We're Fashion Editors—These Are the Most Comfortable Heeled Boots We Own


(Image credit: @joiedejude)

One thing about fashion editors that you could likely guess for yourself is that we own a lot of shoes. The walls of my apartment are currently lined with them. Winter-boot season is particularly difficult on my New York–sized closets. Despite the impressive quantity I have in the boot department, I always find myself gravitating toward a few comfortable pairs that I know can never fail me. 

My co-workers have told me they're the exact same way. Once you've broken in a good pair that you can walk in for miles, you never want to take them off. I prefer heeled boots because they're so much more comfortable than stilettos. If you're in the market for a new pair, anything fashion editor tested and approved will never disappoint. Shop our editors' favorite pairs below.


(Image credit: @_sierramayhew)

Okay, I'll go first. My answer comes as a bit of a surprise to me because, out of all of my designer boots, this under-$200 pair has officially won me over. It's definitely the most worn pair of shoes in my closet because I can walk anywhere in them. When I first received them, I knew it was time to donate the shoes I own that look similar because these were just too good.


(Image credit: @_sierramayhew)

Shop Sierra's pick:


(Image credit: @katcollings)

"Paige shoes are unlike literally any other shoe I have ever tried when it comes to the comfort factor. It sounds odd, but they are comfier than sneakers. They have the plushest insole that literally feels like heaven to step on. I don't understand it, but my happy feet aren't asking questions. The shoes I'm wearing are the Willa style, but the Lucy is newer and similar. All the brand's shoes have its signature insole, so you can't go wrong!"


(Image credit: @katcollings)

Shop Kat's pick:


(Image credit: @copelynshaw)

"My heel tolerance prior to these boots was flatforms, so to say I can make it through a whole night in these is a testament to their comfort. The soft leather is super luxe, and the heel height is ideal for long wear."


(Image credit: @copelynshaw)

Shop Copelyn's pick:


(Image credit: @allypayer)

"These BY FAR boots are a longtime favorite of mine. The leather is so soft, and I've yet to get a blister from them, even if I walk for miles."


(Image credit: @allypayer)

Shop Ally's pick:


(Image credit: @joiedejude)

"It's hard for me to wear anything other than Neil J. Rodgers' boots. The Eva Slouch is one of my favorite styles because not only do they look effortlessly chic—exuding a French-girl vibe—but they're also so comfortable. They're made from buttery-soft black Nappa leather and have a perfect two-inch heel height. I wear these on repeat with jeans, dresses, skirts… You name it."


(Image credit: @joiedejude)

Shop Judith's pick:


(Image credit: @anna__laplaca)

"I'm not sure what the brand puts in its shoes, but every pair I own from Vagabond is the comfiest pair ever. That said, its knee-high Hedda boots might take the cake. I'm not exaggerating when I say that I wear mine at least three times a week while running around NYC. I've had them for three years now and walk 20,000 steps a day, so you do the math."


(Image credit: @anna__laplaca)

Shop Anna's pick:


(Image credit: @gracejoshua13)

"These Schutz boots are my favorite for so many reasons. I love Western and thigh-high boots, and these are like my two favorites had a baby. The stiletto heel may look intimating, but these are surprisingly comfortable. I wear them to work, to nights out… You name it, and I'm probably wearing these. They work with everything too. I style them with minidresses, skirts, and jeans on repeat."


(Image credit: @gracejoshua13)

Shop Grace's pick:

Shop more comfortable heeled boots:

Up Next: These Are the 5 Types of Jeans I'll Wear in 2023, Plus the Styles I'll Toss

Associate Editor

Sierra Mayhew was always destined to work in fashion, but she didn't know it at first. Growing up with no choice but to wear a rotation of school uniforms and activewear, her love for fashion really blossomed when she moved away for college and was able to finally define her very own personal style. Shortly thereafter, she interned at Elle magazine and instantly knew that editorial was for her. After graduating from the University of Notre Dame, she worked for ShopBazaar, contributing regularly to Bazaar.com, and finally made her way to Who What Wear, where she is an associate editor. When she’s not working, you can catch her always trying to catch a flight, rollerblading through New York City traffic, or exploring the latest luxury vintage boutique.