Winter footwear must be part of your seasonal survival pack. Snow, sleet and subzero temps don’t care about your low profile sneaker rotation or the daily drivers you thrashed through spring and summer. It’s the leather boots, technical hikers and rain boots that will get you through the mess—not only keeping your feet dry and warm, but also one of the most important pieces of your Après-ski or SoHo-ready winter look.

Inspired by everything from mountain climbers to soldiers, the winter boot styles are as diverse as their origins. Reflected in material, construction and silhouette, almost all boots promise to age like fine leather—patina over cracks, character over wear. Explore our guide to the best boots and Grailed’s top picks for the season, ranging from Balenciaga Stompers and Rick Owens Bogun Boots to Our Legacy Camions and 424 Marathon Wrap Boots. No snow in the forecast? No problem—you can still get in on the action.

Different Types of Boots

Chelsea Boots
Slip-on. No fuss. Clean lines. Chelsea boots are the Swiss Army knife of footwear—ready for anything. Recent styles maintain the classic elastic gussets and ankle-length silhouette, recent styles explore squared toes, chunkier soles and mixed-material compositions. Lemaire, Our Legacy and Prada are the brands to watch for this season.

Leather Boots
Durable enough for a dive bar, yet sleek enough for a date. Season-agnostic, leather boots are the ultimate utility player—breaking in beautifully over time and pairing with everything from black denim to tailored trousers. But not all leather boots are created equal, and with so many options, there’s a ton of room to miss the mark. If you’re going for the pair, Guidi’s front and back zips or lace-ups are the gold standard. Close second? MA+.

Utility Boots
Boots that mean business—whether you’re ripping upstate on a motorcycle, tinkering under the hood, chopping wood or none of the above. Nobody’s keeping tabs. These styles are built to get stuff done—or at least make it look like you are. Our Legacy Engine Boots, 424 Marathon Wrap Boots, or Timberland 6inch boots (classic or even Veneda Carter’s collab) fit the script.

Suede Shearling Boots
Love it or hate it (and trust us, we’re still on the fence), but UGGs are back—bringing with them a wave of shearling boots, some unapologetically furry, others more subtle in their fluff factor. If warmth is the priority, shearling lined boots from Diemme, Prada, and Blundstone are no-brainers. But why stop at the lining? LOEWE’s Lago boots take it to the next level—UGGs on steroids with a full shearling upper, available in both wedge and pared-down silhouettes.

Cowboy Boots
Cowboy boots aren’t going anywhere this winter. Whether you’re channeling full cowboy or just a subtle nod to Western design, cowboy boots are a great way to round out your wardrobe. We recommend a square or round toe. Play with stitching, detailing, and materials to find the perfect balance between classic and modern—think distressed leather, bold embroidery, metal applications or even unexpected textures like suede or exotic skins.

Rain Boots and Rubber Boots
The rubber footwear trend is alive and well. This season embraces the bold, oversized and unconventional design of Balenciaga Excavators, Troopers, and Bulldozers; Bottega Veneta Puddle Boots; and knee-high Margiela Tabis. Functional? Sure. A flex? Probably.

The Best Designer Boots for Men

Louis Vuitton x Timberland 6-Inch Boots
The Timberland 6-Inch boot gets a luxury remix with Louis Vuitton’s monogram and elevated detailing. For other takes, Timberland’s collaborations with Veneda Carter and Supreme reinterpret the classic with clean design and cultural edge.

Balenciaga Strike, Stomper, and Alaska Boots
Balenciaga doesn’t hold back. Strike Boots bring utilitarian energy, Stomper Boots are dialed up for maximum impact, and Alaska Boots reimagine winterwear with UGG-inspired comfort in a high-fashion package.

Our Legacy Engine and Camion Boots
Our Legacy’s Engine Boots offer a new silhouette with rugged, utilitarian appeal, while the Camion Boots stick to the Swedish brand’s signature minimalist yet durable approach. Both feel timeless without trying too hard.

Rick Owens Bogun Boots
Rick Owens’ Bogun Boots make a statement in every form, from the Bogun Beatle to pull-on styles. Expect dramatic lines, substantial soles, and the brand’s signature take on brutalist luxury.

Carol Christian Poell Tornado Boots
Carol Christian Poell’s Tornado Boots are unmistakable. Known for their twisted zippers and artisanal leather construction, they’re more wearable sculpture than traditional footwear.

Dirk Bikkembergs Bungee Boots
Bungee cord lacing gives Dirk Bikkembergs’ boots a utilitarian-meets-futuristic edge. Designed to stand out, these boots balance bold design with functional durability.

Guidi Back Zip Boots
Guidi’s Back Zip Boots are pure craftsmanship—soft leather, understated design, and construction that only gets better with wear. Available in zips, lace-ups, and everything in between.

Maison Margiela Tabi Boots
Margiela’s split-toe Tabi Boots remain as polarizing as they are iconic. Love them or hate them, they’re one of the most recognizable designs in footwear, with clean lines and a bold edge.

Prada Brixxen Chelsea Boots
The Brixxen Chelsea Boots by Prada update a classic with thicker soles and subtle modern touches, bridging traditional design and contemporary practicality.

424 Marathon Wrap Boots
The 424 Marathon Wrap Boots play with layered textures and deconstructed lacing, making them a standout for anyone looking for something offbeat yet wearable.

ROA Andreas Boots
ROA Andreas Boots blend outdoor functionality with a sharp, urban silhouette. Built for the trail but styled for the street.

Shayne Oliver x UGG Armourite Greave and Sabaton Boots
Shayne Oliver’s UGG collab pushes boundaries. The Armourite Greave Boots are tall and dramatic, while the Sabaton Boots take the same energy into a low-top form.

Raf Simons x Adidas Bunny Boots
Raf Simons’ spin on vintage Bata Bunny Boots turns military utility into something fashion-forward, with the original serving as a more practical alternative.

Diemme Roccia Vet Boots
The Roccia Vet Boots by Diemme bring Italian craftsmanship to a hiking-inspired silhouette. Functional but polished enough for city wear.

Visvim T.W.O. Boots
Visvim’s T.W.O. Boots reinterpret Western and workwear influences with meticulous Japanese craftsmanship, designed to age beautifully over time.

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