The 25 Best Winter Boots for Men to Add to Their 2024 Rotation

• Category: Casual/work
• Waterproof: Yes
• Insulated: No
• Ankle height: Ankle
• Pros: Water-resistant, functional, durable, comfortable, versatile
• Cons: Could get dirty easily

Swims’ boots are known for being both functional and fashion forward. These simple but striking Charles Hybrid Water-Resistant Brogue Boots from SWIMS are technical in the sense that they are waterproof and made with leather/faux nylon material, have a solid rubber sole for traction, and features that make the boots comfortable such as the wing-tip round toe and comfortable insole. However, they are also a representation of simple style, and you can get quite a bit out of them styling wise due to their versatility. Priced at $328, you can get a lot of wear out of these boots.

• Category: Casual
• Waterproof: No
• Insulated: No
• Pros: Durable, Goodyear welted construction, hand stitched seams
• Cons: Not waterproof or lined, but they recommend sizing up (and you can wear cozy socks)

This entry from GH Bass is a perfect option for those who need something durable that is still formal enough for the office. For its price, GH Bass boasts the best quality available. The rubber midsole coupled with a Vibram lug outsole means the shoes will be soft and comfortable, with an extremely durable outsole to brave harsh conditions.

• Category: Casual
• Waterproof: Yes
• Insulated: No
• Pros: Waterproof, Vibram outsole, thick sole for comfort
• Cons: The chunky sole is a bit of a unique aesthetic for some

Comprised of smooth cow leather with a Vibram outsole, this entry from GH Bass is the ultimate option for waterproof shoes that don't sacrifice style. Weighing in at 402 grams, the shoes are fairly lightweight; the 1.57" heel coupled with the 1.18" thick sole means that the boots are elevated off the ground, and have a slight rocker for added comfort.

• Category: Casual/work
• Waterproof: Yes
• Insulated: No
• Pros: Offers half sizes, has a nice look, minimalistic, comfortable, breathable, Lightweight
• Cons: Isn't insulated

Born’s Pike Boot is what you would now call "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, has a lightweight EVA outsole centered around flexibility and traction, an extra layer of foam that provides additional comfort, and hones in on breathability due to its construction. Born also has this shoe available in half sizes, which is very helpful when it comes to boots as you don't have to worry about sizing up or down. Priced at $124, these are well worth every penny.

• Category: Casual
• Waterproof: Yes
• Insulated: No
• Pros: Water-resistant, has a good grip, multiple colors, has half sizes, is comfortable, durable
• Cons: May have to size down

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. Offering water-resistance, a good grip, three neutral colors that are easy to be paired with tons, and durability—it's hard not to say no to the Olukai's—especially at the $130 price point. You aren't spending too much, and in return you're getting a shoe that can last you ages. A win-win.

• Classic: Casual/work
• Waterproof: Yes
• Insulated: Yes
• Pros: Insulated, water-resistant, nice design, has a lug outsole, has an EVA midsole, comfortable, durable, flexible, affordable
• Cons: Limited sizing in certain colors

Ah, the classic Wolverine boots. They are grit– and salt–resistant, lined with warm fleece that will keep your feet toasty as you bare through the winter temperatures, and outfitted with a lug outsole. When wearing these, you can tromp through whatever precipitation comes your way in comfort thanks to the boots' EVA midsole and saunter into the office like the true boss you are. Showing off a great design and nice neutral colors, these $64 joints are almost too good to be true. Better snag them now before everyone else does!

• Category: Casual/winter activities
• Waterproof: Yes
• Insulated: Yes
• Pros: Has standard and wide sizing, breathable, has reflective lining, comfortable, lightweight
• Cons: Limited colors available

The laced, big brother of the above, these Omni-Heat Boots from Columbia provide the same dependability as their relative. The shoe's upper and sole are heat-sealed and sewn together to ensure long-lasting wear. Plus the shoes are built with reflecting lining and filled with 200g of insulation for additional warmth. The Techlite™ lightweight midsole gives yoou the appropriate amount of cushioning needed for superior comfort. Plus, they're also hella cool and stylish. Who doesn't want a hella cool and stylish pair of boots?

• Category: Casual
• Waterproof: Yes
• Insulated: Yes
• Pros: Insulated, waterproof, has rubber construction, comfortable, durable, versatile

I know what you're thinking. These boots aren't necessarily for the office (for some offices at least), but these babies are sleek enough to peep out from your jeans or slacks at work. Lined in  waterproof/breathable membrane and filled with 200g insulation, your toes will basically be napping all day while you crank. Naps at the bottom, crank up top. Even better, these boots boast a Insofit™ footbed for comfort, and a Multipitch Pro™ outsole that prevents any slippage and breakage.

• Category: Casual/work
• Waterproof: Yes
• Insulated: Yes
• Pros: Lightweight, durable, has good traction, works well for freezing temps, durable, versatile
• Cons: Only one color available

UGG strikes again with an possibly (emphasis on possibly) office-appropriate outdoor boot that if not for any place else, can work casually. Dressed in a wine colorway of this style offers flexibility in your wardrobe choices and can smarten up a cozy sweater day. The shoe is crafted with a leather upper and genuine shearling, and lined with 100% UGGpure wool lining/rubber sole, giving you genuine comfort and insulation. Not to mention, UGG says that apparently these boots keep you covered up to -20 degree celsius, which is pretty dang efficient if you ask us.

• Category: Casual/winter sports
• Waterproof: Yes
• Insulated: Yes
• Pros: Insulated, waterproof, nice design, comfortable, durable, flexible
• Cons: Could run big/small

With a waterproof construction, that offers chic but dry comfort, you'll be more than prepared to trek through the snow with these Thermo Snowdrift 2 Mid Waterproof Boots from Merrell. Featuring fleece lining, a recycled mesh footbed cover, and a recycled removable EVA foam footbed, you get the perfect mixture of functional and fashionable with these under $120 boots, as you can easily pair them with a range of winter pants, vests, jackets, and the whole nine yards. Affordable and with a hint couture is something that's hard to turn down.

• Category: Causal
• Waterproof: Yes
• Insulated: No
• Pros: Stylish, comfortable, affordable pricing, durable, versatile
• Cons: Could run big for some

Give us a Nike Air Force but make it a boot please! The Nike Lunar Force 1 Duckboot makes a great alternative to some of the more expensive dressy boots that are out there. Granted the Duck Boots cheaper than options like the Red Wing Iron Ranger and the Wolverine 1000 Mile, but it is still a supremely high quality pair of boots made with a durable leather that's built to last. The Duck Boots also utilize water-repellant features and lightweight cushioning along with a rubber sole, making them a great under $200 option for extended wear, whether it be at work or for casual occasions.

• Category: Casual
• Waterproof: Yes
• Insulated: No
• Pros: Great style, comfortable, weather-resistant, durable, versatile, strong outsole
• Cons: On the pricier side

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. Made with strong leather and traction, the boots are heavy and structured, giving you the support you need to go about your business. They come with a pretty steep price tag of $329, but honestly they’re worth it. This is a classic boot and a great fit for anyone who needs something for the slick winters.

• Category: Casual/work
• Waterproof: Yes
• Insulated: No
• Pros: Stylish, available in half sizes, offers a comfortable fit, has a vibram outsole, great construction
• Cons: On the pricier side

For those who want something a little more formal than the classic moc, this $350 entry from Todd Snyder 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. Then throw that in with the speed hooks, toe cap, and vibram outsole—again nuff said.

• Category: Casual/work
• Waterproof: Yes
• Insulated: No
• Pros: Well-crafted, durable, good quality, handmade, versatile, comfortable
• Cons: Could run narrow

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. The comfortability and breathable nature of the shoe is also a major selling point in our opinion as well.

• Category: Casual/work
• Waterproof: Yes
• Insulated: No
• Pros: Waterproof, has a TPU Outsole, has a cushioned midsole, has a comfort system and removable footbed, lightweight, comfortable
• Cons: Could get dirty easily

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 thanks to its maximum comfort system, cushioned midsole, and removable footbed, along with being durable and beautiful. What more could you want in your boot?

• Category: Casual
• Waterproof: Yes
• Insulated: Yes
• Pros: Weather-resistant, warm, comfortable, comes in half sizes, more than one color available
• Cons: May not fit everyone's style

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 made with waterproof nubuck leather, and 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. Priced at $199, you get a wide range of sizes present with the Sorel Men’s Caribou Boots and tons of comfort.

• Category: Casual
• Waterproof: Yes
• Insulated: Yes
• Pros: Classic style, durable, can last for years, has half sizes available, is versatile, given two width options
• Cons: Could run big/small

The classic Tims need no introduction. Between the premium leather and commitment to construction with its steel shank, 400g of insulation, and seam-sealed build, 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 $150 pair for the vibes and stay cozy all winter. This is one of the smartest choices you can make this winter.

• Category: Casual
• Waterproof: Yes
• Insulated: Yes
• Pros: Nice design, versatile, good for harsh weather conditions, comfortable, comes in different widths
• Cons: Could run small for some

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. Plus, L.L. Bean has added breathable GORE-TEX lining and warm insulation to these boots as well to increase the overall comfort level.

• Category: Casual/winter activities
• Waterproof: Yes
• Insulated: Yes
• Pros: Insulated, waterproof, more than one color available, comfortable, offers advanced traction, high quality, strong outsole
• Cons: Might actually run too warm

This entry on the list is for those who really need a performance-oriented winter boot, and it comes in the form of Columbia's Bugaboot Plus III Omni Cold-Weather Boot, which is water-resistant, insulated with 200g, and made with leather. They won’t exactly turn heads from a style perspective, but they’re minimal, durable and have incredible traction courtesy of Columbia's Omni-Grip™ Rubber. The built-in Techlite™ EVA midsole covers the cover the comfort component as well, making these under $120 boots a great option for anyone who needs a real winter boot, something that will perform under any conditions.

• Category: Casual/winter activities
• Waterproof: Yes
• Insulated: Yes
• Pros: Insulated, waterproof, available in more than one color, versatile, durable, offers great traction, comfortable
• Cons: Doesn't have half sizes

This is another entry which is a bit more performance-focused when it comes to winter boots These waterproof Insulated Rubber Boots from Kamik are a tried and true snow boot full of stability with its synthetic rubber outsole and deep lugs. 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. With two colors to choose from and priced under $75, these are a great affordable option to consider.

• Category: Casual/work
• Waterproof: Yes
• Insulated: No
• Pros: Water-resistant, nice style, multiple colors to choose from, well-cushioned, comfortable, technical, durable
• Cons: Could be too heavy for some

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 due to its full-grain leather, Vibram Kletterlift outsoles, and GORE-TEX waterproof liners. 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 ($440), but every pair is built by hand in Portland, Oregon. You’re getting quality.

• Category: Casual/winter activity
• Waterproof: Yes
• Insulated: No
• Pros: Insulated, weather-resistant, technical, durable, versatile, comfortable
• Cons: On the pricier side

The Arctic 600 isn’t as stylish as the other Danner's on the list, but these are an amazing option if you want to prioritize performance as they are waterproof, comfortable, warm with 200g insulation 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?

• Category: Casual/winter activities
• Waterproof: No
• Insulated: No
• Pros: Nice look, hybrid style between sneakers and boots, comfortable, technical, durable
• Cons: Could run big/small

Okay listen, we know these aren't technically boots. But they're just so fresh and so clean. Made with leather, the GORE-TEX has plenty of cool features such as the Nike React foam for comfort, the hard rubber that wraps around your toes and heels for stability, the ankle cinch cord, and more. 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. 

• Category: Casual/winter activity
• Waterproof: Yes
• Insulated: Yes
• Pros: Sturdy construction, comfortable, good traction, affordable, lightweight, durable, versatile
• Cons: Could run too narrow

You can always count on The North Face to deliver the goods, and they do exactly that with their Chilkat V Lace Waterproof Boots. Sturdily made with suede and seam-sealed construction. The Chilkat is very much a technical boot with features like 200g for insulation, a molded waterproof TPU shell, a compression midsole, and more. Priced at $135, this updated Men’s Chilkat V Lace Waterproof Boots is lightweight, comfy, and a good closet staple.

• Category: Casual
• Waterproof: Yes
• Insulated: No
• Pros: Minimalistic sleek look, comfortable, versatile, durable, comes in half sizes
• Cons: Not insulated

And you can always go with another tried and true American classic of course. The Tommy Flag Logo Leather Casual Boot from Tommy Hilfiger is one that comes well-crafted in leather, and offers a padded footbed and rubber sole for comfort. The boots are simple—you aren't getting a lot as far as style and technicalities go, but you can never ever go wrong with a simple well-made black boot. If you're looking for one, this is the perfect buy for under $100.