The Quest for Comfortable Heels

The Quest for Comfortable Heels | CorporetteUpdate: Check out our new and revised guide to comfortable heels! And if you’re new here (welcome!), please consider subscribing to our email newsletter or checking out our Top Posts!

Today’s reader mail has to do with comfortable shoes…

I was wondering whether you had heard of Tsubo shoes. I recently posted on Facebook about my quest for comfortable heels, and instead of the usual “get the Cole Haan Nike Air pumps” suggestion, two people posted about Tsubos. I checked out the site, and the shoes really do appear to be very well made and at $100 to $150, a reasonable expenditure, even for me. Thought it might be worth a post. Many of your readers certainly must be walking to the courthouse regularly, and are probably looking for fashionable yet professional footwear that won’t cause them to limp by the end of the day.

Seriously, forget the Holy Grail — this is one of our lifelong quests. As one might expect from all the Mary Jane and other comfortable-type shoes we post (what? we wear ’em with pants) this author has problem feet — it’s incredibly difficult to get shoes that both feel and look great.  Not only does it seem like there are variances within each brand (e.g., some of our Cole Haans we love, others we want to throw across the room), but shoes that were favorites in previous seasons become hated things in newer ones (and never get better). Whine, whine — perhaps we just need a higher tolerance for pain.  (As for the blog, we can’t bring ourselves to recommend, sight unseen, shoes that we would never even order ourselves.  So again, ladies, send us your suggestions!)  In terms of pain, we actually read a book about feet a while ago that contained some helpful exercises, such as drawing the alphabet with a pointed toe, or spending a few minutes, barefoot, trying to pick up a pencil with your toes — but that doesn’t help with the comfort of shoes to begin with.

Regarding Tsubo: heard of them, but have never owned a pair — one of the pairs we considered buying on Zappos several months ago seemed to have a number of comments about the leather stretching.  But that doesn’t mean we’d never try the brand in general.  (Pictured above: Tsubo – Amset, on sale at Zappos for $114 (were $130), available in sizes 6-11.)  The brands we’ve heard most often touted as comfortable ones can be broken down into these sorts of categories:

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  • Designed by master craftsmen, incredibly comfy, but incredibly pricey:  the usual suspects:  Manolo, Louboutin, Choo(we’ve read that the Manolo team thinks 3″ is the highest heel a woman can comfortably walk on, whereas the 4″ Louboutins are worn by all the celebrities because the stacked platform makes them very comfortable)
  • Designed for comfort and mid-range pricey ($250-$500):  Cole Haan Air, Taryn Rose (the brand is designed by a podiatrist!)
  • Funky or clunky, depending on your taste, but comfortable investments:  John Fluevog, Frye, Born, Sacco
  • Lower-cost comfortable (but also often clunky):  Clarks, Beautifeel, Sofft, Geox, Peter Kaiser, Sudini (we’d put Tsubos in this list)
  • Mall stores that bring trendier shoes to you at a more reasonable price: Aerosoles, Naturalizer, Rockport

With that said, we still find that luck — not research — nets us our most comfortable pairs of shoes.  In fact, our favorite 3 pairs of shoes right now are from the following brands:

  • Clarks — a simple pair of black boots (the “Luna Reef”) for wear with pants — comfy,walkable
  • Sacco – black leather and suede pair of 3″ pumps that we keep at the office (got several seasons ago)
  • Naturalizer — a wee bit embarrassing, but we have a pair of pointy-toed kitten heels from years ago that we can walk for miles in.  The sole is actually wearing out on these babies (in a non-replaceable way), so we desperately need to find a new “I’m wearing a suit, standing for 3 hours, and then walking a mile” pair of shoes.

But perhaps we just need a better breaking-in procedure — a friend told us that the trick was to wear the shoe barefoot and then saturate the leather with perfume — something about the alcohol shrinking the leather to your foot.  We’ve never tried this (and actually, if memory serves, one of the main points to the book was that there is no such thing as “breaking in” shoes; they either fit or don’t).

What are your favorite three pairs of shoes right now (if possible, post links!)?  Which brands are your go-to ones for comfort?  Do you do anything to break in your shoes?


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  1. I thought that I would forever be barred from wearing heals until a 30-year veteran shoe salesman tipped me off on the problem. I needed a wide width. He sent me to a shoe store that specializes in hard to fit feet, and I bought shoes that are actually comfortable and not terrible to look at. I can also search Endless for my width and find some decent shoes, but they have to have heel straps since ankle is not wide.

    • Anonymous :

      Can’t believe no one mentioned AGL flats or Naots. Love them! Love aquatalia boots as well. Very comfy!

  2. newassociate :

    add stuart weitzman to the top category. i have a pair of red patent “muse” heels that are much more comfortable than the cole haan carma almond toes which i always want to chuck across the room. the cole haan carmas with the snipped toe are *great,* but the almond ones… argh! the black calf “muse” are still sitting new in their box… they didn’t feel as instantly comfortable as the red ones, so they may unfortunately be going back unless i can find them at nordstrom.

    i keep thinking about getting the louboutin “simple” 3.25″ heels but i’m concerned that the (im)famous red sole will say things about me that i don’t want (unprofessional woman, spends too much on shopping, doesn’t take work seriously and just wants to shop, and other baseless stereotypes)

    does anyone have louboutins? have you received any negative feedback or comments regarding them?

    • The most comfortable pair of heels I’ve ever had was a pair of Ferragamo 3″ heels I randomly bought on sale at Saks years ago. I have them to this day, and if I ever need to do a lot standing/walking while wearing heels, they’re my go to shoe. I dread the day I will finally have to get rid of them.
      (For those w/”problem” feet — if you’re pay full price at their store, they will stretch them for you in certain instances)

      The worst shoes (as in, I could not even wear them to and from a cab) were Michael Kros chunky heels.

      I have had mixed experiences with Naturalizer. One of the most comfortable pair of boots I’ve had (2 inch heel) came from there, as did one of the most uncomfortable (4 inch).

      I’ve heard mixed things about Taryn Rose. Despite the comfort claims & the chunky appearance, I have heard gripes about some of the particular models.

      I would also add Ellen Tracy shoes to the lower cost, comfy list. Only caveat is that ET shoes seem to be changing in style lately — not sure how that affects the comfort of the brand overall.

      The one nice thing about the less-than-comfy shoes I’ve amassed over the years is that they stay in remarkably great condition (since I wear them so sparinglly). Always look on the bright side. . . .

      • Concur on Ferragamos. So comfortable that I keep them far beyond their natural lifespan. Also Stuart Weitzman.

        I too have heard that Taryn Rose is faking the funk. I too love my Naturalizers when I REALLY have to walk a mile. And I am now looking for shoes that are comfortable but cool. And am also considering Tsubos. I sense a trend.

        • One more vote for Ferragamo. The styles are classic (not boring though) and conservative even for the court-room (I love the Ribes style – comes in closed toe and peep toe in a variety of colours). I have flat, thin & wide feet , size 9 with abnormally long toes. This has made it virtually impossible to find shoes where I live (avg shoe size seems to be 5/6 here!!). The heels usually are not over 2.5/3″ and super comfy all day. I will never try another brand for work now – IMO, better to have fewer pairs that I love, rather than a lot that I want to throw across the room! 2010 is the first year that I don’t have to look for shoes thanks to my so-worth-it 2009 purchases!!

      • Also singing Ferragamo praises. Just got my first pair – 3″ heels – and can run up and down office hallways all day no problem. They are in the $4-500 range full price, but so far, definitely worth it.

        • newassociate :

          i went to ferragamo today and got a pair of heels called “nene.” i will blame all of you for my credit card bill :). the nene is apparently new for spring, and available for the first time in black calf. previously, it was only available in patent and was one of their best sellers. they don’t seem to be online anywhere yet, so i can’t share a pic. they are a very simple, round but just slightly almond toe, a good diameter 3″ heel without being chunky. no embelishments, no detailing, just simple.

          i always wear a 7, but the nenes are running a half size large. i could stick my finger in the back of the shoe wearing the 7s, so i got the 6 1/2s. i tried them on in the store by walking around and standing on the hard floor for ~15 minutes, and they seemed very, very stable. to give myself time to recover from the shock of buying shoes that are a) that expensive and b) at full price, they will be staying in the box for a while.

          i also picked up a pair of, which is a much nicer gray with much less green in it IRL. i took my normal 7 in these.

          i tried to try on the louboutin 70s at saks and neiman, but neither had 7s in stock. i think the ferragamos with the slightly thicker heel will be better for me anyway, but it would have been nice to try the louboutins.

          i cannot believe i just spent so much on two pairs of shoes. must now root around in my closet for new-with-tags items that i can return to help “balance” out today’s purchases. yikes.

    • I have the Louboutin simple heels and they are one of my favorite pairs. I was told 2 years ago that I should probably have foot surgery due to developing bunions – apparently a progressive problem. I blame the preceding 3 yrs of high pointy-toed heels, should have listened to my grandmother.

      Anyway, these are very very comfortable, classic, always look great. I got the lowest heel, the simple 70s, in a pale pink that is a nude for me. So handy. And after upgrading my shoe wardrobe (and throwing away the pointy toes), my feet don’t hurt anymore – no surgery.

      Oh! and here they are! This is the first time I’ve seen them for sale since this past Feb when I got them – guess it is a seasonal thing.

      I don’t think they “say” anything about me in particular. They are a pretty classic style. If anyone is that interested in the soles of my shoes then they probably are into shoes as well.

    • divaliscious11 :

      Yes, and no. All I’ve ever received are cute shoe compliments…

      • I love my simple 70s loubs, they are one of my very favorite pairs. Very comfortable, I can wear them all day. Don’t even automatically kick them off under the desk like almost all other heels. And, of course, their classic styling is beautiful. I have worn them so much, I feel like they’re a great deal! Not that I can fill my closet with them.

        Anyway – since upgrading my shoe wardrobe, I have much less foot pain (whereas I was told to get foot surgery a couple of years ago – due to the preceding years of high heels and pointy toes).

        Here’s the link to the 70s – pretty low heel. The color is a pale pink which works out to be a great nude for me – v useful.

        And no, I have gotten no negative feedback. The style is classic. If anyone is paying attention to the soles, good for them. Guess that means they are into shoes, too.

        oh – as to other favorites right now – mainly flats. I have some black patent Stuart Weitzman flats that I love, and actually got a pair of gray suede flats from Banana Republic in the mail recently and have been pleasantly surprised – lots of padding, pretty comfortable! Get lots of compliments on them. Sorry no link, guess they have sold out online already.

  3. I know that they were panned on the board a while back, but you can’t drag me away from my Chie Mihara’s. I’m surprised that you mentioned Fluevogs ( I can’t help but think about Madonna in her Truth or Dare movie).

    I have heard some good things about the comfort of BeautiFeel and Ecco shoes–they don’t particularly excite me, but YMMV.

  4. Not to generalize, but my experience has been that where a shoe is made really matters.

    My most comfortable shoes were all made in Italy. My most uncomfortable were all made in China. Incidentally, that’s also true in terms of how long the shoes lasted.

    I’m sure there are exceptions, but seeing where a shoe is made tells me what I can expect better than anything the shoe’s description says re: comfort & walkability.

    • That’s interesting – I’ll have to start paying more attention to that

    • I completely agree. As a rule, I don’t buy shoes made in China (except for flip flops and tennis shoes, perhaps). Quality is better with shoes made in Italy, Spain, and Brazil.

      • You can literally track the demise of Ann Taylor by the sourcing of their shoes … Italy, then Brazil, then China … down, down, down. Yet strangely their shoes are now priced higher than ever.

        • The outsourcing of ALL manufacturing to China actually really bothers me. Much of what’s sold at Brooks Brothers now is from China; and same for other so-called “upscale” or “luxury” brands. I understand that the quality coming out of China has gotten better, but I can’t be the only one bothered by spending upwards of $500 on a bag to see a “made in China” label discretely hidden inside. The quality really is worse than it used to be, and yet the prices are, if anything, more expensive. What gives??

          • Sorry if that was too off-topic, but just had to gripe as I am really at a loss. I don’t mind pay higher prices for non-disposible clothing that will last longer but almost everything at all price points has become “disposible” quality. What’s a girl who wants things to last to do? Buy cheaper stuff and just spend all my money on careful dry cleaning??

  5. I bought a pair of pumps (Vince Camuto) that were under 3″, and it changed my life. I wore them to a wedding, and was shocked at how much dancing I could do because my feet didn’t hurt. I’ve hustled to court in them just as fast as my male colleagues. I haven’t bought a pair of shoes that were 3″ (or higher) since. It’s incredible what a 1/2 inch difference makes.

    So, my advice: If you want comfort, buy whatever shoe you like, but nothing higher than 2 1/2″.

    • One more comment: For every day, I love the Tory Burch ballet flat.

      • I love my Tory flats, too – for looks and with socks. But, no support really (like most ballet flats) and the eleastic backing killed my heels this summer! Blister city.

    • I have very narrow feet to the point that I can’t wear high heeled sandals so to find any heels is a hunt. I was just browsing through Dillard’s and the two pairs that I couldn’t live without we’re the Jessica Simpsons pumps and the Reba “corrina” pumps. By far the most comfortable heels I own other than wedges.

  6. I have a relatively wide forefoot with a relatively narrow heel. I’ve had very good luck with Franco Sarto’s; they are reasonably comfortable and I can walk all day with them and only have a little bit of foot fatigue. The price point is right too, and they tend to follow major trends. They would be the only brand of shoes I would buy on-line; my foot is too finicky otherwise. I have a pair of cole haan heels that I don’t find that comfortable (oh, the disappointment) but I have a pair of black leather driving mocs that I adore. They are soft soft soft and totally comfortable. I wear them at my desk with pants if I’m not seeing anyone important. They’re like slippers!
    The rest of my life I spend in the operating room — if anyone wants an exhaustive, overly tedious and probably unhelpful diatribe on the pros and cons of various clogs for OR shoes, please let me know and I’d be happy to oblige…

  7. I’ve never found a go-to brand that is consistently comfortable. I have a pair of Tahari heels I could wear all day, but I bought another pair and they killed my feet. And I actually bought a pair of the Lela Rose for Payless heels and they turned out to be incredibly comfortable, although I don’t think they will last forever.

    One thing I will unhesitatingly recommend is Yoga Toes (or one of the drugstore ripoffs of them, such as I try to wear them a couple of times a week, and I have really noticed a difference.

  8. I have slightly wide feet, and a really high arch, so heels can be killer. In general, I love the way Kate Spade’s fit me, as well as Michael Kors, but these Calvin Klein’s are my ultimate go-to’s:

    Basic, classic, and super cushioned under the ball of the foot. I’m on my 2nd pair because I wear them constantly.

    • I’ll second this! I love these shoes – have them in both black and navy and I wear them all the time.

  9. I actually really love the Ann Taylor Perfect Leather Pump – very nice looking and basic, not too expensive, and quite comfortable. There is a sale currently on the Aubergine colored ones.

    I also have an extremely comfortable pair of Nanette Lepore Mary Jane style shoes and a pair of Kate Spade pumps that I adore.

    My most uncomfortable shoes are Coach and Michael Kors – they are very cute but KILL my feet!!

  10. Zappos has a couple of the Tsubo’s on sale, with free shipping (both ways) here:

    If anyone tries them, I’d love to know how they feel. I still have yet to find that perfect go-to heel for days requiring extra comfort!

  11. Ridiculously comfortable, affordable and fashionable. I have them in two colors!
    Calvin Klein Olive

    • I second these shoes. I have them in a sparkly brown, and they are incredibly comfortable. I usually can’t even wear a 3″ heel at all (stick to 2 or maybe 2 1/2″), but I like these so much that I’m thinking of adding more to my collection.

  12. Prada makes some comfy heels – they LAST, and can often be found on sale.

    I am on the fence about the Loubs at work – I REALLY want a pair of Louboutins, but a part of me laughs a little when I see women wearing them to court. It’s not an issue of the level of professionalism the shoe exudes, but rather, that I can think of 10 better places to wear a sexy/ sophisticated red-soled shoe. =)

    • divaliscious11 :

      Agreed on Prada… but they a few that hurt unless you are going to be a on bar stool/couch…

  13. I’ll add my chorus to the worst list — Michael Kors. I recently gave up and donated the most uncomfortable pair of chunky heels in history to good will. I probably should have just thown them away to avoid inflicting pain on another unsuspecting women. I’m pretty confused about how it is that I thought that I could walk in them in the store but now can’t even take a few steps in them.

    My most comfortable pair of heels is a pair of Gunmetal brand suede brown and gold peep toes, probably about 3″ heels. I think I bought them at Off Saks, and at the time (a couple years ago) the sale price seemed ridiculously high, but I now believe that they would have been worth it even at full price. I totally lucked into them because I had never even heard of the brand and they were an impulse buy.

    On a related note — I’m looking for an incredibly comfortable pair of heels for my wedding day in a deep red color. Open toe, closed toe, it doesn’t matter, as long as they are super comfortable and gorgeous. I’m willing to pay a good deal of money, but my budget is far from unlimited. (I’d consider a $500 shoe, but can’t do $800 Louboutins; would prefer something in the $200-300 range.) I have a few months to hunt the sale racks. If anyone has a specific suggestion, I’d greatly appreciate it!

  14. I highly recommend the Nurture brand at Dillards in the more budget conscious category (usually $80-90, but you can get them on sale for half that). I think the brand is designed specifically for Dillards. Some of the styles are frumpy, but others are classic and attractive– both heels and flats. The footbed is deeply padded. Even my mother and sister (both of whom will only wear comfortable shoes at the cost of fashion) like these shoes.

  15. GREAT topic! Nice reco’s all around. I have wide, big feet (8 1/2) for my stature. I swear by a) suede and/or b) peeptoes. If I can get both in the same shoe, more chances are my feet or comfy. IMHO, patent leather is very unforgiving, and the pointier the toe, the more chance for “grit-your-teeth-almost like childbirth-pain” after 2+ hours of wear.

  16. The only comfortable heels I have ever worn are the Sofft Carmas. (I have extreme problem feet — my right shoe has a 1-2A toe and I think a 4A heel due to an extra toe, my left foot is 3-4A all over but also narrower at the heel — it was not until I bought these shoes that I realized it was possible to wear heels without bleeding, and most styles are still right out for me. But these shoes still fill me with glee every time I wear them, and I’ve happily walked the 3/4 mile from my house to the subway and back in them.)

    • I have 2 pairs of Sofft shoes very similar to these (they have a little rosette where the button is) – one in chocolate suede, one in burgundy suede. SO comfortable. And look great. A really good buy!

      The Tory Burch flat that’s so common? I got it in gold, thinking it would be a fun shoe with jeans, but it’s really uncomfortable. The band doesn’t go high enough on the back of my heel, so I’m constantly walking out of them. And there is no support whatsoever (I have a high arch). Sadly, they’re relegated to looking-fab-at-the-beach-or-pool-but-no-actual-walking.

    • Thanks for the recommendation. I have a similar problem, 2A in the toe, but much, much narrower in the heel. I’ve yet to find a pair of shoes that fits really well. I may give the Sofft shoes a try.

      • Welcome! They only work because of the strap, but hey, that’s fine with me (and I get a lot of compliments on them, too). If you find anything else that works I’d love to hear.

        • I love Sofft too. I live near a Marshall’s shoe shop that sells the last season’s styles for $40, I’m in heaven.
          I also like Charles David.

  17. I don’t have a problem with feet and wear high heels daily. I even manage to keep up the fast stride of my 6’2″ husband (and I’m 5’4″ on a good day without shoes on)…that being said, the most comfortable shoes I’ve ever had have been nearly anything from the Linea Paolo line, the store brand of Nordstroms. I also find Franco Sarto (esp. the artisan line) very cushy and easy to wear, if slightly “clunky” looking.

    My heart aches for all the fashionistas out there with feet/shoe problems.

    I’ve got my own, but now is not the time to share body woes (or is it aging?).

    Hang in there gals; your above the knee style is wowing folks anyway.

  18. divaliscious11 :

    Most comfortable heels:

    1. I have a pair of Jimmy Choo slingback in neutral that are maybe 2.5″ high that are the most comfortable heels! So much so that I am on a quest for an a replacement pair, and additional colors in the same shoe….
    2. Stuart Weitzman – can wear all day

    I have Loubie’s and while they are comfortable, they are not wear all day comfortable like the above. Oh, and I almost always have a platform, even if its hidden. The above Choo’s don’t but they don’t need it.

    4″ heels – love them but can’t wear them anymore since kids…. have 2-3 pair still in my closet but if I find a good consignemnt shop, I am going to have to let them go…..

  19. I have problem feet too (wide, absolutely flat, and a bunion on one foot – probably from high heels in my youth!), and I’ve found that slingbacks seem to be more comfortable for some reason, almost regardless of the heel height. Also kitten heels (or spoon heels, as my mom calls them) work well for me, but they tend to be a lower height. I find Liz Claiborne and Sarto (as noted above) shoes generally comfortable. But maybe that’s because I haunt DSW, and they seem to carry those brands a lot!

  20. Hardly fashionable but oh-so-comfotable: Mephisto, Merrill, & Clarks.