When shopping for a new pair of cute boots, there are few things to consider: The most comfortable ankle shoes will have a sturdy sole, a roomy-enough toe box, and ideally, a padded footbed.

These cute ankle boots combine a fashion-forward wedge heel with the comfort of a Dr. Scholl’s insole to create a supremely supportive bootie with a designer look.

And besides being cute, those laces actually team up with the side zippers to prevent ankle injuries —a must for long walks. One Zappos customer says “These are the most comfortable boots I ...

An age-old, timeless wardrobe essential. Whether you're more of a black ankle boots kinda person, or would definitely opt for one of the bolder, colourful designs in this edit, there's a boot for all.

$148 at Naturalizer The details These waterproof ankle booties from Blondo are a fall and winter wardrobe staple — and they're currently on sale for under $150. With their sleek ankle boot silhouette, ...

Cute side panels of bold black-and-white checkerboard adds some flair to these round-toe boots. You’ll love the chunky soles (comfy and edgy!) and the pull tab design makes ‘em a cinch to slip ...

Parade aims to feature only the best products and services. If you buy something via one of our links, we may earn a commission. We love all of our boots equally, but certain styles are suited for ...

Reader Andrea writes, "I just purchased a pair of black ankle cowboy boots, but I'm not exactly sure of the best ways to wear them. Any style solutions?" We've a few cute ways to wear 'em--and ...

11 White Boots You Can Wear With Anything in Your Closet target.com Stylish Black Boots: Allegra K Chunky Heel Ankle Boots Fall and low-rise black booties go together like peanut butter and jelly.