SHARP Finds: 10 Best Winter Boots of the Year

Although we’re trying to savour the last few weeks of fall — one thing is for certain: winter is coming – and with it comes mounds of snow, sludge, sleet, and lots of (very) slippery ice. But, fear not! It takes a good boot to make it through our infamous Canadian winters — a boot that keeps your toes warm, is comfortable, will protect against the unpredictable elements, and of course, make you look good. And we have just the one — well, the 10. Here are our favourite boots to have on hand ahead of the colder months.

Prada Monolith Brushed Leather Chelsea Boots

Prada Monolith Brushed Leather Chelsea boots
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Although the Chelsea boot has a long — and favourable — history, sometimes putting a modern spin on a classic is a recipe for success, as seen here with Prada’s brushed leather Chelsea boots. The chunky rubber lug tread sole gives added grip and a post-punk edge, while the brushed leather and elastic gusset provide a more polished finish. They’ll help you walk that fine line of fashion forward with a timeless twist. ($1,450)

Hugo Boss Suede Chelsea Boots

Hugo Boss Suede Chelsea boots
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Just because the weather is dark and gloomy, doesn’t mean your footwear has to be. Brighten up with Hugo Boss’s cleanly styled light beige suede Chelsea boots with seasonable pull loops and a contrasting welt. Whether opting to pair them with lighter earthy tones, or using to contrast against darker attire, there’s a surprising amount of versatility here. ($398)

Fendi Force Lace-Up Ankle Boots

Fendi Force Lace-Up Ankle Boots
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These Italian-made, black leather lace-up ankle boots have a zipper on the inside to make them more comfortable, and FF jacquard fabric details in grey and black for added flair — once again providing a perfect balance of style and comfort. Though similar in chunkiness to the Prada option above, somehow these soles manage to be a touch less obvious. ($1,590)

Moncler Peter Boots

Moncler Peter Boots Black
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The ideal match to your Moncler jacket — or equally impressive on their own — the Moncler ankle-high Peter boots in black will be your new cold weather go-to. Their intricate design, complete with a tonal bungee-style drawstring closure, is incredibly sleek yet subtle enough to be suitable for both the gent looking to get noticed and the one looking to blend in. ($1,090)

Timerbland Greenstride TBL Originals Ultra Waterproof Boots

Timerbland Greenstride TBL Originals Ultra Waterproof boots
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There’s a long list of remarkable features that these waterproof Timberland boots have but one of the most noteworthy is the built-in anti-fatigue technology which helps deliver all-day comfort and support to your feet for those long “on-the-go” days, with the use of a comfort system created with shock-absorbing, geometrical technology. Now try saying that five times fast. ($190)

Brunello Cucinelli Leather Boots

Brunello Cucinelli Leather boots brown
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For the guy who has a rugged edge but still likes things neat and refined, this one’s for you — because when it comes to Italian luxury, Brunello Cucinelli does it right, and these dark brown leather boots are no exception. The textured leather upper and lace-up vamp sit atop a lugged outsole providing optimum traction — as if they were specifically curated for the stylish man on the move. Pair with your favourite denim and you’re ready to take on the day. ($1,695)

Swims City Hiker II Waterproof Boots

Swims City Hiker II Waterproof boots
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When you’re picking up groceries, heading to the dog park, or just looking for something a little more casual, say hello to these hikers. Thanks to their durable lug soles and waterproof construction, these boots are up to any task. While their dark blue colour, orange detailing, and rugged exterior make a fashion statement, they also pass the functionality test as they promise to keep your feet dry and comfortable. ($395)

Ermenegildo Zegna Black Carlo Lace-Up boots

Ermenegildo Zegna Black Carlo Lace-Up boots
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Sometimes simplicity is key and these ankle-high grained leather boots in black are proof. Ermenegildo Zegna’s take on a classic hiker boot is exactly what you’d think: well built, superior functionality while still being subtly sleek and fashionable. With a classic rounded toe, lace-up closure, padded collar, and leather pull-loops, you simply can’t go wrong. ($1,300)

Bottega Veneta Black & Green Puddle Bomber Boots

Bottega Veneta Black & Green Puddle Bomber boots
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For the adventurous lad, literally, but also those with a bold fashion sense, there’s no better option than Bottega Veneta’s black and green puddle bomber boots. Ankle-high paneled nylon canvas meets a round rubber cap toe and lace-up green closure for the ultimate result: boots perfect for any trek. Get ready to make a statement everywhere you go. ($1,230)

Jil Sander White Lace-Up Work Boots

Jil Sander White Lace-Up Work boots
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Be prepared to blend in with the snow wearing these white, ankle-high, leather work boots — but trust us, you won’t blend in elsewhere. With these Jil Sander lace-ups, crafted with a tonal lace-up closure, round toe, embossed logo on the outer side, and finished with silver-tone hardware, you’ll surely turn heads. ($1,580)