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31 best winter boots for women in 2021

Put your best foot forward with these chic winter styles.
Illustration of a woman outside wearing Toms Kelsey Wedge Bootie, Dr. Martens Leonore Chelsea Boots and Everlane The Glove Boot
TODAY Illustration / Toms / Urban Outfitters / Everlane

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With winter comes frigid temperatures, snow and sleet, so a cute pair of flats just won’t cut it unless you want frozen ankles. But finding the perfect boots for colder weather can be about as easy as spotting a unicorn. They need to be that magical combination of perfect heel height, calf width and shaft height. And they need to be versatile, not treacherous during inclement weather — and ideally, comfortable. It’s a lot to ask out of a pair of boots.

But we found a bunch that rise to the challenge. Whether you want classic or trendy, we found winter boots at every calf and heel height that make sense for the season, for everything from the office to dinner out with friends. Scroll down for some of our favorite options.

Booties for women

Sam Edelman Packer Leather Ankle Boot

With a relaxed moto vibe, comfy low block heel and dual zippers, these easy booties check all the boxes for a casual, everyday shoe. They’re even available in a wide fit.

Journee Collection Vienna Combat Boot

Available in five colors, these refined, dressed up combat boots have lace-up detailing along with side zippers, so taking them off after a long day is a breeze. The low heel also makes all-day wear comfy.

Jeffrey Campbell Leather Chelsea Boot

Both sleek and sophisticated, these refined, square toe Chelsea boots will work with dresses, skirts, you name it.

Lucky Brand Lilye Boot

Available in two wardrobe staple colors: tan and black, these boots from Lucky Brand are cute, comfortable and killer with a pair of skinny jeans.

Grafton Boots

An ankle boot with a wedge and padded insole? These are heaven in terms of comfort, and the deep navy color — perfection.

Steve Madden Gale Chelsea Boot

One thing is clear: Lug soles are in this season. And the studded trim around the base makes these boots extra special.

Everlane The Glove Boot

This fits-like-a-glove boot has a cult following. Made from recycled plastic bottles, it features comfy, stretchy ribbed fabric and a walkable 2” heel.

Dr. Martens Leonore Chelsea Boots

Waterproof, shearling-lined and with a little edge — seriously, what more could you ask for out of a winter boot? These revisit '90s grunge and kick it up a notch.

Michael Michael Kors Lottie Booties

Go big or go home with these 3 1/2” heel booties. They come in two stylish shades — a taupe-y “birch” and rust-colored “luggage.”

BP Willa Pointy Toe Bootie

With a practical, sturdy rubber sole and elastic insets, this well-priced leather bootie is great for kickin’ it around town.

Toms Kelsey Wedge Bootie

Brush off the winter blahs with impossibly comfortable boots. Available in seven color combinations, these have high-rebound cushioning, so you’ll never want to take them off.

H&M Ankle Boots

If you need an excuse not to wear sweats and sneakers these days, these boots are it. They’re a lesson in subtle simplicity — with a side zip and square chisel toes — but they may still outshine the rest of your outfit.

Snake Effect Ankle Boot

These are the boots you wear when you want to be anything but safe with your fashion choices.

Mid-calf boots for women

Zara Split Leather Heeled Ankle Boots

OK, we get it, it can be hard to show off your amazing new shoes on Zoom, but these boots are so amazing you need to at least take them for a spin to the grocery store or pharmacy. In sleek khaki green suede with a 3” heel and flexible sole, you’ll be comfortable all day — even when running errands.

Vagabond Shoemakers Tara Tall Chelsea Boot

Chelsea boots are incredibly versatile, and these chunky platform sole numbers — available in black and white — are no exception. Think trendy, but accessible.

Lucky Brand Javieri Boot

With a 2 ½” stacked heel, these brown suede boots are both stylish and practical for wearing all day long.

Free People Dakota Heel Boot

For boots that will speak volumes about your sartorial choices, invest in these slouchy pull-ons with a vintage vibe.

Mango Square Toe Leather Ankle Boots

These white leather boots with a square toe will give you major street cred.

Sofft Aronna Bootie

A little bit country, a little bit rock ‘n roll: Keep feet warm and dry in these western-style slouch boots, available in black, taupe and brown snake print.

Kolby Black Leather Pointed Toe Boots

These boots will wow with an unexpected, cylindrical block heel and mixed media leather/suede construction.

Lulus My Generation Mid-Calf Boots

The perfect pick-me-up on a grey winter day? New boots, obviously. We love these square toe, vegan leather, easy zip boots. Reviewers also rave about how comfortable they are.

Knee-high boots for women

Nine West Gabal Heel Boots

The ideal dress-up, dress-down boot, these have a 3.5” block heel, so they’re the perfect balance of sensible and sexy. Reviewers comment that they work well with narrower calves. They're also available in five gorgeous suede colors, as well as in white leather.

Michael Michael Kors Bromley Stretch Back Riding Boot

This stepped-top riding boot with a low 1” heel and elasticized back will become the breakout star of your wardrobe. Quick fit note: These guys run small so order a half size up.

Faryl by Farylrobin Mavis

There’s nothing quite like the confidence you get from wearing boots you adore, and we’re pretty sure these will fit the bill. With a 2.5” heel and super-soft slouch, these boots scream laid-back cool.

Cole Haan Hallee Stretch Boot

With a leather upper and elasticized sides, these boots conform to fit calves of various sizes, and the stretch also makes them comfortable. Reviewers note, however, that these can be a bit tricky to get on and off.

Chinese Laundry Krafty Knee-High Boot

If you like a little height on your boots, these are for you. The pull-on style has a thick wrapped 3 2/5” leather heel, and they come in synthetic leather or suede in six colors.

Mango Leather Boots with Tall Leg

The perfect backdrop for these chic square toe suede boots? Tights or jeggings to show off the style’s artful slouch.

Nine West Maxim Heel Boot

These top-rated, pointy-toe boots come in an amazing thirteen colors. So whether you want basic black or something more daring — like a yellow snake print or pink crocodile print — you’ll have your pick. A note on size: Because of the small toe box, you may have to order up.

Easy Spirit Reverie Boot

Your street style should be practical, and that’s where these rubber-soled flat boots come in. Simplicity is the name of the game with a minimalist buckle and modest heel. To be sure they’ll be a good fit, measure your calf circumference and lower leg length height to be sure the shaft won’t be too wide or tall.

Calvin Klein Freeda Boot

With a more modest 2 ¼” heel hight and rubber sole, these are a sensible-yet-gorgeous choice for slick, snowy streets.

Boden Round Toe Stretch Boots

Warm up to winter with these stretchy, easy-to-walk-in suede boots with an almond toe. Reviewers love that the stretchy material works with narrower calves.

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