22 Best Men's Winter Boots in 2020: Footwear to Handle the Wettest, Slushiest, Blizzard-iest Weather

22 Best Men’s Winter Boots in 2020: Footwear to Handle the Wettest, Slushiest, Blizzard-iest Weather


When your daily routine requires trudging through sleet and snow, you don’t want to wing it with sub-par footwear. You need the best men’s winter boots to stand up to the elements and prevail. We like a sleek, dressy boot—something you can wear in the winter, but have to be careful with to keep in good shape—as much as the next guy. More than the next guy, probably. Same goes for high-top sneakers, or a trusty pair of chukkas, or anything else that can (kind of) pinch hit for an all-weather shoe in the winter if you live somewhere mild. They’re all good. But there comes a time every winter when these pinch-hitters won’t do. You need to bring out the big guns.

Problem is, most boots with that kind of attitude and all-weather performance cred tend to leave a lot to be desired in the style department. That’s where these boots shine: durability at their core, with good looks as an added bonus. They’re like luxury SUVs for your feet, outfitted with the finest winter tires money can buy. Whether you need a pair for dominating the trails or the boardroom or shoveling your driveway, we’ve got the right all-weather winter boots for you. Here are our 22 favorite pairs for every budget, style, and need.


The Best Hip-Hop-Approved Winter Boots

Timberland 6-inch premium waterproof boot

Decades of rap videos might have convinced you that Timberland’s iconic six-inch work boots are a thing best kept box-fresh and pristine, steered clear of the elements altogether. But that’s doing your Timbs a massive disservice. Fact is, those nubuck uppers you’re being so precious about are fully waterproofed, lined with PrimaLoft insulation, and built to combat much more extreme conditions and strenuous environments than you probably ever encounter on a day-to-day basis. Spray ‘em down first if you must, give them a quick wipe every once in awhile, but don’t be afraid to treat them like the true-blue winter boots they are.

The Best Anytime, Anywhere Winter Boots

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Blundstone 500 Chelsea boots

We’ve sung the praises of Blundstones many, many times before. Here’s a quick recap, though, for the TL;DR crowd: Blunnies are comfier than that memory foam mattress you just bought through a podcast, impervious to wetness and chill, easy to slip on and off, and strangely, implausibly fashionable. If you’ve never owned a pair, this is the year to take the plunge—all the hype will make total sense the moment you slip them on.

The Best Practical Winter Boot

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Sorel Caribou winter boots

This is basically the Hummer of winter boots. The waterproof nubuck upper extends to your calf, giving you fuller protection for stepping through snowbanks and such, and it’s been sealed at the seams for greater weather resistance. And the duck boot-style rubber on the outer foot ensures that your socks will stay bone dry, no matter how wet and snowy the conditions are, while also giving the boot added grip around the footbed. And here’s the best part: the sherpa lining. It’s not real wool shearling, unfortunately, but Sorel’s synthetic stuff is still exceptionally warm and comfortable, cushioning your ankle as you slog your way through the backwoods, slush-covered city streets, or anywhere in between. And the whole sherpa-lined inner is removable and washable, so you can toss it in the washing machine once every couple weeks to keep it fresh throughout the season.

The Best Winter Hybrid Boot

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Diemme Balbi suede and rubber chelsea boot

If you still aren’t sure about duck boots, Diemme will change your mind with this slick hybrid. The Balbi has Chelsea-boot-like elasticated side panels and lush textured suede up top, with impenetrable, element-conquering rubber encasing the full length of your foot below. It’s kind of like a centaur for your feet, only there’s nothing mythical about it—aside from how Greek-godly the fits you’ll get off will be.

The Best Big-Ass Winter Boot

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Bottega Veneta Puddle rubber boots

The leather gurus at Bottega Veneta have wilded out in the boots department as of late (see: these absolute-unit chelseas), but we still didn’t see anything like these molded rubber beauts coming. They’re big honkin’ boots that land somewhere between Doug Funnie’s massive sneakers and the spray-on shoes from Cloudy With a Chance of Meatballs. Somehow, they not only work, but will look absolutely righteous with everything in your wardrobe through the winter and well into rainy season.

The Best Do-It-All Boot

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New Balance Tokyo Design Studio x Snow Peak Niobium shoe

New Balance has been on fire all year long, and this collab with Japanese outdoorswear savants Snow Peak is probably its crowning achievement. An all-in-one shoe sounds like the stuff of infomercials, but this feat of footwear engineering transforms from a sleek slip-on mule to a weatherproofed boot with a few quick zips. Whether you’re bracing for winter on the couch or toughing it out on foot, these modular marvels will get you through.

The Best Pamper-Yourself Boot

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They’re comfy, they’re warm, they’re what you deserve after 2020. Like Crocs and Birkenstocks before them, Ugg boots have gone through a gauntlet of lazy jokes and emerged on the other side as a certified classiqué. And before you protest that Uggs only look right on soccer moms, we’d remind you of their original purpose—keeping the toes of Australian big-wave surfers toasty on frigid early mornings—and also point you to these excellent shots of two opposite-spectrum style kings, Shia LaBeouf and Tom Brady, pulling them off with aplomb. They look cool, trust us. And even if they didn’t, it wouldn’t matter, because slipping on these shearling-lined, heat-regulating icons is the ultimate act of self-care. If you’ve never experienced the sheer physical pleasure of a day in Uggs, it’s time for that to change.


15 More Winter Boots We Like

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Salomon X Ultra Winter CS WP 2 boots

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L.L.Bean 10″ tumbled-leather shearling-lined Bean boots

Bean boots have a habit of selling out the way hot Nikes do, so we’d advise getting your mitts on this extra-cozy shearling version while you still can.

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Xtra Tuff 6″ Legacy Chelsea boot

As beefy as the name implies.

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Bogs classic high waterproof boot

If your winters are more rainy than icy, these neoprene-laden boots are for you.

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Dr. Martens Made in England Harris Tweed 1460 boots

A very English boot.

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Season Three “The Ansel” boot

Classic hikers with a few new tricks up its sleeves, like a pillowy orthotic insole, a Vibram outsole, and merino wool lining.

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Suicoke Bower Skull Target

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Roa Andreas hiking boot

Like if Air Jordan 10s had Vibram soles and were built for scaling mountains.

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Yuketen Angler leather-trimmed brushed-suede boots

Even boots have grown their hair out this year.

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Acne Studios Bertran tonal m hiker

The product description calls these “city-ready,” which is code for “not for actual hiking.” Fine by us, honestly.

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Viberg Pachena Bay boot

Old-world craftsmanship with a touch of modern-day Thinsulate insulation (and a rugged-as-hell lugged rubber sole).

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Thom Browne wingtip brogue grained-leather boots

If you say “suited and booted” three times in the bathroom mirror, these benchmade brogues appear.

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Baffin Wolf boots

Form is function.

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Danner Mountain Light boot

The hiking boot that begat all others.

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Arc’teryx Acrux AR GTX mountaineering boot

Darth-Vader-on-Hoth type beat.

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