15 Boots That’ll Keeps Those Toes Toasty All Season Long

Best Winter Boots for Men

Boots That’ll Keeps Those Toes Toasty All Season Long

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With Additions by Geoff Nudelman.

Sometimes it feels like winter will never end. Sleet, snow, cold — it’s straight-up relentless (like a house guest that won’t take the hint). For city dwellers, guys who are forced to battle winter head-on in urban jungles, it’s even worse, particularly if your commute consists of dodging icy pools of wintery despair, wearing wool or similarly decked-out suits, and trying to hold on to just a stitch of dignity in your professional appearance. It’s a delicate limbo. 

RELATED: How to Break in Leather Red Wing Boots

It’s no small feat then when a man can transition from transit to tower with style, with his lower body dry and warm. Sure, galoshes cut it on mild days, and there are a lot of good ones that keep summer scarps clean and dry. A killer pair of winters, however, do much more. 

From wingtips to almost-too-warm snow kickers, they are as varied as the season for which they’re designed. Made to make bedfellows with your wool suits, selvedge denim or even snow pants when time comes to flee the city and make tracks in waist-deep powder.

The reality is that no one boot can do it all. While a ten-eyelet dress shoe will cover you for cold dry days, it will struggle when it snows. Leather soles were never made for that kind of work. Similarly, boots made to withstand the elements — no matter how elegantly conceived — are often-times too utilitarian in circumstances calling for something cleaner. Ultimately, finding a pair that suits your lifestyle is a lot like slacklining. Each forward step requires a lot of deliberation and intentionality to be done right.

Here we take a look across a spectrum of different winter boot options: some for office, others for play, and still more that can transition between both. For winter comes for us all. It’s best to be prepared for whatever it brings.


Best Everyday Boots


Ben Sherman Brent Plain Toe 

Ben Sherman Brent Plain Toe 

Ben Sherman doesn’t make the flashiest gear — and shoes are often secondary for them — but they do make some really great budget-minded shoes. These lace-ups ooze classic style with a good traction sole and come in at a price point where you won’t be upset if you’re wearing them when you get caught in a cold rain.
$79.99 at Amazon.com

Danner Trail 2650 GTX Mid

Danner Trail 2650 GTX Mid

If you’re any sort of boot enthusiast, you already know and love Danner. New for this winter is this hybrid boot, which would do well in light precip and cold conditions. It’s lightweight, but durable and includes that typical, high-level Danner performance. This is an ideal option for a cold-weather travel boot.
$180 at Danner.com

Fracap + AETHER Dolomite Boot

Fracap + AETHER Dolomite Boot

We were thinking about including these as a more heavy-duty fall boot, but once we got our hands on them, they definitely screamed “winter.” These collab boots are based on an Italian army design and come from the generational leather makers at Fracap. You’ve got all the performance that’s expected in a high-end boot with just enough Italian style to make this wearable to the office. It’s officially marketed as a hiking boot (which it would do well as), but we like it more in the city slush (as an excuse to wear it more often). 
$400 at AetherApparel.com


Best Hiking Boots for Winter


Bearpaw Yosemite Boot

Bearpaw Yosemite Boot

You’ve no doubt seen Bearpaw at your favorite sporting goods or department store (if you still go there) and that’s because they’re dependable and trusty. If you’re a casual hiker and don’t need more bells and whistles, something like the Yosemite is a great value and will support you just fine. Don’t go hiking mountains with this, but a few miles here and there? Go right ahead.
From 44.95 at Amazon.com

Vasque Coldspark Ultradry

Vasque Coldspark Ultradry

Speaking of value, let’s talk about this deal at Vasque right now. This is a waterproof, insulated, well-tractioned boot for under $150. Vasque has a history of delivering exceptional bang for your buck, ensuring many seasons of good hiking with a single pair. Check out their site to learn more about the variety of technology built into these sturdy boots. 
$139.99 at Vasque.com

Adidas Terrex AX3 Mid GORE-TEX

Adidas Terrex AX3 Mid GORE-TEX

Adidas’ outdoor collection is an interesting one as it integrates a certain streetwear, athletic panache into what are generally good hiking boots. While these aren’t meant for major rain or snowstorms, these will get through cold, damp days with no trouble at all. Water resistant upper, Continental rubber grip (yes, from the tire brand) and more all under $80.
From $71.75 at Amazon.com


Best Snow Boots


Lacrosse Aero Timber Top

Lacrosse Aero Timber Top

Lacrosse improves on that classic “duck boot” design with a suede upper and a nice rubber outsole. What we like is that this particular design is a bit less utility than the average snow boot and a bit more refined. 
$149.95 on Amazon.com

Sorel Caribou Boot

Sorel Caribou Boot

For the fashionable-first reputation that Sorels have, they make a really great winter boot. The Caribou is a pretty classic take in three different colors with a removable felt insulation layer. A vulcanized rubber shell and non-loading outsole rounds it out. 
From $115.95 on Amazon.com

Pajar Pummel Waterproof Insulated Boot

Pajar Pummel Waterproof Insulated Boot

The main thing to know here is that these boots are rated to -22 degrees Fahrenheit. If you’re at temps that cold, you’re either out of your mind or already have a pretty good idea of the gear you’ll need to survive in that chill. Or just maybe you’re finally going on that Arctic cruise. Yeah, these would be good for that too. 
From $94.97 at NordstromRack.com


Best Boots for Lounging


Lamo Kai Moccasin

Lamo Kai Moccasin

This is a pretty sleek, streamlined moccasin chukka with some solid traction built underneath. Lamo’s whole ethos is built on California comfort and these boots are certainly well within that calling. 
$78.99 at LamoFootwear.com

Glerups Boot

Glerups Boot

Glerups have established something of a cult following for having just all-around handsome, unisex boots with no add-ons and just enough style. The brand is headquartered and makes their products in New Hampshire, so you know these are built to deal with tough winters. We think they’d be right at home in more mild settings too.
$155 at Huckberry.com

Minnetonka Sheepskin Ankle Boots

Minnetonka Sheepskin Ankle Boots

When it comes to moccasins, Minnetonka is one of those instantly recognizable, gold standard brands. This particular model is about as cozy as it gets with a plush pile lining. If the walk from the couch to the fridge is just a little too chilly this morning, pop on a pair of these and warm your soles. 
$77.95 at Amazon.com


Best of the Rest


Palladium Pampa Hi Originale

Palladium Pampa Hi Originale

For one of the bigger brands, Palladium does a good job packing style, performance and durability into a reasonable price point. While you wouldn’t want to take these canvas boots out for a long hike, they’ll do just fine throughout the workday in cold, wet conditions. (A little bit of waterproofing starch on the canvas would make these even better). 
From $74.95 at Amazon.com

Wolverine 1000 Mile x Sword and Plough Boot 

Wolverine 1000 Mile x Sword and Plough Collaboration Boot 

Wolverine’s iconic 1000 Mile Boot is made better through this release with repurposed materials from Sword and Plough, a veteran-owned surplus brand. With that inspiration in mind, these are the business casual boots you can trust for a snowy commute. Beyond that, they’re just well-built, classically-styled shoes you can pair with any number of outfit options.
$385 at Wolverine.com

Aquatalia Vladimir Suede Boots

Aquatalia Vladimir Suede Boots

Let’s say money isn’t an option and you wanted to make a statement with your winter footwear.  If you’re lucky enough to be in that situation, consider this weatherproof suede, ankle-high boot from Italian brand Aquatalia. The brushed suede is gorgeous and you’re also getting superior hardware in a unique format. Plus, all materials are specially treated to be weatherproof, making them a perfect pair for rough winter days that still require an upscale style.
$595 at Aquatalia.com

So there you have it, 15 great options for winter boots across the footwear spectrum. This winter, don’t let any bad conditions get in your way. Pick out your favorite pair and get out there. 

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