Winter Boots for Women That Don’t Suck

Trying to find stylish winter boots has always been the impossible task. But I love a good challenge—and when a bunch of my followers asked me to do a post on cute winter boots for women, I decided it was GAME ON.

Whether you’re wearing black jeans, classic denim, or leather leggings, Below, you’ll find a boot choice for every outfit.

I’ve included waterproof boots, shearling-lined boots, winter boots with a heel, and even boots that are on sale. You’re welcome!

I searched LONG AND HARD for the cutest winter boots on the internet, so I assure you, these are the best of what’s out there. Happy shopping.

P.S. These don’t technically fall under “winter boots,” but I just want to point out that Stuart Weitzman 5050’s are the greatest boots of all time. I love them so much, I wrote an entire essay about them, which you can read here.

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BEST SHEARLING & FUR-LINED BOOTS

GrandExpløre Genuine Shearling Trim Waterproof Hiker Boot, COLE HAAN

These Cole Haan boots were one of the most popular purchases among my readers last year. They’re insanely comfortable and wildly chic for a winter boot.

Women’s Ankle Boot, BEARPAW

The subtle wedge on this boot adds a few inches without looking clunky. Plus, reviewers can’t stop raving about how cozy these boots are!

Leonore Sherpa Chelsea Boots, DR. MARTENS

These faux-fur-lined booties keep feet nice and toasty without looking bulky or heavy. The sleek silhouette pairs perfectly with skinny jeans.

Samantha Hiker Boots, FRYE

The sherpa cuff on these boots adds an extra layer of warmth for especially frosty days. Frye boots tend to get better with age and use, so these are the perfect winter boot investment.

Joan of Arctic Boots, SOREL

These classic boots are made of waterproof leather, meaning they’re a tried-and-true winter boot that’s guaranteed to keep you warm and dry.

Izzie Genuine Shearling Lace-Up Boot, MARC FISHER LTD

With a chunky 1 and 1/2-inch heel, these boots are a fashion-forward take on the classic winter boot. I love the shearling detail on the front!

Joan of Arctic Next Lite, SOREL

A chicer take on the original Joan of Arctic, these booties pack the same comfort and protection as its predecessor while managing to come off as wildly fashion forward.

Vanetta Waterproof, COUGAR

This mid-calf, lace-up boot features a polar plush cuff and lining for extra comfort. I love the 1 and 1/2-inch platform that gives these booties a stylish twist.

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KNEE-HIGH WINTER BOOTS

Original Tour Packable Boot, HUNTER

Hunter boots are always a practical purchase—I still have mine that I bought years ago. I highly suggest getting these cute Cable Boot Socks from Hunter for the chilliest winter months.

Evie Wide Shaft Boot Waterproof, BLONDO

A ton of the #SilbSquad ladies were raving about Blondo boots in my Facebook group, so I had to check them out. I have to say, these are some of the chicest winter boots I’ve seen around (and I’ve seen a ton.)

Ruth, TUNDRA BOOTS

These cozy boots are perfect for braving the winter chill. I love the hidden side zipper for an easier on and off.

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WEDGE & HEELED BOOTS

Callie Lace-Up Boot, NATURALIZER

With a utilitarian-inspired silhouette, these lace-up boots are super versatile. The 3 and 1/2-inch heel adds height and elongates without sacrificing warmth and comfort.

Hurricane Waterproof Boot, JEFFREY CAMPBELL

The Chelsea-inspired detailing adds a timeless feel to this stylish boot, making it a must-have all season long. Plus, the waterproof fabric ensures that feet will stay dry in even the slushiest of snow.

Henderson Weatherproof Chelsea Boot, VINCE

I love this boot’s chunky 3-inch block heel—it adds an unexpected, fashion-forward spin on the classic Chelsea winter boot.

Liam Waterproof Bootie, BLONDO

If your looking for pair of boots with a shorter heel, these are the ones for you. The waterproof suede makes for a cute but casual boot that has garnered some rave reviews.

Elvina Waterproof Bootie, BLONDO

Could these black crocodile leather booties be any cuter?! I was seriously shocked when I learned these babies are waterproof. They’re the perfect lightweight, chic winter boot—I’m considering buying two!

Berry Mid, TROTTERS

My favorite thing about these boots? The slip-resistant rubber soles that make winter wipeouts a thing of the past. I’m also a big fan of the chic buckle detailing.

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BIKER & COMBAT BOOTS

Serena 8 Eye Boots, DR. MARTENS

Docs are classics for a reason—they’re simply that good. This pair is fleece-lined, making it perfect for those extra cold days.

Nanette Combat Boots, GRENSON

From the subtle sherpa detailing to the shiny leather, I seriously love everything about these boots. They’re definitely pricey, but you’ll get a ton of wear out of them—and how cute is that hardware?!

Surrey II Waterproof Boot, KODIAK

These boots feature a waterproof finish and warm insulation, making them a sturdy, practical pair of boots that are perfect for snowy days.

Rogue, KAMIK

These cozy winter boots are perfect for that winter trek to work. The herringbone collar adds a chic twist on the otherwise plain boots.

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