these chelsea platforms
Vagabond Shoemakers Tara Chelsea Boot
these chelsea platforms
Vagabond Shoemakers Tara Chelsea Boot
Cons
- tops may chafe wider calves
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.
Glowing Review: “These are likely my favorite flat boots that I own. For context, I’m the girl who wears boots almost daily, and I have probably 100 pairs just of this type of boot, across many different designers and price points, so I’ve done the leg work, ha. If I had to pick the perfect general pair, using measurements like versatility, look, comfort, durability/quality etc, I think this might be the pair. They can truly go with anything, unlike some of my more outrageous combat boots. They’re of great quality, and they’re insanely comfortable… I also love that the ankle is so slim, yet at the same time, they’re super easy to get into. if you’re looking for the perfect all around black boot, you should 100% get these. (And if you have a high arch, especially, you need these in your life…no need to even size up for that) They truly rival boots at 5x the price point.”
these baby blues
Truffle Collection Block Heel Square Toe Ankle Boots
these baby blues
Truffle Collection Block Heel Square Toe Ankle Boots
Now 79% Off
Cons
- synthetic material may get sweaty
Between the icy pale blue hue, fancy faux croc texture, slightly flared block heel, and square toe, it’s basically impossible to pick a fave feature about this pair. BTW, they’re also on sale!
Cons
- may stain easily
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. Love the knit detailing and monochrome laces and soles, too.
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these waterproof warriors
Vionic Sienna Leather Ankle Boot
these waterproof warriors
Vionic Sienna Leather Ankle Boot
Cons
- soles can get slippery
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: “Love these Vionic boots! I purchased a size 10 so I had some ‘sock room.’ I needed short boots, and these fit the bill completely. Going to buy another pair because I love them so much!”
these cozy glove boots
Everlane The High-Ankle ReKnit Glove Boot
these cozy glove boots
Everlane The High-Ankle ReKnit Glove Boot
Cons
- may stretch out
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!”
Cons
- narrow toe box
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 these come in tan and brown, too.
Rave Review: “These boots are beautiful and very comfortable. I can go shopping in these boots and my feet do not hurt. I do not wear any shoes that hurt my feet. I bought a pair for my daughter, and she loves this style, too!”
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Cons
- may scuff easily
Um, these gorge iridescent pointed-toe leather booties are basically statement jewelry for your feet, thanks to their glowy, pearly uppers–and, of course, those killer gold chain-shaped heels. 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.
Cons
- pointy toes may pinch wider feet
Shine like the star you are in these rich auburn-hued suede stunners. Check out that modified, short cowboy boot-esque shape, not to mention the elegant seams and angled chunky heels.
Cons
- a bit of a splurge!
How striking are these made to order beauties?! They’re crafted from vibrant, textured Aso Oke cotton weave in a beautiful striped pattern, with Nigerian goatskin leather insole and lining for buttery-soft comfort.
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these checkerboard cuties
Tommy Jeans Leather Checkerboard Chelsea Boots
these checkerboard cuties
Tommy Jeans Leather Checkerboard Chelsea Boots
Now 56% Off
Cons
- elastic insets may stretch out
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 into. Oh, did we mention they’re on major sale, too? Pair these showstoppers with a mini skirt or fitted jeans, and you’ll be the coolest cat in the room.
these suede stunners
rag & bone ICONS Rover Chelsea Boot
these suede stunners
rag & bone ICONS Rover Chelsea Boot
Now 57% Off
Cons
- only comes in neutral hues
How sleek and chic are these suede Chelsea boots? We’re loving that softly pointed toe shape and stacked heel. And if this warm chestnut hue isn’t speaking to you, these come in a pale grey, classic black, or a darker brown espresso shade, too.
Rave Review: “These are the absolute perfect Chelsea boot and this color goes with everything! I have a few pairs of rag and bone booties now, and they are definitely worth the price. True to size, even with socks.”
these covetable cuties
UGG x Telfar Logo Mini Lamb Shearling Snow Boots
these covetable cuties
UGG x Telfar Logo Mini Lamb Shearling Snow Boots
Cons
- minimal footbed support
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.
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these waterproof wonders
Blondo Salome Waterproof Bootie in Taupe Suede
these waterproof wonders
Blondo Salome Waterproof Bootie in Taupe Suede
Now 70% Off
Cons
- need to break ’em in
We’re loving this 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.”
Cons
- an investment
If the perfect vintage ribbed leather couch were a pair of shoes, they’d be these stylish, comfy boots. Ethically produced in Peru using buttery Italian leather–yup, including the inside (lining), even–these have a carved wooden platform heel for some cushion between the ball of the foot and the ground. Plus, unlike many clog and clog boots out there, these are constructed sans staples, so they’re sleek and snag-free.
these shearling darlings
Coach Restored Leona Boot
these shearling darlings
Coach Restored Leona Boot
Cons
- limited availability
We’re all about that shearling, dahhling. The chunky lug sole and zipper-detailed vamp make such a great contrast. They’re sustainable, too: these gently used kicks have been restored to basically-brand-new condition through the Coach Repair Workshop, and cost a fraction of their original price. Reducing waste, having a second shot at scoring a hard-to-find style, and saving some cash? Winning all around.
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Cons
- may need to be broken in
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.
Rave Review: “I purchased these for a vacation where I expected a lot of rain. I normally wear a size 7 1/2 wide, but I sized up in these to an eight. I love the color: it’s a very, soft, warm, beige. They look very stylish on. Because of the light color, I immediately sprayed them with Scotchgard just in case. I wore them all day today in rainy weather to break them in and they have no wet splotches on them and still looks new! They were very comfortable, too. I wore them with regular-weight socks. I did put moleskin on my heels just to make sure they didn’t blister, but I probably didn’t need to. They were a little tight on my big toes, but not uncomfortably so. Felt very good to walk in. “
these lumberjack-chic shoes
Blondo Dyme Waterproof Ankle Boot
these lumberjack-chic shoes
Blondo Dyme Waterproof Ankle Boot
Cons
- runs small
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. Reviewers rave about the Goldilocks-like boot shaft height (not too tall or short) and polished yet simple look.
Rave Review:
“Loving these. Just wore them for a week when travelling and on my feet most of the day. I found them super comfy and easy to wear and I have plantar fasciitis. Tested in a drizzle but not in snow or heavy rain yet. Quality leather and sole. But definitely size up. I typically wear a 10 and the 11 fit me.”
these luxe teal ones
J.J. Gray Peter Military Boot
these luxe teal ones
J.J. Gray Peter Military Boot
Cons
- pricey
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.
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How we choose the most comfortable ankle boots:
How we choose the most comfortable ankle boots:
Cosmo’s fashion team—which includes Fashion Features Director Rachel Torgerson and Fashion Director Cassie Anderson, Fashion Editors: Tarah-Lynn Saint-Elien and Danielle Flum, and Senior Accessories Editor Andrea Zendejas—and have about 70 years (!!) 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 scour the internet to bring you a curation of the chicest options like it’s our job (because it is, heh).
We have pretty high standards when it comes to clothing and accessory recommendations. Each of our shopping articles adheres to the 15 Percent Pledge and includes products for all sizes. And you better believe we read those product reviews (and test many of the brands IRL) so you don’t have to. You’re welcome!
Fashion Editor
Tarah-Lynn Saint-Elien is the fashion editor at Cosmopolitan, writing weighty and witty stories that run the gamut of gushing over Zendaya to convincing you of everything you need in your closet! She began her journey in the industry with a fashion and faith blog and an internship at Elle.com almost 10 years ago. Since then, she’s also served as the style editor at The Haitian Times. The Haitian-American pageant queen is a Syracuse Masters graduate and the author of two books, including: Claim Your Crown. Follow her on Instagram and Twitter: @iamtarahlynn.
