I Don’t Wear Heels, But I’m Willing to Compromise for These 32 Boots

I’m not one to compromise when it comes to comfortable footwear. New York City commuting, double ankle surgery, and a few too many wrong steps off the curb keep me humble when it comes to heel heights. So I usually resort to cushy sneakers, lug-sole boots, or chunky loafers with the exception of flatform-style wedges for the evening. 

Although I love the look of nice heeled boots, they’ve never been for me for the previously stated reasons. This fall and winter, however, kitten-heel boots have been increasingly popular, and I acquired a pair that changed my mind about the validity of these incredibly moderate heel heights. Designers such as Khaite, Prada, and Dior have been endorsing the kitten-heel trend, and many others have followed suit. 

I’ve channeled all of my sore ankles and barefoot walks home into the below shopping list of the most comfortable kitten-heel boots on the market.

Elevate your winter looks with these cream croc boots. 

Zebra-print boots are on my list, and this pair offers the ideal low heel. 

Crisp white leather boots are undeniably cool.

These micro-heel boots ensure daylong comfort.

Soft suede blankets these tan kitten-heel boots.

Just because the heel is low doesn’t mean they have to be boring. 

I’m in love with this black-and-white cow-print version.

Casual slouchiness makes these minimal boots.

These boots are a rare any-occasion piece.

These modern boots have a pretty sculptural shape. 

Black-and-white color-blocking is the chicest addition to these ankle boots. 

The flared heel of these boots adds extra-comfortable support. 

Dream boots, period.

Supple red leather for all fall and winter. 

A dupe for the cult-favorite Khaite boots is these Western kitten heels. 

These slouchy suede boots are perfectly effortless.

Statement boots don’t always have to be extra-high stilettos. 

Naturalizer is known for comfortable footwear, so these are a shoo-in. 

Sleek, modern, and painless.

Upgrade kitten-heel boots with sophisticated prints and textures.

These red stunners are holiday ready.

Guaranteed match-everything booties. 

This low, angled heel is a city commuter’s dream come true. 

Chocolate suede is as chic as it gets. 

Under your trousers, jeans, or a maxi dress

These are the influential boots that changed my stubborn sneaker-wearing ways. 

A uniquely sculptural heel adds interest to these black boots. 

This thicker heel offers extra stability for a slightly higher height. 

Simple booties in rich honey-colored faux leather. 

Tonal green suede will go far in your year-round wardrobe. 

A shapely and low heel guarantees easy days in these ankle boots. 

The clean silhouette is key for these sleek black booties. 

Next: These 3 Classic Boot Styles Are Here to Stay in 2023 and Beyond