There’s a heck of a lot of gear you need to take on winter in style, from the right pair of socks to a rugged henley for layering to a stylish and warm jacket. These are areas that certainly aren’t to be overlooked, and the same can be said for the boots you throw on this winter. We talked just a few months ago on The Style Guide about the best men’s boots to buy for fall, and winter calls for similarly rugged, functional style — yet with a bit of twist. Your stylish winter boots need to be able to take on blustery winds and drifting snow, and you need to be able to navigate to and from work, your favorite bar and that holiday or New Year’s Eve party. Trust me, it’s a lot … that’s why I think you’re going to dig the rugged leather boots we’ve got on tap today, from the remarkable Mark Albert Traveler Boots to a classic pair of shearling boots from Rancourt & Co. If you think I missed any brands or styles, hit me up on Twitter or drop a line in the comments below, and if you want to see how I’m wearing my boots this winter, check out my Instagram. Happy shopping!
Disclosure: This post contains affiliate links, from which a small commission might be earned on purchases. All opinions are the author’s own. Thanks for supporting the brands that support The Style Guide!
#1. Huckberry x Original Chippewa 6-Inch Service Boot — $280
It’s no secret that I’m a big fan of Original Chippewa and the brand’s classic Service Boots, so the Huckberry x Original Chippewa 6-Inch Service Boot is a ready-made winner in my book. These exclusive Service Boots feature a Vibram sole and a Goodywear welt for extreme traction and durability, even in the snow — and they’ll look particularly great underneath some American-made denim. Yes indeed, the Huckberry x Original Chippewa 6-Inch Service Boot is that elusive pair that can take you all around town and through the snow, then right on into happy hour.
#2. Red Wing Merchant Boot in Ebony — $320
#3. Mark Albert Traveler Boots (Huckberry Exclusive) — $345
We mentioned the Mark Albert Traveler Boots earlier, and with good reason. The Traveler Boots are what some might call the perfect pair of boots — if you’re into rugged, classic style. These exceedingly stylish leather boots feature full-grain Horween leather, an oil-resisting Vibram sole and the sort of construction that avoids slips and slides on snowy ground. The Mark Albert Traveler Boots even feature USA-made laces for an added dash of quality construction. Wear them with navy corduroys and a tan herringbone blazer for a blend of rugged and tailored style.
#4. Blundstone Super 550 Boots — $157.98
Let’s combine the look of a slightly more rugged Chelsea boot with the functionality of a dependable pair of snow boots, and … boom! The Blundstone Super 550 Boots are what you might get. The Blundstone silhouette is definitely unique and a bit quirky for some folks, but there’s no denying the traction-ready outsole and the brand’s Poron XRD sole technology. The Super 550 Boots are certainly a little more casual, and thus weekend-ready — style the Blundstone Super 550 Boots with your favorite bomber jacket.
#5. Rancourt & Co. Shearling-Lined Dresden Boot — $310.98
Here’s your new favorite pair of winter boots — maybe, just maybe. The Shearling-Lined Dresden Boots from Rancourt & Co. pack a ton of winter-ready functionality into one pair of boots, from the shearling lining — of course — right down to the sturdy Lactae Hevea sole. The Dresden Boots feature plenty of warmth and style points, plus handsewn construction and that classic moc toe upper. That’s an old-school combo that makes these Rancourt & Co. boots perfect for wearing on the weekend with a classic crewneck sweater and a faded pair of dark blue denim.
#6. Taylor Stitch Cap Toe Moto Boot in Black Steerhide — $315
Taylor Stitch doesn’t misstep … seemingly ever, right? And that goes for when the brand puts its mind toward crafting a uniquely stylish pair of rugged men’s boots, too. Simply put, the Taylor Stitch Cap Toe Moto Boots are well worth your time and money. The Cap Toe Moto Boots are made with durable storm welt construction and feature rich black full-grain steerhide leather, and that’s not even where the good stuff ends — they come with a pair of waxed cotton laces and a pair of antique leather laces for a bit of versatile styling potential. However you end up wearing the Cap Toe Moto Boots, they’re going to treat you just fine.
#7. Hudson Shoes Fernie Boots — $240
For the fella who appreciates a bit of tailored winter style to go along with weather-ready dependability, might I recommend the Hudson Shoes Fernie Boots? The Fernie Boots have been a bit of a hot seller this season, so you’ll have to act now to snag a pair — but rest assured, you’re getting a rugged and refined pair of captoe brogue boots done up in handsome brown leather. They just might be the perfect pair of boots to wear with a suit, as a thick rubber sole will help you combat the winter weather.