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: 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).
- Pricey: Christian Louboutin (but please know your office if you’re considering thick platforms), Jimmy Choo/>, Manolo Blahnik, and Miu Miu (one of the favorites in our Newbie Guide to Designer Shoes)
- Mid-Range, $200-$500:
- Stylish/trendy but reportedly comfortable: The hands-down reader favorites are: Cole Haan, Stuart Weitzman, and Salvatore Ferragamo – also Anyi Lu, Attilio Giusti Leombruni, Kate Spade (their wedges are apparently a favorite in DC), L.K. Bennett (the Sledge pump is a Kate Middleton favorite), and Taryn Rose (founded by an orthopedic surgeon)
- Designed for comfort, but may be funky or clunky, depending on your taste: Arche, Beautifeel, Earthies, Gentle Souls (by Kenneth Cole), John Fluevog, Oh! Shoes, Think!
- Affordable (under $200):
- Stylish/trendy but reportedly comfortable: Donald J Pliner, Franco Sarto, Geox, Isolá, Peter Kaiser, Sofft
- Designed for comfort, but may be funky or clunky, depending on your taste: Børn, Camper, Clarks (particularly the Indigo or Artisan lines), Cobb Hill (by New Balance), Dansko, Ecco, Miz Mooz, Munro, Ros Hommerson, Tsubo, Umberto Raffini shoes at The Walking Company
- Budget friendly (often under $60): Anne Klein (particularly the iFlex line), Comfort Plus by Predictions (at Payless!), Fitzwell, reader favorite Merona wedge heels (at Target), and Soft Style (by Hush Puppies). Read our other tips on great shoe bargains, below.
- Particularly great for high-heeled winter boots*: Aquatalia by Marvin K., Frye, La Canadienne/> (most are waterproof!)
- Mall stores that bring trendier shoes to you at a more reasonable price: Aerosoles, Easy Spirit, Naturalizer (particularly their N-5 or Naya lines), Rockport (many of their shoes use Adidas technology for shock support and comfort)
- Brands that you can still find on eBay: Cole Haan Air (from Cole Haan’s late, great collaboration with Nike), Hollywould, Linea Paolo, Sacco, Sudini
- Comfortable flats: Check out our previous discussions on comfortable flats and flats for job interviews, as well as our best tips on how to look professional if you ONLY wear flats (it can be done!).
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.
Pictured below, a few of our (and readers’) perennial favorites:
- Michael Kors Flex Pump ($99)
- Stuart Weitzman Platswoon ($340)
- Kate Spade New York Karolina ($298)
- Calvin Klein Diema ($69)
- Christian Louboutin’s Simple Red Sole Pump ($675)
- 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: 6pm.com (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.)
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?