The 23 Best Mens Boots to Wear for Winter 2020

We compiled the best footwear to survive the snowy season

When the snow starts to fall, the quality of your wardrobe gradually declines in tandem. Startlingly low temperatures mean that it's easy to sink into comfy clothes, forfeiting your business wares for business casual, at best.

The one spot that really suffers? Your feet. Salt is poured onto sidewalks en masse—perhaps the very worst thing for your nice dress shoes. And you definitely can't ruin those sneakers you spent a fortune on in the winter's slush and grime. Most importantly, you can't roll into the conference room wearing hiking boots. You're not an animal.

For boots that can easily transition from the slushy sidewalks to a stately boardroom, look no further. And you know what they say, confidence starts from the ground up.

1. Swims Motion Wingtip Boots

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Swims’ boots are both functional and fashion forward. The striking blue hue takes these from dull to dope.

Buy Now at Swims, $275

2. Cole Haan Raymond Grand Chukka Boots

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PSA: Most of Cole Haan’s shoes are waterproof. You can now rock a leather chukka to brave the snow, for a day at your desk and date night dinner after.

Buy Now at Amazon, $141.71

3. Grenson Andy Hiking Boots

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Far Fetch

The lug sole of this boot is the deciding factor in whether it can weather the weather. With a sole-height of 38 centimeters, you'll float above the slush, literally and figuratively.

Buy Now at FarFetch, $380

4. Born Pike Boot

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Born’s Pike Boot is the updated rain boot. Easily slipped on in the a.m., the leather is coated in a waterproof construction that will keep your paws dry.

Buy Now at Born, $50

5. OluKai Hualalai Boots

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The shmanchy part of this pair of boots is the tweed insert. You'll feel right at home in this combination of leather and fabric and can undoubtedly walk tall through your office halls.

Buy Now at Amazon, $189.95

6. Dr. Martens 2976 Wintergrip


Ah, the classic Dr. Martens. They are grit– and salt–resistant, lined with warm fleece, and outfitted with a Wintergrip outsole. When wearing these, you can tromp through whatever precipitation comes your way and saunter into the office like a boss.

Buy Now at Zappos, $155

7. Dr. Martens 1460 W


The laced, big brother of the above, these Docs provide the same dependability as their relative. The shoe's upper and sole are heat-sealed and sewn together to ensure long-lasting wear. Also, they're hella cool.

Buy Now at Zappos, $150

8. UGG Hannen Waterproof Boot

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I know what you're thinking. UGGs aren't for the office. But these babies are sleek enough to peep out from your jeans or slacks at work. Lined in UGG's signature soft shearling, your toes will basically be napping all day while you crank. Naps at the bottom, crank up top.

Buy Now at Nordstrom, $230

9. Cole Haan Pinch Utility Waterproof Boot

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Cole Haan strikes again with an office-appropriate waterproof boot! The black colorway of this style offers flexibility in your wardrobe choices and can smarten up a cozy sweater day. I particularly love the chunky, lug sole.

Buy Now at Amazon, $88.38

10. Swims Motion Chukka Waterproof Boot

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It may seem impossible to wear a suede chukka in the snow, but Swims achieved the impossible. With a waterproof construction, you can have chic but dry comfort.

Buy Now at Nordstrom, $258

11. LL Bean Katahdin II

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LL Bean

The L.L. Bean Katahdin makes a great alternative to some of the more expensive dressy boots on the list. It’s cheaper than options like the Red Wing Iron Ranger and the Wolverine 1000 Mile, but is still a supremely high quality pair of boots built to last. The Katahdins utilize durable leather and a Vibram sole, making them a great option for extended wear, whether it be at work or for casual occasions.

Buy Now at LL Bean, $169

12. Red Wing Classic Moc

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Red Wing

This is one of the most iconic boots of all time, with good reason. You’d be hard pressed to find a more long-lasting pair of boots on the market, which makes these classic mocs a go to option for workwear or casual style. They’re heavy and structured, giving you the support you need to go about your business. They come with a pretty steep price tag, but they’re honestly worth it. This is a classic boot and a great fit for anyone who needs something for the slick winters.

Buy Now at Red Wing, $279.99

13. Red Wing Iron Ranger

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Red Wing

For those who want something a little more formal than the classic moc, this entry from Red Wing may just be the right choice. The Iron Rangers are great because they can be dressed up easily (they’ll look sleek with the right pair of slacks), but their structure and premium leather will keep them going in harsher conditions as well. The Iron Ranger is an American icon, enough said.

Buy Now at Red Wing, $329.99

14. Wolverine 1000 Mile

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These are pricey, but for the quality of the leather and the legacy of the brand, they may just be worth every penny. The leather is sourced from the 100+ year old brand, Horween Leather Co., and “more than 80 skilled shoemakers handcraft every pair in the U.S.A. with great attention to detail,” according to their website. The Wolverine 1000 Mile is a gorgeous, versatile boot; depending on your price range, these may be the right option.

Buy Now at Wolverine, $400

15. Blundstone Original Chelsea Boots

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Blundstone is a legacy brand. To this day, there still aren’t many brands who do Chelsea Boots better than the Australian juggernaut of laceless boots. Blundstone has been around since 1870; if you take one look at their boots, you’ll know why. Their Chelsea’s provide amazing shock absorption and feature their iconic pull tabs, allowing for an easier process of getting them on and off. They’re comfortable, durable and beautiful. What more could you want in your boot?

Buy Now at Blundstone, $189.95

16. Sorel Men’s Caribou Boots

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These are a little less traditionally stylish than some of the other options on the list, but they’re a great option for those who live in a place that experiences more extreme weather conditions. The waterproof boot from Sorel is immensely insulated, making them warm, comfortable and dry. They’re also kind of sick honestly; paired with the right pants, they could definitely be appropriate for a wide array of situations.

Buy Now at Sorel, $170

17. Men’s Basic Waterproof Timberlands

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The classic Tims need no introduction. Between the premium leather and commitment to construction, these waterproof Timberlands are a great option for casual wear, but can handle some harsher weather conditions as well. And from a style point of view, they’re still one of the most clouted boots on the market. These are probably the most-referenced boots in hip hop, so cop a pair for the vibes and stay cozy all winter.

Buy Now at Timberland, $168

18. Men’s L.L. Bean Boots

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LL Bean

L.L. Bean’s signature boot, sometimes referred to as the “Duck Boot” are a classic for a reason. The waterproof hi-top has been a staple of the brand since 1912, and not a lot has changed in their construction since their initial release. Although some might view them as goofy rain boots, they invoke a signature Northeastern kind of cool. We personally think they look great and make a great addition to a winter / rainy season wardrobe.

Buy Now at LL Bean, $139

19. Columbia Men's Bugaboot Plus III Omni Cold-Weather Boot

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Buy Now at Amazon, $129.95

This entry on the list is for those who really need a performance-oriented winter boot. They won’t exactly turn heads from a style perspective, but they’re minimal, durable and have incredible traction. These are a great option for anyone who needs a real winter boot, something that will perform under any conditions.

Buy Now at Amazon, $129.95

20. Kamik Men's Hunter Snow Boot

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This is another entry which is a bit more performance-focused. These Kamiks are a tried and true snow boot. I mean, just look at them; they’re entirely encased in a synthetic rubber. I’d like to see some snow try to get in.

Buy Now at Amazon, $57.95+

21. Danner Mountain Light

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Danner makes a beautiful pair of boots, there’s no way around it. The Mountain Lights are such a great combination of performance and style. They’re chunky and heavy, making them immensely supportive and immune to anything the world could throw at them. Simultaneously, the leather is beautiful and the craftsmanship can be easily recognized in person. They’re pricey, but every pair is built by hand in Portland, Oregon. You’re getting quality.

Buy Now at Danner, $380

22. Danner Arctic 600 Side-Zip

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This entry isn’t as stylish as the other Danners on the list, but these are an amazing option if you want to prioritize performance. They’re waterproof, warm and comfortable. The Arctic 600 also features a side-zip, making it much easier to put on than a lot of other boots with this many eyelets. What more could you want from a winter boot?

Buy Now at Danner, $165

23. Nike ACG Terra Antarktik GORE-TEX Black Midnight Turquoise

nike acg

Okay listen, we know these aren't technically boots. But they're just so fresh. As with all ACG (All Conditions Gear) products, their purpose is in the name: they're built for all conditions. We love a good sneaker-boot hybrid. If you do too, then these may just be the right choice. 

Buy Now at StockX, $124+
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