Guide to Comfortable Heels

This 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: January 11, 2012.
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). (Pictured above: Cole Haan – Air Talia Pump (Black Leather) – Footwear, available at Zappos for $198.)
Brands for Comfortable Heels: The brands of heels most often touted as comfortable ones can be broken down into these sorts of categories:
- Designed by master craftsmen, incredibly comfy, but incredibly pricey: the usual suspects: Manolo, Louboutin, Choo
(I’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 ($200-$500): Cole Haan Air
, Stuart Weitzman
, Taryn Rose
(the brand is designed by a orthopedic surgeon!), Salvatore Ferragamo
, Donald J Pliner
- Funky or clunky, depending on your taste, but comfortable investments: John Fluevog
, Frye
, Born
- Lower-cost comfortable (more likely to be classic or slightly trendy): Isolá
, Franco Sarto
, Sofft
, Geox
, Peter Kaiser
, Sudini
- Lower-cost comfortable (but also often clunky): Clarks
, Beautifeel
, Tsubos
, Dansko
- Particularly great for high-heeled winter boots*: Aquatalia by Marvin K.
, La Canadienne
(most are waterproof!)
- Mall stores that bring trendier shoes to you at a more reasonable price: Aerosoles, Link to Zappos.com Brand Pages.
Readers have also called out Joan & David Circa and Enzo Angiolini
.
as well as Nordstrom’s brand Linea Paolo (no longer available as of January 2012).
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 CitySlips
, Footzyrolls
, 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! Yoga Toes
can also be miracle workers after a long day in heels or on your feet.
* 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″. 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?
Also, please don’t forget to check out other Corporette shopping guides!



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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!
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).
ROCKPORT PILOT PUMPS. Enough said. They are AMAZING and at least half the price of Cole Haans.
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.
Thanks for a informative material; I enjoyed it very much. Hollis Pana
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!
I LOVE Ivanka Trump. I have her Indico pumps in several colors. And I have to 2nd Cole Haans. They are beautiful, and last forever when well taken care of.
When I travel for work I’ll spend a good 16 hours on my feet (or more if I’m at a dreaded trade show) I have to go with Naturalizer. Nothing else will do on those days.
For the funkier corporettes DV by Dolce Vita makes incredibly comfortable platforms! Love mine!
I think one of the hardest things about finding comfortable heels is, height of the heel aside, I’ve got small feet. I’m a size five foot and even in that case, my feet have almost a half-size difference between them. I can and (sometimes) do wear kids’ shoes because they fit better – but when I want heels, a shoe that might be painful becomes one that doesn’t fit and is definitely painful on me.
Most mall stores don’t even carry my size – stores like Wal-Mart (crappy quality, incredibly cheap) are sometimes my only choice, given that my budget doesn’t accommodate designer shoes yet.
Sofft shoes are my go-to brand for work! Like walking on air.
I’m new to this site and building my wardrobe for a conservative office and have a few shoe-related questions:
1. How high is too high? I prefer cone-shaped mid-low heel (2.5 inch max) but am finding this to be quite limiting in terms of style and colour.
2. I have lots of black and dark brown shoes and want to expand. Is bone or beige inappropriate office wear?
3. What color shoes is appropriate with a navy/almost black shift dress?
4. What color shoes is appropriate with a dark brown pant?
Thanks! :)
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