26 Cute Winter Boots That Take Cozy to the Next Level

The only thing better than having a classic pair of Dr. Martens is having a faux-fur-lined pair with hiking-inspired hardware. Plus, the laces give the classic silhouette a pinch of personality. Pair these boots with a statement beanie, a warm jacket, and your favorite denims. Winter doesn't stand a chance!

Pros: Durable, rugged leather + insulated lining

Cons: Snug fit + not anti-slip

Another hybrid sneaker-boot moment! But this time it's in a classic Vans silhouette. A great way to step up your swagger. Maybe the best part about this boot is that you can style it as you would any pair of Vans and it's sure to elevate your whole look.

Pros: All-terrain traction + impenetrable sole to guard against leaks

Cons: Runs super-small, be sure to size up

Dua Lipa and Blackpink’s Lisa couldn’t get enough of Moon Boots earlier this year, and Moon Boots have been making waves amid the Y2K revival, not to mention dominating on TikTok. Thanks to the nylon upper and rubber sole, these boots are now pretty much synonymous with winter. You don't want to be caught without a pair.

Pros: Suction pads for ground control + available in many colors

Cons: Not the easiest to style

The tall platform boot has been going strong for a few seasons. Now, as we transition into winter, they're about to become even more relevant. The best part, though, is the style evolution of these beauts! Rather than just a trench and jeans, these are now a go-to for styling with skirts, dresses, and oversize looks.

Pros: The height provides extra leg warmth

Cons: A bit difficult to take off

Searching for an option that balances comfort and style? Puma’s Mayze Stack Chelsea Boots might be exactly what you’re looking for. An immediate attention-grabber with a supersized rubber sole and elevated leather upper, it's the perfect boot to pair with a down jacket.

Pros: Eco-friendly + a height booster

Cons: Heavy + not the easiest to break in

Add a touch of playfulness to your winter wardrobe with these lightweight, furry beauties. They come in just about every color, are warm, comfortable, and on-trend. Pair them with thick socks and a fun pair of tights.

Pros: On-trend + warm

Cons: Not a very durable sole (shallow)

These suede-and-shearling trim boots are true showstoppers. Given the moccasin-style lace detailing and the material, what’s not to love? And shearling never fails to channel classic winter style. This season is one of the best to let your footwear do the talking.

Pros: Cushioned foot bed for comfort + easy on/off

Cons: Bulky design + run small

Bella Hadid and millions more on the internet have been going crazy for UGG’s Mini Platform boots. The clear design is always a good time because your socks define the energy whenever you wear these boots. A “clear” classic that is a go-to pick for any cold, rainy, lazy day.

Pros: Cleans easily + slide on and off

Cons: Not ideal for snowstorms

Knee-high boots have long been making the rounds on streets and runways. It's no surprise that they continue to reign — but, here, not in the traditional sense. These knee-high cowboy boots are right at the intersection of comfy and cute. No, it's not the ideal boot for a wet day, but for those just-plain freezing days, let's give 'em a show. ;)

Pros: Pair effortlessly with jeans, denim skirts, and leggings

Cons: Not much traction

I'm sorry, but nothing screams “I'm a baddie and I know it!” more than a biker boot. Not sure if it's the hardware or — yeah, it's the hardware. They're like a pierced version of your typical tall winter boot. Not to mention: utilitarian leather straps! It's like wearing a superior form of boot.

Pros: Flexible technical sole made of latex foam for comfort

Cons: Not the warmest of boots

I can't be the only one who has found true love at Target — just about any and everything you need is there. Now, just in time for this next seasonal transition, these beauties are available for just under $50. Wear them with a comfy long dress or a skirt with an oversize cardigan.

Pros: Memory foam insole + faux leather

Cons: Snug fit, size up to wear with thick socks

A knitted dress or oversize sweater paired with over-the-knee boots is a foolproof formula for easy winter dressing, so incorporate a pair of these into your winter stylebook and try the winning combination. Plus, we can't get enough of the thick-lug sole design.

Pros: Recycled rubber + good for extreme conditions

Cons: Only available in black

Take your day-to-day style up a notch with these smart, almond-shaped-toe boots. They come in three color ways and the stacked block heel makes them comfy and safe for all-day wear. Also, where else have you ever seen a croc-leather Chelsea boot?

Pros: Sturdy + fit the ankle perfectly

Cons: Fit larger, be sure to size down

Sleek and refined, these patent calf boots are the ideal balance between fashion and comfort. An added perk? You can find them in three color ways — and if you do add them to your shopping cart, you’ll be sharing style with brand ambassador ITZY.

Pros: Height without sacrificing comfort

Cons: Can fit a bit narrow

Much like the tall platform boat, this Hunter commando boot has also had quite the style evolution. Unlike a typical commando boot, this one comes in a lighter, softer color way with a glitter accent — truly a win for winter footwear.

Pros: Padded collar + waterproof/certified vegan

Cons: Snug fit

Got my boots on but they look like sneakers! Can't get enough of this silhouette. It's a great alternative when you're off to tackle the winter but in less traditional footwear. The Kinetic™ RNEGD Sport design is the perfect balance between boot and sneaker. Plus, there are plenty of ways to dress this boot up or down.

Pros: Fully waterproof construction + insulated

Cons: Can cause discomfort after a few hours (not for all-day wear)

Looking for a season-appropriate replacement for your white sneakers? These lace-up, chunky boots by Lugz will do the job. The fur collar elevates the boot style while also providing extra comfort at the ankles. Be careful to wear these on a cold, dry day, rather than a rainy or snow day. And treat with care — they can get dirty pretty quick.

Pros: Flexastride memory foam footbed for comfort

Cons: Not easy to clean

Take your winter-footwear game to a new level with this water-repellent snow boot, featuring houndstooth detailing and a cozy lining. Love a boot that's technically impressive but with a nontechnical design. This three-inch block-heeled Franco Sarto design is perfect for date night during the cold months.

Pros: Available in multiple colors

Cons: Easy to spot-clean

We've recommended a few nontraditional winter boots that are stylish and comfortable, but these are a bit different because, yes, they are stylish and comfortable, but also nonslip! She's a functional winter wedge. Pair with fun tights and chunky socks to add dimension to your look.

Pros: Slip-resistant sole + arch support

Cons: Run small, be sure to size up

It's not often that Sperry, famous for boat shoes, comes up in a conversation about winter boots, but the brand's collaboration with Who What Wear is absolutely worth discussing. Most of our boot options are strapped or laced, but Sperry put a zipper on this boot, which immediately caught our attention. One of the most trend-forward boots of the season.

Pros: Lightweight and protective waterproof shell

Cons: Limited edition

Looks like a slip-on, sort of doubles as a boot. A low, ankle-height, clog-esque boot… Tasman and Ugg collaborated to create a waterproof clog, complete with a removable wool sock. Nice for a day of light rain.

Pros: Coated with water repellant + two looks in one (removable sock)

Cons: The socks are beyond thick, your feet may sweat

You can conquer winter with no problem as long as you own a pair of these. For less than 50 bucks, rule the runway of life with a splash of color and a fun silhouette. Plus, they conveniently slip right on and off.

Pros: Trendy + lightweight

Cons: Not much foot support

Told you, we're carrying cowboy boots into the winter. But how cool is Jeffrey Campbell for designing a rubber cowboy boot for the season? And get this: This stylish PVC boot comes in seven colors, making the styling possibilities endless.

Pros: Edgy and on-trend

Cons: Run big

For milder winter days, you can't go wrong with knits. Case in point: This pair of knit slip-on boots will add the right touch of craftsmanship to any cozy outfit.

Pros: Sheepskin lining for warmth/comfort

Cons: No arch support