SHARP Finds: The Best Winter Boots of the Year

Now that the final leaves have hit the ground, we’re firmly in ‘frost warning’ territory across Canada. While fall-winter fashion gives us the gift of layering, it also means that sneakers and sandals don’t cut it. But, if we’ve gotta shovel the walkway, we’re going to do it with style. Plus, investing in a sleek pair of boots gives us one more reason to brave the winter winds. We’ve handpicked our favourites, from waterproof ankle boots to formal leather pairs to dashing combat kicks.

Dior Combat Ankle Men’s Boot

Dior Oblique Ankle boots
Learn More

Combat boots are a bit of a loaded term — the name evokes the costume-y quality of military fashion — but with this pair, Dior takes the style’s rugged, army edge to the luxury runway, with the polished look of refined leather. Aesthetically, we’d hardly call them a combat boot in traditional terms, but we’re still fond of the finished product. The collar is padded for comfort, making the soft insole all the better. Meanwhile, the dark Dior Olique jacquard puts a suave, sultry twist on the polished black calfskin. ($1,600)

ECCO Men’s Track 25 High Boot


1 of 2


2 of 2

Learn More

If you read the earlier version, you’ll know that we picked the ECCO Men’s Biom C Ankle Boot as a seasonal standout; so many of you shared the sentiment, however, that the pair sold out in days. Our condolences to those who shop on the weekends — it’s a dog-eat-dog world when you’ve got kicks like these up for grabs.

Luckily, however, the Biom C was just one of many boots we loved: ECCO is spoiled with clean-cuts, full-grain leather, and — in the case of the ECCO Men’s Track 25 High Boot — a waterproof layer to keep the rainy days from getting you down. It’s a pair of ankle boots that can scale salty winter streets and look good doing it. Oh, and there’s a bonus: thanks to a complex feat of engineering (the ECCO Comfort Fibre System™, if we’re naming names), these boots make sure that fresh air circulates inside, so you don’t have to think twice about wearing those thick holiday socks. ($340)

Timberland Premium 6-Inch Waterproof Men’s Boot (50th Anniversary Edition)

Timberland men's waterproof boots
Learn More

Even though fifty years is traditionally the golden anniversary, we’re going with this silver-grey pair of the iconic Timberland boot. They’ve got the tenacious spirit of top work boots, with a steel shank for arch support and sustainable insulation — 90% recycled material — so they’ll keep you plenty comfortable. Yet, with a heightened heel and sleek, premium-leather exterior, their durability comes in a stylish package. Did we mention they’re waterproof? ($200)

Prada Monolith Brushed Leather & Nylon Boots With Pouch

Men's Prada puch boots
Learn More

Slush is no match for the steampunk energy of these Prada men’s boots. The elevated heels swagger beneath slick onyx black laces and shiny silver buckle. It’s not just the style that makes a statement, either: the nylon leather pouch is an innovative, multifunctional step that emphasizes the pair’s bold look. ($2,200)

Hermes Fresh Ankle Boot

Hermes Fresh Ankle Boots
Learn More

Light, water-repellent fabric meets the soft warmth of a natural goatskin insole. Repeating H motifs line the perimeter of the honey rubber outsole. Oh, and last but not least: they come in five colours. But come on — that deep Hermes orange pops like nothing else. ($1,225)

HUGO Mixed-Material Half Boots With Rubberized Nubuck

Learn More

These dual-toned boots provide the best of both worlds: a blend of responsibly-sourced materials that don’t compromise on quality. The cow leather on the exterior, for instance, exclusively uses byproducts from the food industry. These Portugese-made boots sport an undeniable ease that makes short work of icy roads and hiking trails alike. ($328)

Fendi Silver Laminated Ankle Boots

Fendi Silver Laminated Ankle boots
Learn More

There’s more to the holidays than red and green — these ankle boots capture the chromatic glow of a silver bell. It’s a bold take on a classic figure, but there’s no better time of year to stand out from the crowd; when the sun sets before five, we could all use some extra shine. In truly forward-thinking fashion, this square-toed pair zips up from their F-embellished heel. ($2,190)

Louis Vuitton Discovery Ankle Boot

Louis Vuitton Men's Discovery Ankle Boots
Learn More

Despite their rugged look, the rubber soles of Louis Vuitton’s discovery boots are surprisingly lightweight. Their highly-technical construction provides a maximum grip on the streets, while the sporty design takes a cue from the playful authenticity of fresh powdered ski slopes. ($1,820)

Gucci Men’s Interlocking G Boot

Gucci Men's interlocking g Boots
Learn More

From the depths of its black leather construction to the gold sparkle of its interlocking G, this design has ‘classic’ down to a science. Sleek lines contour the silhouette with a nonchalant confidence, matching the comfortable luxe of the boots’ black patent leather. These G Boots bring black-tie suave to every occasion. ($1,620)

For more inspiration, here are our picks from last 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
Learn More

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. ($1,850)

Hugo Boss Suede Chelsea Boots

Hugo Boss Suede Chelsea boots
Learn More

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
Learn More

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. ($1,720)

Moncler Peter Boots

Moncler Peter Boots Black
Learn More

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
Learn More

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
Learn More

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
Learn More

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
Learn More

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
Learn More

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. ($1,570)

Jil Sander White Lace-Up Work Boots

Jil Sander White Lace-Up Work boots
Learn More

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)