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Killer kicks that won't kill your feet.
When it comes to shoes, comfort is super important. Trust me, this is coming from a girl who has worn heels since my preteen years (I take pride that I can even run in 'em), but now, I'm listening to my body and have focused on finding fashionable options that give my feet a break. If you're a stiletto-lover like me, I've got some good news: Sneakers (thankfully) aren't our only options for getting some relief while pounding the pavement, thanks to all the cute and comfortable ankle boots out there. Fashionable and functional, our fave ankle boots are stylish and super versatile so you can wear 'em anywhere, yet also durable, cushioned, and supportive. Whether you have a job that keeps you on toes (literally), you simply love to walk a lot, or you're prone to aching feet, you'll be happy to discover these fab picks.
Ahead, we've scouted around for the cutest ankle boots that are truly made for walkin' (and stuntin'), throughout the fall and beyond, since you can wear them year-round (yes, even summer). Plus, they're easy to store, and they look good with jeans, skirts, and dresses (so basically, everything). The colder seasons are when ankle boots really have their time to shine, so add some to your closet before fall kicks off with these 18 standout options.
These pale blue bbs with the coolest angular heel shape are a total compliment-magnet. Seriously, have you seen a color like this on boots before?
Rave Review: "Love the color and style of these boots," writes one reviewer. "I’m a size 8 and I ordered an 8; they fit perfectly. Great quality and comfortable too. Very happy with my purchase."
Level up your shoe game with this elevated take on the Chelsea boot that sports a sleek flatform for a little extra height and cushioning from heel to toe. Rave Review: "Very comfortable and sturdy. Match with white/black/blue jeans. Runs big - I wear US size 7 in Dr. Martens and I got US size 8 based on other reviews, and they fit perfect. Color is a little bit off as it actually looks like khaki instead of beige, but still very stylish."
If you're all for extra comfort, then this sturdy suede lace-up bootie with ample ankle support and traction on the soles is a cute way to treat your feet.
A chunky spin on the combat boot is probably everything you didn't know you needed in your shoe collection. We're so here for all the different textures on this trendy style, which is lined in plush faux fur to keep you extra cozy. Oh, and it comes in brown and black, too.
Rave Review: "These boots are awesome my husband got them in bone color for me in my normal size 8," shares a reviewer. "I believe the faux fur lining helps keep them true to size. The heel height is manageable, and they are comfortable to me. Pro tip: wear them in the house 24 hours to get used to the heel height. These are super sexy. I highly recommend."
We're confident you'll brave the elements (and long days) like the fashionable pro you are in these seam-sealed waterproof Nubuck boots from Vionic, a brand that specializes in ultra-supportive, comfy (yet stylish) kicks.
Rave Review: "I bought these back in October and have been wearing them about six weeks now." writes one reviewer. "I've had several pair of Vionic shoes in the past so I knew the support was great and was confident that these would be too. The toe box seemed a bit small and the heel area seemed a bit wide but I followed the instructions and wore them around the house for a few hours at a time for about 3 days. All they needed were to be broken in. Now I wear them all day at least 3 days a week! Not only do they offer fantastic support but I have received several compliments on them. A bootie with style and comfort is certainly a winning combination!"
Feast your eyes on this gorge chocolate brown suede leather pair, tricked out with the designer's signature, curvy gold chain heel. (Kinda like statement jewelry for your feet.) It's your new everyday boot, with a twist.
This trendy patterned style is everything. Pair these showstoppers with a mini skirt or fitted jeans, and you'll be the coolest cat in the room.
The '70s called, and we are so answering. The chunky, slightly flared heel on this Brother Vellies pick adds stability, and the thick platform provides some much-needed cushioning for those days where you're running around town.
Behold: the sock boot of your dreams. Thanks to the stretchy uppers, they'll fit you look a glove, and that low block heel looks and feels amazing.
Rave Review: "I’ve been looking for a skinny ankle boot for so long and this one delivers on all accounts: great fit, superior style, awesome comfort with heel height just right," shares a reviewer. "They're so easy to pull on, too. Perfect for cropped jeans and current uplift to any dress or skirt on the closet. Yay!"
Shine like the star you are in some metallic champagne-hued cowboy boots. Love this pair's silhouette, but not the glimmer factor? These come in matte ivory, too! P.S. They're so perfect in either color for various bride-to-be festivities, from the bachelorette party to the bridal shower to the wedding after-party.
How sleek and chic are these handmade suede beauties? We're loving that softly pointed toe shape and stacked heel.
You'll turn heads in these fire engine-red leather showstoppers with a chunky mid-height heel and a small platform. I mean, just look at that color!
Telfar is a cult fave for a reason! While their killer bags tend to hog the spotlight, you can't really go wrong with any of the brand's hit designs—especially these cozy boots from the UGG x Telfar collab. They're a totally fresh twist on a ubiquitous staple.
We're loving this waterproof suede bootie's creamy shade! But if you're skeptical about keeping light-colored kicks clean, good news: these come in five other colors. These stunners work hard and play hard: they're polished enough to wear to the office, but you'll def wanna wear them for a night on the town, too. Plus, they're waterproof!
Rave Review: "I just ordered tan and brown suede in this bootie," writes a doting reviewer. "I went with my true to size and the fit is perfect. Love the soft square toe here, love the architectural heel, always love an inside zipper, the colors here are perfect & they're waterproof. I mean, c'mon! Absolute work/going out staple. Will be living in these this Fall/Winter season."
We're all about that shearling. The chunky lug sole and zipper-detailed vamp make such a great contrast.
The short silhouette and side zips on these wedges makes 'em so easy to throw on or slip off, so they'll totally be your go-to pair for running errands in colder seasons.
It's giving "miss I can do this all by myself" vibes. Conquer any task with these commanding waterproof booties that feature gorge camel suede uppers with elastic gussets, plus a treaded lug sole and cushioned footbed.
Rave Review: "When I first opened these I thought they were a little too “lumberjack” but when I wore them with some wide legged jeans, they are so cute! They are comfortable and I get a lot of compliments on them. I got a size 9, and they fit true to size."
If most military-style boots are too chunky for your tastes, you'll dig the minimalist, elegant look of this pair. Bonus: they're made with buttery natural leather sourced in Spain that'll age beautifully over time.
Cosmo’s team of digital fashion experts—which includes Fashion Features Director Rachel Torgerson, Fashion Editor Tarah-Lynn Saint-Elien, and Contributing Fashion Features Director Alexandra Ilyashov—have decades of combined experience in the industry. They spot relevant trends on the runway before they even hit your TikTok FYP or Insta Explore Page and conduct research across retailers of all kinds—testing many brands IRL—to bring you the best clothing and accessory picks for every season. Basically, we’ve curated the internet to bring you the chicest options like it’s our job (because it is, heh).
Each of our shopping articles adheres to the 15 Percent Pledge and includes products for all sizes. These comfy ankle boots were chosen based off of design style, functionality (sturdy soles are a must!), price point, size range, material (waterproof, anyone?), and so many reviews to put together this shoppable list of the very best for you!