Comfortable Shoes at Every Height

Jessica Simpson Mandalaye Elastic Ballet Flats

 This post is inspired in part by an article on Racked about the most comfortable shoes owned by “people who are on their feet all day.” As the author notes early in the article, most of the recommendations are more functional than attractive. Among the recommended shoes are Born and Danskos clogs, Sam Edelman flats, Blundstones and Bog boots, and Nike sneakers.

I usually preface my shoe recommendations with “feet are too different to generalize, BUT,” because shoes follow only one part of the Anna Karenina principle, in that every uncomfortable shoe is uncomfortable in its own way.

Unlike the practical people interviewed for the aforementioned Racked piece, I value form more than I value comfort, though in recent years the scale has gradually tipped in favor of comfort. So my goal here is not to recommend the most comfortable shoes you can possibly find, but the shoes recommended here are comfortable enough to walk reasonable distances in, without any compromise on “style.”

Cole Haan Tali Bow Ballet Flats


When flats-shopping, it’s important to remember that lack of height does not imply comfort. As with all shoes, the right fit is key. Often that means avoiding attractive keywords like “pointed toe” for people with wide feet, or “strappy” for those with bunions. Make peace with your feet (and issues specific to you) and be realistic in your expectations. From there, there are a few things to look for: rubber sole, a wedge that suits your arch, padded sock lining (preferably leather), and an elastic collar–this is important because friction is the enemy of comfort, and the right type of elastic collar secures the shoe to your feet without constricting them. My favorite flat, the Cole Haan Tali Bow Ballet Flats (reviewed here), are so great because of the elasticized opening.

My recommendations: Nine West Zeno Flats, Miu Miu Lace-Up Ballerina Flat, French Sole FS/NY Passport Flats, Repetto Brigitte Ballet Flats,  and Jessica Simpson Mandalaye Elastic Ballet Flats.


Compared to other styles of shoe, athletic shoes as a class tend to be more comfortable. That you can wear socks (that almost eliminate friction and add padding) with them resolves most of the issues that generally contribute to discomfort. So on this front, there are fewer universal truths: I can count only mesh uppers, padded tongue and collar, a multi-layer midsole, and a contoured outsole. When it comes to everything else, your feet shape and issues will dictate which options are key: for example, cushioned shoes are good for hard surfaces, but bad for stability. And there are enough options available that you should not settle for a shoe that requires a break-in period. If you can’t leave the store or house in them immediately, move on.

My recommendations: Brooks Heritage Vanguard Sneaker, Adidas Originals Superstar Sneaker, Merrell Siren Edge Sneaker, and Converse Chuck Taylor Hi Casual Sneakers.

Report Mara Ankle Tie Sandal (also here)


There is nary a stiletto high-heel that can be considered comfortable. If you want height and comfort, shoes with block (or chunky or wedged) heels are your best bet. And when it comes to heels and comfort, it’s all about what to avoid: avoid unlined shoes (or shoes lined with coarse materials), avoid very thin buckled straps, avoid unpadded footbeds, avoid thin soles, avoid flat insoles, and avoid stiff materials/leathers. When it comes to non-leather soles/heels, avoid wood and opt for cork or raffia.

If you only like stiletto heels, look for shoes with platforms; they sometimes make 5″ heels feel like 3″ heels. And before deciding to keep a pair of shoes, try them on at least once near the end of the day when your feet are at their most swollen.
My recommendations: Salvatore Ferragamo Elinda Block Heel Pump, Vince Blake Sandal, French Sole Trance Pump, and Valentino Rockstud Espadrille Wedge.


Sometimes, despite having accounted for every conceivable fit issue, a shoe will still fail you at a critical moment; at that point you just have to work on your own fix. Keep on hand the following: shoe pads, replacement insoles for your arch, athletic tape (to prevent or cover blisters), moleskin, and anti-blister balm.

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