The Hunt: Stylish Comfort Heels

comfortable heels for workSure, we all know what basics professional women are supposed to have in their closets, but if you’re buying one for the first time or replacing one you’ve worn into the ground, it can be a pain to find exactly the right incarnation in stores. In “The Hunt,” we search the stores for a basic item that every woman should have.

One of our top pages of all time is our regularly updated Guide to Comfortable Heels — and while that guide includes brands outside of those that bill themselves as “comfort” brands, sometimes you just really want a heel that is built like a sneaker, whether for commuting, for long days on your feet, or for general foot problems.  Finding stylish “comfort” heels can be a challenge, though, so I thought we’d round some up.

Some of the Hall of Famers are pictured below:


Pictured, top row: one / two / three

Pictured, bottom row: four / five / six

Some of our favorites for today include:

comfort heels under $100 Aerosoles are known for having affordable comfortable shoes, and these 3″ heels have 24 5-star reviews over at Zappos.  They incorporate Heel Rest, a “technology designed to distribute your body weight toward your heel, and away from the ball of your foot.”  They’re available in four colors in sizes 5-12 in regular and wide sizes. Another highly rated shoe from this brand: the Domino dress pump — sold out in all colors except navy at Zappos, but Amazon still has it in black and red for $46-$77. Pictured, for $79:  Aerosoles Dolled Up
stylish comfort heelsWe’ve featured this shoe a ton over the years (and it’s got a zillion great reviews on both Nordstrom and Zappos), but I’ve never noticed it in any colors but the neutral ones — I’m excited to say it now comes in NINE colors over at Nordstrom, all for $98. Corso Como Del
comfort heels for workEven though this platform is higher than what I usually recommend for work (they’re .75″ and I usually recommend no higher than .5″), I think these shoes look great for work.  They use a Cushion Plus™ technology to ensure “feet are comfy withe very step,” and though they only have 3 reviews, they’re all five stars. They’re available in black suede and patent, as well as this lovely plum suede, for $110 at Zappos. (These are from Clarks’ Narrative Collection; note that lots of ladies have also loved the Artisan collection over the years — if you have a strong preference for Artisan you may want to check out these pumps.) Pictured: Clarks Kendra Sienna
comfortable heels for workOK. I didn’t intend to feature quite so many purple pumps today, but I’m excited about these heels too: the Rockport Total Motion pump has been around for years and is highly rated over at Nordstrom — and now it comes in this lovely burgundy snake print leather (also in a black snake print as well as a ton of solid neutral colors). The shoe is $119-$128 at Nordstrom and Zappos.  Rockport Total Motion Pointy Toe Pump 
comfort heels cole haanWe’ve drooled over these Cole Haan pumps before, but it’s nice to see the ten solid reviews they have over at Nordstrom. Even better: they’re on sale! The shoes were $250, but are now marked to $159. (Amazon has more colors, some sizes and colors marked as low as $103.) Cole Haan ‘Highline’ Half d’Orsay Pump
minimalist comfort heelsI originally dismissed Eileen Fisher shoes as just another licensed brand name, but their shoes are worth noting if you’re looking for comfortable, minimalist styles. I like these architectural block pumps, which feel really modern.  They’re available in black and gray for $210. (Another modern heel in this price range: these well-reviewed pumps from Paul Green.) Pictured: Eileen Fisher ‘Hawk’ Block Heel Pump

Ladies, when you’re looking for a comfort heel, where do you start the search? Have you bought any amazing, comfortable, stylish heels lately? 


Like this feature? Check out other recent installments!


Stylish Comfort Heels For Work


  1. I’ve found JCrew’s heels to be fairly comfortable for the height, and they currently have a range of heights trickling in for the fall — the Dulci (kitten) and Elsie (medium high) are my two favorites.

    That said, I feel like you need to try on a bunch of different brands and sizes. It’s like bra shopping. One person’s OMG Swear By It shoe can be painful on others — feet are all shaped so differently. Like for me, Cole Haan’s ankle-to-ball of foot distance is always too short for me (I guess I have short toes relative to my foot length?!), meaning the extra room at the ball is in the wrong place, and Talbot’s cuts their toes too narrow (which is why I can wear their sandals but not closed toe shoes). Other brands might have a too-deep or too-shallow heel cup. Etc etc.

  2. I love the look of the Corso Como heels but have to remind myself that the back of my feet slips out of their shoes and these would be perilous, to say the least.

    To add a brand I don’t often see mentioned: boden. I got their 3 inch (3.5?) pumps last year and was pleasantly surprised by how wearable they are. Not pretending I could walk for miles in them, but totally good for all day wear in the office.

  3. Online Dating Profile :

    I recently ended a long term relationship and am finally ready to date again. I want to try online dating, but the problem is that I don’t really have any recent pictures of me without my former SO and I gained a fair bit of weight during the breakup so the older ones I do have aren’t reflective of my current body. How do I go about getting pictures and do you ladies have any suggestions for ones to include? What types of photos do you usually include in profiles?

    • Do you have a camera? Can you just set it with the timer? Or can you have a friend take a few with either a regular camera or a phone? I think it is best to include pictures where you look like you are doing things you enjoy–so if you like outdoorsy things, take a picture outside by a tree or something (ideally, it would be a picture doing an activity you like, so hiking or whatever, but in the meantime you could do something easier just to get a photo up.)

    • Anonymous :

      How important is a picture? Do people assume the worst if there isn’t one?

      For my one foray, I was overwhelmed (and didn’t have a picture up, but had one that was sendable) with responses. I didn’t want more, but maybe I was getting people expecting someone to be non-photographable or a liar about size (which I usually ticked the box for fit or trim or something vague but 100% true). I was really mortified about people from work digging me up and for that reason wouldn’t feel very comfortable with that (just get over it? the yield still be more what you want?).

      • BabyAssociate :

        I’d say that a picture is an absolute must. I believe a lot of sites actually let you filter people out who don’t have photos.

        There’s no shame in being on an online dating site! Everyone does it, I’m not worried about my coworkers finding out I have a profile.

      • Anonymous :

        You cannot online date and meet real people without a picture. The only people that will be interested without one are undesirable people who are trolling for any warm body or trying to scam you. Online dating is normal now, everyone does it and you shouldn’t be worried about your coworkers.

      • Anonymous :

        A picture is an absolute must. Don’t bother if you don’t have one.

    • Veronica Mars :

      Grab a close friend and have them take some good pictures of you outside, inside, doing your favorite hobby, etc. Super easy and doable in an evening. Do a variety with some different outfits. Should only take an hour or so.

      • This. And grab an honest friend, who will tell you how to pose or capture candid pictures of you.

    • At a minimum, you need a pic of your face and a full body shot.

      I had a friend come over and take some closeup pictures inside, and some full body pics outside. I had the dog on a leash with me in the full body shot so that it looked more “natural,” and not as posed.

      The secret to taking good pictures is to take a LOT. Out of the many will come the few that you will like.

  4. I like Payless Karmen and LK Bennett Sledge.

  5. Does anyone have experience with the quality difference in Cole Haan vs Cole Haan Outlet? I’m looking at their 65mm pump and they offer an almost identical product at each. One is the Hellen Grand (outlet $180) and the other is the Grace Grand (retail $270). I’ve tried on the outlet version and liked the fit/style. However, I’m pretty rough on my shoes so I wouldn’t mind paying more for something that will last. I will post links in the reply.


    • I have been wearing the outlet Elsie version of the Talia flats, and the talia flats themselves, and honestly, I much prefer the elsie ones. The shape seems different- they are a little bit shorter in the toe box and the heel doesnt come up quite as high in the back- but I havent seen a noticeable difference in quality.

    • I’ve had pretty good luck with outlet flats and wedges. I had a pair of outlet heels where the shank broke away from the heel under normal use. That was frustrating for shoes that cost $150+

  6. Anonymous :

    I am extremely anti-heels but I sucked it up and bought a pair of black Nine West pumps for a job interview and they were surprisingly not terrible! I could actually walk! Not sure of the exact model name but the heel wasn’t too high.

    My Cole Haan wedges (back when they were partnering with Nike, RIP) are the most comfortable pair of dressy shoes I own.

  7. A little while ago, I saw a man walking on the side of the freeway as I was driving home at rush hour. I thought about calling 911, but I figured the guy must have run out of gas or something and I didn’t want to create more of a hassle for him. The next day, I read in the local news that a pedestrian was killed on the freeway near where I passed the man. I feel so horrible for not reporting this. Maybe if I’d called, the police would’ve been able to save his life. I will definitely be more diligent about reporting things in the future, but I have to know, what would you ladies do in that situation? Was I as awful as I feel for not reporting it?

    • Wildkitten :

      I saw on a man walking along the freeway yesterday and didn’t call it in. I figured he was walking to an on/off ramp because of car trouble.

    • full of ideas :

      Nothing you can do now, but moving forward, make the call because you never know. But don’t beat yourself up over it

  8. So glad you listed the Rockport Total Motion! I think I’ve included them in responses to comments before. I love them. I just recently bought them in a whole bunch more colors. Also, I have a slightly wide foot so I love that they come in wide widths.

  9. Also, has anyone with slightly wide feet bought the Ferragamo Vera or Verina? How did they fit? Are they comfortable? I’ve heard mixed reviews but they’re so pretty!!

    • anon prof :

      I have the Vara in wide. It’s a lovely shoe, but the leather is incredibly stiff. They are not great shoes if you have high arches.

  10. I second Naturalizer-any shoe with the “N5 technology” is really comfy and wearable all day. And I have a very high standard for comfortable shoes (my knees hurt now after wearing heels, aging is so fun…)

    Also, I bought a pair of Ivanka Trump heels, and I was shocked how wearable they are. You’ll probably be ready to take them off at the end of a long day, but they’re not uncomfortable, and they’re never painful. They also hold their nice shape well.

  11. I am a shoe snob but I am also very frugal. I want nice Italian leather shoes but I would rather pay my mortgage with $600. The perfect solution is Ferregamo on eBay. They run true to size and I have never had a problem.

    I have also been able to find them for about $12 in consignment stores here. Apparently, few women in this area know the brand, so even the nice consignment stores can’t price them too high. (In contrast, I had to pay $45 for cherry-red Doc Martens at a consignment store. Which, really, seems about right for this place. :) )

Add a Comment

Thank you for commenting. On the off chance that your comment goes to moderation, note that a moderation message will only appear if you enter an email address. If you have any questions please check out our commenting policy.

work fashion blog press mentions