To fashion girlies, fall/winter is widely considered the best sartorial season of them all. I mean, these months provide the perfect climate for maximum closet optimization. You can layer your favorite warm-weather clothes and turn them into cozy outfits, not to mention your entire jacket collection finally gets resurrected—nothing is off the table.
That said, the most joyous sartorial aspect of the season is fashion’s annual return to fall and winter boots. Chelsea boots, over-the-knee boots, ankle boots, and UGG boots are all styles we collectively go back to year after year. Beloved for their wearability and innate statement-making capabilities, these shoes are considered the GOATs every fall and winter.
As always, these staples will make their return, but this year there are several new styles on the menu, as well. For one, biker boots are back, waking up from a 10-year slumber to take center stage once more. The classic riding boot, too, is having a resurgence, offering a modern take on the 2010 Pinterest aesthetics of yore. Meanwhile, cowboy boots have become a must-have style that no shoe collection is complete without.
This is all to say: there are a whole lot of iterations to choose from. And now that the new year is here, it’s time to refresh and refine your personal collection. Ahead, I invite you to peruse these and more types of stylish boots.
Platform boots
Platform boots are the bad bitch’s best friend. They’re innately edgy, punk, and surprisingly functional, due to the added traction of the chunky sole (I wear mine instead of snow boots). Knee-highs, ankle boots, even over-the-knee—no shoe style can’t be improved with a flatform sole.
Try these:
ASOS DESIGN Carmen Chunky Flat Knee Boots
Steve Madden BERKLEIGH BLACK
Jessica Simpson Ulalie Platform Bootie
Now 25% Off
Camper BCN Black Leather Chelsea Boots
Now 20% Off
Cowboy Boots
Beyoncé didn’t technically invent these, but she might as well have. C’mon, Cowboy Carter? That plus the coastal cowgirl trend… It’s safe to say Western-inspired footwear has taken over the fashion scene. Typically, these are made of durable leather, with intricate and ornate embossing and embroidery. Pointed-toe styles are the most popular, but you can shop square toes, as well.
Try these:
Tecovas The Annie Star
Ariat Heritage R Toe StretchFit Western Boot
Charles Keith Cowboy Platform Knee-High Boots – Dark Brown
Jeffrey Campbell Dagget Western Boots
UGG Boots
Ok, this is a brand name and not technically a shoe style, but UGG has more than earned its place on this list. It made the padded, round-toe shoe style famous and now, it’s utterly ubiquitous. Usually, these boots are lined with thick fur and have a suede outer, for optimum insulation and comfort.
Try these:
UGG Women’s Classic Chillapeak
UGG Classic New Heights Genuine Shearling Cuffable Boot
Now 50% Off
UGG Women’s Classic Tall TrailGazer
UGG All Gender Classic Mini Pumped Molded
Knee-High Boots
Knee-high boots are really in their main character era. These are one of (if not the) trendiest boot designs of the moment, having successfully climbed the fashion ranks until they reached complete market domination. You can shop them in every fabric imaginable, from leather and suede to snakeskin, leopard print, croc, and more.
Try these:
Marc Fisher Lalita Foldover Dress Boot
Kenneth Cole Utah Pointed Toe Knee High Boot
Now 40% Off
Stuart Weitzman Xcurve 85MM Textured Slouch Knee High Boots
Nine West Rhoreee Knee High Boot in Silver
Now 50% Off
Combat Boots
Combat boots are basically the chill older sister of the pop-punk platform. Inspired by OG military boots, these feature a lace-up front and a rounded toe—usually made of black leather. They pair well with girly dresses and mini-skirts.
Try these:
Vivaia Round-Toe Lug Sole Lace-Up Ankle Boots (Florence)
Sam Edelman Elliot Combat Boot
Sinclair Faux Fur Lined Buttero Platform Boots
Now 30% Off
Reformation Ada Combat Boot
Now 50% Off
Biker Boots
Though biker boots—otherwise known as motorcycle boots—have been a staple in the motorcycle enthusiast crowd for, well, ever, they’ve also been the subject of interest among fashion girlies for a while now. You can spot a moto boot because of its rounded toe and buckled detailing.
Try these:
Aerosoles Comfortable Women’s Knee High Squared Toe Engineer Boot
Bullboxer Cora Motorcycle Boot
Now 56% Off
Steve Madden ROCKY Distressed Boots
TEAIEUI Women’s Knee High Boots Square Toe
Mid-Calf Boots
Mid-calf boot styles are equal parts chic and practical. Because of their casual-cool design, these might be the most versatile options on the list. You can wear them with pretty much anything, during pretty much any season.
Try these:
Sarto Amari Mid Calf Boot
Now 55% Off
Quince Italian Leather Riding Boots
Now 50% Off
madewell The Dimes Kitten-Heel Knee Boot
Now 19% Off
Free People Blaze Pull-On Boots
Chelsea Boots
Chelsea boots are a stylish unisex shoe style beloved by all. They usually hit at mid-calf or ankle height and are typically categorized by the stretchy panel on each side of the shoe. Said panel acts as a chic design detail and also makes for easy slip-on.
Try these:
Madewell The Idris Ankle Boot
AZALEA WANG Heartthrob Water Resistant Faux Fur Chelsea Boot
Sam Edelman Laguna Weatherproof Boot
Tecovas The Taylor
Riding Boots
Equestrians did it first! But now that the horse girl aesthetic is here to stay, as are these knee-high flat boots. Though they were originally created for *actual* horseback riding, they look just as good on the subway.
Try these:
NATURALIZER Jessie Knee High Riding Boot
Free People Emerson Equestrian Boots
Everlane The Riding Boot
Now 60% Off
Ankle Boots
Ankle booties are the mini skirt’s best friend. The two go hand-in-hand, working together to show off every inch of those legs. Designs run the gamut, from olive green stilettos to chunky lug-sole styles—Chelsea boots, too, are considered ankle boots, ICYWW.
Try these:
Mix No. 6 Tasea Bootie
Ann Taylor Ankle Chain Croco Bootie
Now 15% Off
MANGO Leather pointed ankle boots
Franco Sarto Alberta Bootie
Now 40% Off
Over-the-Knee Boots
Easily the most statement-making boot type on the list, these babies are bold by definition—and only for the brave of heart. Solid-colored styles are the easiest to style, but you can choose from heeled versions, flat, or platform, if you’re really feeling feisty.
Try these:
Jeffrey Campbell Overlook Over The Knee Boots
Stuart Weitzman ALINA CITY BOOT
Now 70% Off
Kelsi Dagger Brooklyn Logan Over-The-Knee Boots
Schutz Ashlee Mid Over The Knee Boot
Why trust Cosmo:
Cosmo’s team of fashion experts—which includes senior director of commerce Rachel Torgerson, senior accessories editor Andrea Zendejas, and fashion editor Danielle Flum—have decades of 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 to bring you the best clothing and accessory picks for every season. Basically, we’ve curated a chic little corner of the internet for you like it’s our job (because it is, heh).
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Kelsey (she/her) is a freelance digital fashion editor and writer with a knack for turning top-performing content into top-selling content. She has extensive experience in editorial and e-commerce strategy, having worked in both divisions during her years at Seventeen and Bustle. With more than a decade of experience in digital media, she also offers creative and social media consulting, as well as copywriting services. She enjoys cheeseburgers, traveling, and vintage hauls. Follow her on Instagram at @klstieg.
Megan Uy is an associate shopping editor at Cosmopolitan, where she searches for the best products in all things fashion, home, beauty, sex, gifts, and more, so you don’t have to. When she’s not writing for the site, she’s whipping up some cool and trendy content for the fashion section of the print magazine. She’s been with the brand since 2019 (when she was an itty-bitty editorial fellow), and she’s also written for Delish, House Beautiful, and People. Follow her on Instagram to get some BTS of the editor life and chaotic NYC content. Also, feel free to hit her up if you ever wanna discuss the madness that is TikTok.
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