Tested by Walking a Mile

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I live in New York City, so I’m always walking. Most days, I walk about two to three miles between walking my dog, running errands on foot, and walking to and from the train. Because NYC requires so much walking, most people’s everyday uniform includes some sort of sneaker. But not me. Not only am I always trying to add a little bit of height, I’m also always walking around in dresses during the summer. And no matter how trendy the dress and sneakers look is, I would much prefer to wear heels.

So I embarked upon the ultimate test: the quest to find the most comfortable heels in every category. After trying dozens upon dozens of different heels (and getting dozens upon dozens of blisters), I’ve finally found the best of the best.

How I tested for the most comfortable heels

For the research part of my testing, I scoured the internet to find out which brands and styles of shoes people were raving about. I went deep on Reddit threads, asked my coworkers and friends for their recommendations, and talked to shoe experts. This gave me a starting list of over 40 individual pairs, with brands like Naturalizer, Inez, and Vivaia coming up over and over.

Then, I tested the heels for myself. Armed with my phone’s step counter, I tried to walk a mile in each of the recommended heels. In some heels, I could scarcely walk down my street without getting pain or blisters. None of those made the list.

But after months of testing, I came up with a list of stellar heels that were comfortable for the entire mile walk and more. Over the past year-and-a-half, I’ve tested over 80 heels and counting. I’m constantly trying out new brands and new styles that promise comfort.

These are the heels that have past the mile walk test with flying colors.

For more of our rigorously-tested shoe coverage, see our articles on the best walking shoes for women and the most comfortable boots.

Top five most comfortable heels

naturalizer joy dress sandal

Naturalizer Joy Dress Sandal

These sandals get our hard-won most comfortable heel overall award because of their brilliantly contoured footbed (seriously, you have to try it to believe it), straps that won’t give you blisters, and huge variety of colors.

Mia Inez

Inez Mia

As a style editor, believe me when I tell you that Inez is one of my absolute favorite brands for shoes that are miraculously comfortable and completely stunning. Seriously, I don’t know how they do it — but I do know that these slingbacks are some of their best work when it comes to style and comfort.

dream paris chunky heel

Dream Paris Chunky Low Heel Pump Sandals

These Dream Paris sandals have a whopping 24K reviews and four stars on Amazon. We put them to the test ourselves and agree with all the rave reviews about their comfort and walkability — and the best part is that they’re under $40.

Wedge sandal

Vivaia Stacey Pro

“I wore Vivaia’s lightweight wedge sandals to walk across miles of hot concrete, and the ventilated cushions were so plush that I forgot about the metatarsal pain I usually get from wearing heels,” says Gabrielle Chase, associate style editor.

Kennedy Camel Weave

Frankie4 Kennedy Camel Weave

If you want a shoe designed for comfort, ask a podiatrist. Frankie4 was founded by a team of podiatrists who helped craft shoes that alleviate foot pain. These shoes are so neutral that I can wear them with anything and so comfortable that they feel like a Birkenstock, despite them being over two inches.


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