Guide to Comfortable Heels

comfortable-heelsThis shopping guide for comfortable heels is inspired by one of our all-time top posts from 2010, The Quest for Comfortable Heels. We’ll try to revisit the text of this page from time to time; in the meantime please add your own comments about comfortable heels on this page. Please keep all comments on this page strictly on topic. Last updated: Jan. 23, 2015.

Forget the Holy Grail — the quest for comfortable heels can be a lifelong hunt for some women. As one might expect from all the Mary Jane and other comfortable-type shoes I post (what? I 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 my Cole Haans I love, others I want to throw across the room), but shoes that were favorites in previous seasons become hated things in newer ones (and never get better). Note that if you’re looking for shoes for interviewing, you can interview in flats — and in fact, any height be too high for interview heels if you can’t walk a few blocks in them.

Brands for Comfortable Heels: The brands of heels most often touted as comfortable ones can be broken down into these four price ranges (also see our post on tiers of shoes), and then into two categories: the first is the stylish/trendy brand that everyone swears by for comfort (whether it’s marketed as a “comfort shoe” or not). The second line is the ones that are marketed for comfort — but they’re often a bit funky/clunky next to, say, a pencil skirt.  For specific shoe recommendations other than those pictured above (both from Kat and the readers) check out our regular Hunt feature (hunting for one wardrobe basic in a range of prices) or our afternoon Coffee Breaks (which often feature shoes).

In our last poll on comfortable heels, readers mentioned other favorites including Alfani Step n’ Flex, Brooks Brothers, Butter, Calvin Klein, Coach, Corso Como, Enzo Angiolini, J.Crew, Joan & David Circa, Seychelles, VANELi, and Via Spiga. We’ve also named names for some of our least comfortable heels (brands and styles).  If you’re looking to upgrade your shoe collection in general, you may want to check out our discussion on the different tiers and levels that people consider for shoes.

Special Sizes:  Wide heels can be found; we’ve also talked about general shopping tips for problem feet.

Pictured below, a few of our (and readers’) perennial favorites:

  1. Michael Kors Flex Pump ($99)
  2. Stuart Weitzman Platswoon ($340)
  3. Kate Spade New York Karolina ($298)
  4. Calvin Klein Diema ($69)
  5. Christian Louboutin’s Simple Red Sole Pump ($675)
  6. Comfort Plus by Predictions Karmen Pump ($28!)

Alleviating Pain Caused by Shoes, During: I got the chance to try some Insolia inserts, and they really do make a difference for heels — something about the slim pieces of plastic helps my flat feet feel more comfortable in heels. (Read my Insolia review here.) I’ve also been a longtime fan of ball-of-the-feet inserts, like those by Dr. Scholl’s or Foot Petals.  Finally, if you really can’t walk far in your heels, there are a number of foldable ballet slippers that you can stash in your purse, including City Slips, Footzyfolds, and Dr. Scholl’s Fast Flats.

Alleviating Pain Caused by Shoes, After: The book Your Feet Don’t Have to Hurt has a bunch of great foot exercises that help flex the muscles that might be sore after walking in heels — things like drawing the alphabet with a pointed toe, or spending a few minutes, barefoot, trying to pick up a pencil with your toes. I would heartily recommend the book if only for that section! YogaToes can also be miracle workers after a long day in heels or on your feet.

Finding Great Deals for Shoes: (sister site to Zappos) has a lot of great deals on shoes, including regular Cole Haan Air sales; you can also occasionally find good deals at Bluefly, DSW (Designer Shoe Warehouse), Last Call by Neiman Marcus, or Sierra Trading Post. Amazon has some killer deals, but the site can be difficult to navigate (here’s a link to the “at least 50% off” section for pumps). I highly recommend using Shop It To Me if you only want to know when specific brands hit a specific price range,  ShopStyle alerts if you are stalking a particular brand or Shopping Notes if you’re stalking a particular shoe. (Read my other internet shopping tips.)

Commuting in Heels? Although some rockstars can walk for miles in their five inch heels, don’t worry too much if you can’t. While some people who walk to work prefer to wear wedge heels, my personal secret has always been to have a pair of commuting heels like Clarks or Danskos that are nearly the same height as my office pumps, and then switch into the prettier ones at work. If you prefer to commute in flats, though, there are products that help you fix your hem, such as Zakkerz. (Check out our guide to hem lengths for thoughts on which lengths look best which what kind of shoes.)

The Coporette Guide to Hems

Finally: Shoes are so much more comfortable (and last longer, and look better) when they’re properly taken care of — don’t skimp on shoe care.

* Please remember that peep-toe shoes are not appropriate for every office; same with knee-high boots and shoes with heels higher than 3.5″
— we’ve even addressed whether Louboutins are appropriate for the office, and talked about metallic shoes. Also, don’t forget to check out our @corporettedeals Twitter stream for deals on shoes and more.

Readers, which brands are your favorite for comfort? Do you have any tips and tricks for making high heels more comfortable?


Liked this article? Don’t forget to check out other Corporette shopping guides, or The Corporette Bargains page.

Not pictured: Shutterstock / Martin Novak.


  1. constructlawgirl says:

    Kenneth Cole Reaction, the 9 to 5 line are the best! I’m wearing a black pair right now and the cushioning is luxe on my feet despite the 4″ heel! Highly recommended at around $200/pair.

  2. after purchasing my first pair of cole haan nike pumps last spring, i will never again buy another heel; they are so incredibly comfy yet classic. i would recommend them to everyone.

  3. Alison says:

    A few friends of mine recommended the Alfani Step ‘n Flex line from Macy’s. I was skeptical, but they (Gracie and Denny pumps) were so comfortable from the first minute I tried them on. I have yet to put them through the test of walking marble floors at my new workplace or go through an entire day with them, but they come well recommended from many other friends.

    Best part, they’re one of Macy’s “everyday values” at $59.98.

  4. mamabear says:

    As I mentioned in the other thread, I have found Farylrobin heels quite comfortable. They don’t have a ton of cushioning, but they are well made and the heels are usually sturdy. They are of a style – rather than classic stilettos – with a chunkier heel most often, but I could walk blocks in them. A bonus is that the wider heels won’t get stuck in sidewalk cracks and the like.

  5. anonymous says:


    • I couldn’t agree more. My go-to black heels are Naturalizer, and I have a couple of cute pairs. They’re all VERY comfortable.

    • I’m a Naturalizer fan, too. They are quite comfortable and very reasonably priced, especially if you wait for sales and promos. Though, I can’t wear even their heels anymore (nothing over one inch) due to arthritis in one of my feet.

      • I’m a Naturalizer fan, too, but missed the one’s made in the 80’s/90’s that were lined in nylon tricot, and had the stretchiest leather, and felt so soft to wear all day long!

  6. stpetegirl says:

    Can anyone rec comfortable heels for high arches? I’ve found some luck with the Nurture brand from Dillards along with some Foot Petals Arches inside, but I am wondering if anyone makes heels with arch support. (Also important would be a price tag under $300, with extra points for being under $150!)

    • a lawyer says:

      Cole Haan Nike Air for the most part have good arch support. I stick with 2-2.5 inch heels.

      • Anonymous says:

        I have the world’s highest arches. I find arch supports are only helpful in flatter shoes. In heels, I just need to find a pair that fits well and provides all-over support. A very strong and stable shank is particularly important when you have high arches. Generally, Stuart Weitzman seems to be the best overall line for my high-arched foot, but the brand is at the edge of your price range. The 9-West Nuncios are super comfortable, very attractive, and less than $75.00, sometimes much less. Finally, when you can afford Prada someday, they are fab. (Very expensive shoes have very strong shanks; try on a pair of Jimmy Choos or Manolo’s and you’ll see what I mean.)

    • foot surgery girl says:

      Sofft work great because they have extra padding under the ancle.

      Also, try these inserts which have a “gel – bubble” under the arch and make my extremely high arches and weak ancles feel great with many shoes that would not be supportive enough otherwise:

  7. Ann Taylor pumps.

  8. BC from SoCal says:

    I have been in search of the perfect pair of pumps forever. I want to buy something not made in China, that has a 2-3 inches heel, no chunky heel or super skinny heel, no toe cleavage, somewhat wider shoes than a size medium, but wide. Is my list too long? I must have weird feet.

    • I’m also a Corso Como fan. See here: I believe they’re made in Brazil. They don’t always have an appropriate pump every season, but I check back often. When available in other brands I usually opt for wide sizes, but medium width works for me in these shoes.

      • I like corso comos, but the last pair of flats I bought were way too tight across the ball of the foot. I don’t wear wide sizes, either. Maybe it was just an off pair.

        Chie Miharas are always comfortable, but I can’t speak to whether they have wide sizes. I think they’re spanish? They are a little funky, not for everyone, but the heel is never skinny or chunky.

  9. BC from SoCal says:

    Oh, I forgot to state, these pumps must be comfortable and do not make too much noise while walking on tile floors.

  10. Ann Marie says:

    No one has mentioned Fitzwell; is that not a common comfort brand? I bought a pair of 2.5″ Fitzwell Player pumps a while back. The brand has a range of styles, from pointy heel/stiletto to chunky/clunky, but the prices are great. My pumps are extremely comfortable and very classic, bordering on boring, which is great for upcoming interviews. I’d like to get more pairs of pumps from them (higher heel/pointier toe), but it would be nice to get confirmation that others find them comfortable at the 3″+ heights.

  11. Seychelles have not been mentioned yet. They are the most comfortable heels I own (and I own a lot ;p).

    They are well-padded, stylish, have rubber soles so I don’t slip on polished floors and the prices are very reasonable.

  12. I stumbled upon the Nurture brand at a Dillard’s about a year ago. I loved the padding in the shoes so much that I walked away with 4 pairs. They are cute, and so comfy! I have even run in my heels! There’s so much padding in the sole that it’s able to adjust to the shape of your foot. They are also reasonably priced. These are my go-to shoes for when I need a basic, every-day shoe. I highly recommend these!

  13. I have been really happy with a couple of pairs of Corso Como shoes. They have a really nice leather padded footbed with a lot more padding than most shoes.

  14. You by Crocs are amazing!

    The look absolutely nothing like Crocs, but carry the Crocs comfort. They tend to run about $100 for heels and about $200 for knee-high heeled boots. I’m happy to have found them and readily recommend them.

  15. Theresa says:

    I am always in search of a perfect pump. My best pair right now is a pair of Me Too wedges – I swear I could walk in these all day.
    I just wish I’d bought them in red while they were still available. The patent pewter is cute but too close to black. They do give a little toe cleavage but they are so cute and comfortable I don’t care. They are also the first pair of pumps I have been able to comfortably wear both with and without stockings.

  16. Ecco. The style can often lean toward the clunky, but occasionally you can spot a good work shoe. I bought a pair of Ecco pumps after recovering from a pretty severe ankle break – for a long time they were the only non-flat shoe I could wear. Not only comfy all day long, but even after wearing them almost daily that year, they still look great!

  17. Coaster says:

    This is such a great list. Stewart Weitzman and Cole Haan are my general go-to brands, but I’ve also bought some pretty nice shoes from Ara, David Tate, and Easy Spirit (they do actually make a few stylish pumps).

  18. ROCKPORT PILOT PUMPS. Enough said. They are AMAZING and at least half the price of Cole Haans.

  19. Only have the one pair, but I’ve found Paul Green to be exceedingly well-made. Comfortable for their height and style, and I’m super picky.

  20. If price is no object, I recommend Thierry Rabotin ($400 +). Beautifeel are wonderful, but a bit pricey ($200+). Munro American makes very comfy shoes you can buy for less than $200, but they are generally best with pants. There are so many more comfort shoe brands today than there ever used to be. It’s wonderful!

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