobody’s business and it drives me crazy!

  511. Sarah says:

    Oooh, so hard to pick–I love these! I keep looking at the Charleston Mary Janes in black. I’ve never paid much for shoes, but its nice to have a couple of good pairs.

  512. Jenni says:

    So hard to choose-but would probably go for one of the Palermo styles. At 37, I have had 4 foot surgeries and I have long,narrow hard to fit feet-so I spend good money for my shoes (whether I want to or not 🙂

  513. judy says:

    I would be happy with any of the Keen boots or shoes but I really think the Syndney II is kindof my style!
    I wish they were a little cheaper and I would buy several pairs of them!!

  514. Kerry says:

    Charleston Mary Janes!!!!!!!!!!
    I actually used to be like you are. I would wear anything from payless no matter how cheap.
    But then I got heel spurs. So I took the recommendation of a friend and got a pair of dansko clogs. I have worn dansko clogs just anbout everyday since I put my first pair on. They do wonders for my heel and are worth the extra.
    I have heard great things about keens I would LOVE to try them! Pick me, pick me, pick me!!!!!!!!!!

  515. SoCalLynn says:

    I had to start buying better quality shoes when I had plantar fasciitis. I still cringe every time I have to buy shoes and usually skimp.
    I love the Portola shoe, and I’d wear the Shitake color. These look very comfortable.

  516. Amy says:

    I think I’d go with the same ones you like and posted here. I’ve always cheaped out with shoes; mostly I just hate shoe shopping. By the time you find that cute shoe in a size 10, it’s not really all that cute anymore. Just huge. I did splurge on some Chacos last summer after hearing all the time how great they were…and ended up hating them. So that didn’t encourage me in the philosophy of spending big bucks on shoes. Sure would like to win a pair though!

  517. Mary B says:

    I really like the winthrop boots. And I do believe, as I get older, it is worth it to save for better shoes. The only problem is its been a long time since I have seen a new pair of shoes 🙂

  518. MaryBeth @ FourSillySisters says:

    Palermo MJs in Coffee Bean color would be my pick. I am a pretty picky, one of each kind of necessary shoe type kind of gals, who seldom ever shops for myself anymore… I’ve got 4 growing girls to keep in shoes and clothes!

  519. ja gililland says:

    Keen are the best wearing for my grandkids. They love them and I love the price and fit. The Targhee is my choice for them. I hope I spelled that right…..

  520. Jennifer C says:

    I like the Palermo boots or MJs. I usually go with inexpensive shoes and see what I can find on the clearance aisle. I would love to win these because I need some new brown casual shoes and don’t currently have the funding to get some.

  521. Laura says:

    I can’t get the page to load.. says it’s under construction or something! But, I have to agree, those clogs/mary janes are too cute!

  522. Jessyca says:

    I LOVE Keens! I have several pair that I’ve picked up at really good prices over the past few years. Marshalls tends to have them pretty cheap. I love the new Winthrop styles and would love the boot, but am guessing it wouldn’t fit right, so I’d pick the Winthrop clog.

  523. Ewokgirl says:

    I like the Calistoga.
    I do not believe in being frugal with shoes. Smart, yes, but buying cheap? No way! I’m a HUGE fan of Birkenstocks, and I have 7 pairs. Even my house shoes are Birks! I’ve been able to save money on them by buying on Ebay. Many sellers have brand-new Birks.
    I also have the problem of a small, narrow foot. No normal store carries my size, so dress shoes can be a nightmare to find. I’ve been fortunate that the Talbot’s Outlet in my town sometimes carries my size. I’ve bought some great dress shoes that actually fit my little feet for very little. But truthfully, if I had to spend $100+ for well-fitting shoes, I would.

  524. Debbie says:

    I would pick the Barcelona MJ’s. As I get older I find myself paying more for shoes. I just want my feet to be comfortable and not kill me.

  525. Jen says:

    My footwear philosophy? The cheaper the shoes, the more of them you can own!
    I love them all, but would probably pick Portola

  526. Michelle Meyer says:

    Ohhhh the Winthrop Clog in brown is what I would like!!
    And my shoe-buying philosophy is very much to spend money on good shoes. It saves you financially in the long run (and medically…)

  527. Julie R. says:

    I would probably go with the Betty Boots.
    Though they wouldn’t be to practical at the hospital.
    I usually buy a good walking shoe since I walk the halls at my daughter’s hospital a lot 🙂

  528. Martha says:

    Well, I am past that age where your feet start to give you problems. About 10 yrs. ago I ended up with feet problems. A trip to the orthopedic dr. and he told me the white canvas, no support no cushion shoes I was wearing were the problem. He told me to get a good pair of running shoes and wear them all the time. That is what I do. But I would love to find a casual shoe with some support and cushion that I could wear. I would pick the Charleston Mary Janes.

  529. Traci Best says:

    I’m with you on the Berkeley! I LOVE THOSE! I am definately a middle of the road shoe purchaser…I’m a plus size girl with a family history of arthritis, so I’m trying to protect my joints as much as possible.
    I’ll take those brown Berkeley’s in a 10 please! LOL 🙂

  530. Headless Mom says:

    I guess I’d try the Saratoga II. I desperately need some winter shoes that are comfortable but can’t find anything that is also cute. *sigh* I’m pretty picky and everything in the stores is ugly or too fancy.

  531. Jamie says:

    I love the Palermo boots… Hubs thinks they are hot. 🙂
    I have keens & my husband has a couple pair. We adore them. I buy shoes that are cute, comfy comes second. 🙂

  532. Laura says:

    As the owner of some BAD feet, I have to pay good money for shoes. I just got my first pair of Keens last summer and I love them. I like the Berkeleys. (And all the others;)

  533. Jill says:

    I would get the Vail snow boots. We just moved to Colorado after 10 years in Phoenix and last nights’ 5 inches of snow leaves me drastically unprepared!! LOL
    I am a huge fan of buying very good shoes that last. I spent $100 on a great pair of Dansko clogs in 2000 that I have worn atleast twice weekly since then. And they’ve held up great! I buy about 1 pair of shoes a year. I think you get what you pay for!

  534. Heather C. says:

    Sydney II would be my choice!!
    Honestly I gave up buying cheap shoes a few years back because for one, cheap shoes don’t last very long and they are notorious for giving me blisters! So I would rather spend the extra money on a nice pair and know they will be comfortable and last a long time!

  535. Ariane Carpenter says:

    Wow! What a deal! I would love to have the Berkley shoes in black in a 7.5. I think buying shoes that are expensive is hard when you are a mom, and generally mom’s aren’t the priority in buying things. Especially, expensive shoes. I would agree, I have had a good pair of shoes a time or two, and think they do make a difference in how they make your legs, hips, and feet feel. How exciting for KEEN shoe giveaway!
    Ariane carpenter

  536. Robin says:

    I want the exact pair you posted! I think they are adorable…sort of. See…I want them for my sister. Her two favorite qualities in a shoe are slip on and mary jane. So those two combined are probably ideal to her. With 6 fabulous kiddos to have fun with, I think she would LOVE these shoes and she more than deserves them. So I hope to win these for her.
    As for my philosophy…I don’t really shop a lot for shoes and if I own a pricey pair, my mom probably bought them for me. I am small and have small feet (girls size 2.5 or 3 is good) so when you can’t buy adult sized shoes, it’s just not much fun.

  537. MrsNehemiah says:

    I like the palermo in coffee bean.
    at $140 they’re almost 10 times what I normaly spend on shoes.
    but my DH has several pair of work boots at $200 a pair he believes in buying good shoes.
    Mrs N

  538. Coralie says:

    I used to have the same philosophy, until my sister’s doctor told her that her joint and foot pain had nothing to do with her having carried four children, but with her shoes. He “prescribed” her good shoes to wear in the house every time she was on her feet, (he recommended Birkenstock slides) and good shoes to wear out and about. Within months her pain was GONE.
    I’m now in the market. I think the Charleston Clog might be just the ticket.

  539. Mel says:

    I’m pretty sure that I’m in love with the Wear Around MJs…. or those ballerina ones. They’re both really cute. But the ballerina ones don’t come in blue (tragic).
    My shoe-shopping strategy is neither frugal nor expensive except for running shoes, when I go for the best I can get for my feet. Other than that, it’s Converse on sale! And any cute shoes I try to get on sale, but if they just aren’t going to be on sale, it can be worth the price sometimes.

  540. Lesley says:

    I like the Shellrock Mid. I don’t spend a ton of money on shoes but I don’t go cheapo either – somewhere in the middle I guess.

  541. Lisa B says:

    I would love the Keen Market st Palermo. I also buy cheap shoes, from Walmart, Payless etc. The thing that is expensive about my “cheap” shoes is that I will buy them when I visit my parents in Canada, at walmart, the seem to fit well, then after a few weeks/months I go to wear them and they don’t fit, and it is to late to return them. One day I will learn. Thanks for this contest.

  542. Laura@heavenlyhomemakers says:

    Yeah, I’m normally a cheap shoe girl. But I found a pair of new Eddie Bauer shoes at a second hand store a few years ago that I wear non-stop because they’re so comfy!
    If I won a pair of these awesome Keen shoes…it would have to be the Ridgeline Rose and Olive shoes. LOVE them.

  543. karen says:

    And they have bags too! How cute. I like the boots. actually, I like the idea of anything comfortable on my feet right now. I “do” christian retail and my feet are not my friends at the moment. (they’re talking about taking off for a vacation. sigh.)

  544. Rhonda says:

    I LOVE the winthrop style! But there are several others that I like also-hard decision to make! I tried these one just last week and they are on my Christmas list now. They are wonderful. I will pay $$$ for shoes because they usually will last longer, either because I take better care of them or they are made better, I don’t know. Anyway, Thanks for this opportunity. Merry Christmas to you and your family.

  545. Ashleigh (Heart and Home) says:

    I buy cheap shoes, too. My mom’s a huge advocate of the “you get what you pay for” philosophy, but in my mind, why pay big bucks for shoes that are going to go out of style two years from now? But classic good quality shoes that I don’t have to pay for? Awesome. 🙂

  546. Susan says:

    I picked the PALERMO MJ in dark brown. I have feet issues. My feet love summer and sandals, but they don’t like closed shoes. I love my Keen sandals and decided to try some of their shoes. My feet LOVE them. I am a very frugal person, but I splerge on Keen shoes. My feet are so much happier! All I need is a brown pair and I will be set! So Pick me, Pick me!!

  547. Leslie says:

    Never heard of these before, but they look comfy… I need some quality shoes for my plantar fasciitis, that I try to deny, but rears its ugly and painful head every-so-often…
    I like the wintrop slip-ons and the presidio for daily use, not a huge MJ fan, think my size 10 feet just aren’t cute enough for those.

  548. Christy says:

    I love the winthrop slip-ons in black! I believe that if you spend a little more on your shoes and wear them a little longer…your body will thank you!

  549. Denise says:

    I really like the PALERMO MJ. It is a shoe that I could wear for all occasions, that is very appealing to me.
    I currently live in my Berks, but Tennessee winters get a bit cold for sandals.
    I hate shoe shopping, so my philosophy waffles between the cheapest shoes that I can find (croc knock offs) & buying an expensive pair every few years in hopes it will be perfect & last forever.

  550. Becca says:

    I would have such a hard time choosing! I think the Charleston MJ or the one you chose which I believe was the Seratoga. I buy pretty cheap, but every once in a while I will buy a good pair and wear them out.

  551. Nett says:

    Oh, I love KEENS!
    I think I’d have to get the Winthrop boots.
    I have their sandals and a mary jane style that I wear year round and absolutely adore!
    My philosophy? Well, I never felt like I could afford expensive shoes. But then again, I figured if I didn’t spend too much money on them, I could have more styles in my closet.
    Not any more. I wear either my running shoes, my keens, my teva sandals (summer) or my Fat Baby Ariat boots. That’s it, 90% of the time.
    I totally agree on the knees, hips and low back. I have lots of pain and popping in my knees if I don’t wear the right shoe. So, here’s my “close-to-40” philosophy: Life’s too short to wear uncomfortable shoes!

  552. Gail says:

    I try to be frugal with my shoe shopping but after having some tendon problems, I’m willing to shell out more for good shoes!
    I love the Sienna and Palermo MJ shoes and am also digging the twenty six computer bag…might be an idea for Christmas!

  553. Amy says:

    I think I would get the exact same Mary Jane’s as you . . . or maybe the Charlston Lace in Seal Brown or Rum Raisin. I really hope it is a decision I have to make!

  554. Julie says:

    Ooooh, definitely the Palermo MJs. I’m with you…Mary Janes are always in style, and I really like that there are no buckles…just slip your feet in and go. My husband bought me my first pair of Keens this summer for my anniversary. The first time I hiked McAfee’s Knob I knew I had a winner. Pure comfort! Great shoes! Great giveaway!

  555. pam says:

    I like the Charleston in brown or the Berkeley that you have shown. I wear clogs a good bit, so those might be a great addition . Thanks so much for hosting the giveaway, Shannon.

  556. Melissa says:

    Wow! I LOVE the Sienna Ballerina and the black Winthrop Boot (though with my wide calves, I’d probably have to go with flats instead of the boots… curse you, wide calves!)
    Also, since I’m on my feet all day as a teacher, and have a few pairs of shoes that I have spent money on (that would be like $40-$80) because they have good arch supports and don’t make me feel awful by the end of the day. But most of my shoes that are not school-worthy are super cheap! (so all but three pairs that I own)

  557. Moleta King says:

    I’ve just had knee surgery. It’s not been fun. I’ve always just bought inexpensive shoes. I think I’m paying for that now. I like the Charleston Mary Jane shoes. If I don’t win your give-away, I may just drive to Dillards Dept. Store next week and buy myself a pair. Merry Christmas to my feet and knees.

  558. Tamra says:

    I absolutely agree with you 100%. I feel the same way about shoes, but as I get closer to 40 comfort rules. I love the shoes that you have pictured. I went to KEEN’s site and saw several that I liked, but what you picked I would also have to agree.

  559. Thea @ I'm a Drama Mama says:

    I love the Chamonix. Pretty cool.
    It’s funny that you should ask about my shoe buying philosophy. I’m pretty much a big ol’ cheapo. I hate spending money on myself. I especially hate spending money on shoes. I have big feet and narrow heels and finding shoes that fit well is a near impossibility. So when I find a shoe that fits, I wear it into the ground.
    But the more my back and legs ache, the more I realize that good shoes might be a good investment. I actually spent an hour online today investigating good walking shoes. Hopefully the price will be worth it.

  560. cmomgo says:

    I love the wear around MJ. My philosophy is to have a shoe fit perfectly, or not wear it. Sometimes it means I have to pay more. I also chose to spend more and have less.

  561. Joy @ Five J's says:

    Oh, I’m loving the Barcelona MJ (in black!). I don’t think I’ve ever spent more than $30 for a pair of shoes, and that was even for a pair of Nike’s from an Outlet store!

  562. Erin Goodman says:

    I’m wearing my Keens right now (a summer sandal from a few years back, with socks). That’s my shoe style. I buy good shoes VERY occasionally and wear them for *years*!!!
    I like the Calistoga MJ. Not sure which color…maybe blue???

  563. Meghan W. says:

    I have a love for good quality shoes. Prior to becoming a stay at home mom I sold shoes. I worked at children’s shoe boutiques and at department stores in women’s shoes. I appreciate what goes into a good pair of shoes and feel like the price is worth it.
    I love the wear around MJ. I think I’ll add them to my Christmas list.

  564. Jane says:

    Looking at the site, I think I’d be a Winthrop girl, either the slip ons, clogs or those gorgeous boots that would be wonderful in this cold, yicky weather. I’ve never been one to spend money on shoes, but after reading an ARC of Adrianna Trigianni’s forthcoming book, I desperately want to try a good pair of Italian leather shoes, preferably made by one of the characters in the book!

  565. Julie says:

    I tend to splurge on shoes, but living in the desert the past 3 years, I wear flip flops 9 months of the year.
    I like the Palermo MJ’s, too.

  566. Robin says:

    I’d pick the Winthrup Clog in black.
    I buy quality shoes and expect them to last a long time. I’ve had some Birkenstocks forever. They are still comfortable and look decent.
    Nothing like well made shoes.

  567. Rachel says:

    What a great giveaway! I love the Calistoga’s in Seal Brown.
    I’m a bargain hunter when it comes to anything, but for shoes I am willing to pay a little more. I get a lot of shoes at TJ Maxx and Nine West Outlet. I also like Sketchers and Bear Paws. Not too expensive, especially when you hit up the the BOGO at Famous Footwear!