Shop The 15 Most Comfortable Ankle Boots You Can Start Wearing Now

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Whether you’re going to the office or out on the town, having the right ankle boot is key for a good time. Assuming you already have your knee-high boots for fall, chances are you’ll want comfortable ankle boots to balance out the mix. Fall is practically here, which means you might be slowly rotating those warm-weather dress shoes to the back of your closet as you make room for your boots collection in the front—which, of course, includes effortlessly cool ankle boots.

I’m a sucker for cute summer sandals, but there’s something about the annual return of boot season that makes me excited for the weather cool-down that comes with it. And because I’m looking forward to a new season of shoes with such high anticipation, I went ahead and found the ankle boots you’ll never want to take off—guaranteed.

The Patti Lace-Up Boot

A lace-up ankle boot is a must-have closet staple. Plus, these feature a cool block heel and are the perfect price point for an everyday ankle boot.

Sizes: 5-11

Colors: True Black, Warm Cinnamon, Rusted Burgundy

Material: Leather upper

Customer review: “The leather on this boot feels like butter! They are so comfortable and look cute with skinny jeans, mom jeans, midi dresses...literally anything! The slight heel definitely gives this boot an elevated look!”

Dolly Boot In Black Suede

Platforms are the perfect way to add some height without getting the discomfort of a stiletto. This option is a fun twist on the classic black suede bootie—perfect for date night.

Sizes: 5-11

Colors: Black, Ivory, Pink

Material: Kid suede leather

Romina Ankle Boot

Talk about a quintessential ankle boot…I can envision wearing these 100 different ways. For a quality style that’s cute and comfortable, this is a great option (and one that you’ll wear for years).

Sizes: 5-11

Colors: Black

Material: Bovine Leather

Hoven H2O Boots Onyx Leather

The shape, the sole, the feel—everything about this pull-on ankle boot is just too good. I already know this will be a solid option for any closet.

Sizes: 5-13

Colors: 7 options

Material: Leather and knit upper

Customer review: “Love this style! As expected. They look good with skinny pants or bootleg pants. Size is just right. Love the color!!!”

Heeled Brushed Leather Booties

For a more luxurious look, go for these brushed leather boots. They are as cool as they are practical.

Sizes: 34.5-41.5

Colors: Black

Material: Upper with elasticized gusset and pull tab on the back, Leather lining

Zhara Crocodile-Embossed Leather Bootie

The lace-up detail on these boots is so unexpected, yet the silhouette still looks sleek and put together. Pair these with a flare or cropped denim for a super funky fall ensemble.

Sizes: 5-11

Colors: Color Eggshell, Color Black

Material: Crocodile Embossed Leather, TR lining, Tractor outsole

Customer review: “These boots a most definitely a statement piece 10/10 must recommend. Thanks Schutz 🤗”

Irie Ankle Boot

For a fresh take on a classic, opt for Sam Edelman’s Irie ankle boots. The toe shape plus the heel height gives it a cool-girl feel.

Sizes: 5-12

Colors: Chocolate Brown, Modern Ivory, Bright Dahlia, Silver, Black, Lux Tan Suede

Material: Leather, Insole: Synthetic

Chunky Chelsea Boot

A Chelsea boot can take you from the office to the bar very easily. The faux suede on this is the perfect touch to make these look so much more expensive than they really are.

Sizes: 4-11

Colors: Dark Khaki Green, Black

Material: Lining: Polyester 100%, Sole: Thermoplastic rubber 100%, Sock: Polyester 100%, Upper: Polyurethane 100%

Free People Brayden Western Boot

Come on Barbie, let’s go party! These boots are perfect for your Barbiecore era. Cowboy boots are continually on trend and make for the perfect addition to any ensemble.

Sizes: 36-39.5

Colors: 6 options

Material: Leather upper and sole, etched metal toe

Customer review: “I’m usually 37 1/2 and I ordered a 38! These boots are true to size I will be exchanging them for a 37 1/2 Love the boots! Make my legs look amazing.”

Jadon Boot Smooth Leather Platforms

A favorite among our editors, these combat boots are so comfortable, they’ll never leave your feet. I have had my pair since my mother got hers when she went abroad in the ’80s. You will have these for generations, literally.

Sizes: 5-12

Colors: Black Polished Smooth, White Polished Smooth, Red Polished Smooth

Material: A twist on the classic Dr. Martens leather: durable, with a smooth and polished finish.

Customer review: “LOVE THESE BOOTS, TOO!!!!!!!!!!! I've been a Dr. Martens fan since the early 80s. I still have many of those pairs from 40 yrs ago!!! I'm rolling at approx 150 pairs currently!!!!”

Square-toe Water Repellent Bootie

A classic, yet cool, shoe. The square toe and geometric heel shape on these will step your ankle boot game up.

Sizes: 5-11

Colors: Black

Material: Upcycled materials

Customer review: “Good quality and comfortable.”

Willa Boots

I personally own these and cannot think of a better, cooler, and more effortless shoe. The heel is the perfect day-to-night height to work with all your go-to fall ’fits.

Sizes: 36-41

Colors: Black

Material: 100% cow leather

Geist Square Toe Boot

I love a good brown boot in the fall. It’s an awesome transition shoe that will make you want to go apple picking or tour a winery.

Sizes: 5-10

Colors: Black, Brown, Black Neoprene

Material: Leather upper and lining/synthetic sole

Customer review: “These are the most comfortable boots ever! Soft leather unlike brand new leather shoes. Inside is also soft to walk. True to size.”

Angel Alarcon Pointed-Toe Boots

This style has everything you need for a perfect ankle boot: a comfortable material, a low heel, and an edgy shape. Sure, the silhouette may be simple, but it’ll go with everything.

Sizes: 36-41

Colors: 6 options

Material: Faux leather upper, insole

Customer review: “The leather of this shoe is like that of a marshmallow. It’s a gooey, soft leather. I haven’t worn them yet, I did try them on and I am convinced; my feet will welcome the feel of comfort that these boots afford.”

Classic Ultra Mini

Spotted on It girls like Bella Hadid and Kendall Jenner, these cozy Uggs are both comfy and cute. Pair the Ultra Minis with jeans, workout clothes, or sweatpants for an easy, casual fall ensemble.

Sizes: 5-12

Colors: 13 options

Material: Leather bottom, real sheep upper

Customer review: “This should have been my go-to boot for the fall. Loved the color selections. However, I have a normal foot shape...I’ve worn & loved UGG products for years...and the opening on this boot is too tiny for my foot. Had to return them.”

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