The 20 most comfortable heels and heeled boots, tested over a year of extensive walking

Written by Samantha Crozier; edited by Sally Kaplan Updated Nov 1, 2024, 1:24 PM GMT-7

 

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.

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.

 

Highest heel: Elizee Fiorella Sandal

 


Samantha Crozier/Insider

 

At nearly four inches with a three-inch pitch, these shoes look a little intimidating — but don't let that fool you. They're super lightweight, with a cushioned insole and a thick strap that wraps around your ankle for stability. 

When I wore them for the first time, I was blown away by the construction. This is a true stiletto heel. And yet, I didn't feel any of the discomfort of basically walking around on my tippy-toes for hours. 

It's a little on the pricier side, but it's a perfect choice for a wedding — whether it be yours or one you're attending as a guest. It has the rare combination of being a classic, formal stiletto while also being a shoe that you can dance in all night. 

Just not that when I first tried this, I had buckled it too loosely around my ankle. It felt much less comfortable because my foot was wiggling around too much. Make sure you fasten these on tightly (even tighter than you think you need to) for the best fit.

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