This shopping guide for comfortable heels is inspired by one of our all-time top posts, The Quest for Comfortable Heels. We update the text of this page regularly and welcome you to add your on-topic comments as well. Last updated: February 2016.
Forget the Holy Grail — the quest for comfortable heels can be a lifelong hunt for some women. In general, if you can find one pair of shoes you like, try other shoes from that brand (although there can be variances within that brand as well). Note that for interviewing, you should be able to walk a few blocks in your heels comfortably; I would say the same for your first day on the job as well as any big meetings (since you may walk to lunch at a local restaurant). Of course, flats are acceptable for interviewing and beyond, as well!
Brands for Comfortable Heels
The brands of heels most often touted as comfortable can be broken down into four price ranges, and then into two categories: The first group holds the stylish/trendy brands that everyone swears by for comfort (whether or not they’re marketed as “comfort shoes”), and the second group of shoes are marketed for comfort but often a bit funky/clunky when paired with, say, a pencil skirt. For specific shoe recommendations other than those pictured below (both from Kat and the readers) check out our regular Hunt feature (in which we hunt for one wardrobe basic or basic accessory in a range of prices) and our afternoon Coffee Break posts (which often feature shoes); you may also want to check out our post on upgrading your shoe collection.
- Designer heels: “Investment shoes” such as Christian Louboutin (but please know your office before considering thick platforms or 4″+ heels), Jimmy Choo, Manolo Blahnik, and Miu Miu (one of the favorites in our Newbie Guide to Designer Shoes)
- Special mention for comfortable (but pricey) professional flats: Chanel.
- Mid-Range heels, $200-$500:
- Stylish/trendy but reportedly comfortable: The hands-down reader favorites are Stuart Weitzman and Salvatore Ferragamo — also try Anyi Lu, Attilio Giusti Leombruni (particularly for flats, but they make heels too), Cole Haan, Kate Spade (the brand’s wedges are apparently a favorite in DC), L.K. Bennett (the Sledge pump is a Kate Middleton favorite), SJP by Sarah Jessica Parker, and Taryn Rose (founded by an orthopedic surgeon).
- Designed for comfort, but may be funky or clunky, depending on your taste: Arche, Beautifeel, Earthies, Eileen Fisher, FLY London, Gentle Souls (by Kenneth Cole), John Fluevog, Oh! Shoes, Pikolinos, Think!
- Special mention for comfortable flats in this range: Attilio Giusti Leombruni, French Sole, Paul Mayer, Salvatore Ferragamo
- Affordable heels (under $200):
- Stylish/trendy but reportedly comfortable: Donald J Pliner, Franco Sarto, Geox, Isolá, Peter Kaiser, Sam Edelman (particularly the Okala), Sofft, UKIES
- Designed for comfort, but may be funky or clunky, depending on your taste: Aravon, Børn, Camper, Clarks (particularly the Indigo or Artisan lines), Cobb Hill (by New Balance), Dansko, Ecco, Josef Sibel, Miz Mooz, Munro, Ros Hommerson, Tsubo, Umberto Raffini shoes at The Walking Company
- Special mention for comfortable flats in this range: Børn, BP, Ivanka Trump
- Budget-friendly heels (often under $100): Anne Klein (particularly the iFlex line), Bella Vita, Comfort Plus by Predictions (at Payless!), Corso Como (ladies love this $98 pump), Fitzwell, reader favorite Merona wedge heels (at Target), Soft Style (by Hush Puppies), Sole Society, and Trotters. 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 N5 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: We’ve mentioned a few brands or styles for comfortable flats in each price range, above — do 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, 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. In our more recent Hunts, we also try to include picks for wide/narrow widths, extended sizes, and (for boot round-ups) wide and narrow calves.
Pictured below, a few of our (and readers’) perennial favorites:
- Michael Kors Flex Pump ($99) / Stuart Weitzman / Kate Spade New York ($298) / Calvin Klein / Christian Louboutin ($675) / Comfort Plus by Predictions ($29!)
Avoiding Pain in Heels
Alleviating Pain Caused by Shoes, During: Inserts can make a big difference with heels! I’ve liked Insolia inserts (read my review here), as well as Dr. Scholl’s and Foot Petals. (Insolia inserts really make a difference — something about the slim pieces of plastic helps my flat feet feel more comfortable in heels.) Note that some shoe maintenance (such as asking a cobbler to put rubber soles and rubber heel tips on your new shoes) can increase comfort as well as extend the life of your heels. 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: YogaToes can also be miracle workers after a long day in heels or on your feet. 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, for example, 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!
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 women 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 adjust 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 to make your shoes last longer, and take steps to keep your shoes odor-free.
If you know the exact name of the brand or the style name you’re looking for, Amazon is hard to beat — they often have sale shoes in lucky sizes for steep discounts. Otherwise, though, the site can be hard to navigate — if it’s helpful, here’s a link to the “at least 50% off” section for pumps. Beyond that, 6pm.com (sister site to Zappos) has featured sales every day, and Nordstrom shoe sales are hard to beat. You can also occasionally find good deals at Bluefly, DSW (Designer Shoe Warehouse), Last Call by Neiman Marcus, or Sierra Trading Post. 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 apps like Covvet if you’re stalking a particular shoe. (Read my other internet shopping tips.) For pricier shoes, resale sites like eBay or The Real Real can be a great way to get lightly used merchandise at a good price (but proceed carefully).
* Please remember that peep-toe shoes are not appropriate for every office; the same goes for shoes with heels higher than 3.5″ and knee-high boots. We’ve even addressed whether Louboutins are appropriate for the office and talked about metallic shoes. Also, don’t forget to check out @corporettedeals on Twitter 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?