Best men's winter boots for Canadian winters — how to stay warm in the extreme cold

Frequent Timberland wearers might find this boot to be familiar: the Icon 6" boots pay homage to the brand's inaugural lifestyle boots of 1973, blending retro aesthetics with modern functionality. This model features full-grain leather, a waterproof upper and 400 grams of synthetic PrimaLoft insulation, which keeps the feet warm and dry in all situations. What I like about them most is they deliver most of the perks of heavy-duty boots like the Bivy 2.0 — traction, warmth and durability, to name a few — without weighing nearly as much. Plus, they are one of those rare boots that, at a time, fit into city, country and mountainside aesthetics.

If you are just as concerned with form as with function, keep reading. The Glacier Trail Sneaker High sells at a premium because it's more than a high-performing winter boot: it's a style piece that's part of this year's northern lights-inspired collaboration between Canada Goose and fashion brand CONCEPTS. But inside its bulky platform, custom colourways and flashy laces hides an airtight construction. Its premium upper has a stretch collar for comfort, a waterproof central zipper, and a durable rubberized leather wrap. 

Inside, the lightweight midsole and TPU heel stabilizer enhance comfort and support, and an HDry membrane makes it 100 per cent waterproof. The outsole is durable and grippy, thanks to its multidirectional tread, and two sets of hydro-treated laces help to customize the fit. If you can stomach the price point, they are your ticket to staying warm and in style.

On is a relatively new player in the world of winter boots; and yet the Cloudalpine is an instant hit. They feel athletic: their light weight of 595g, their responsive CloudTec cushioning that allows for a fast push-off, and the plastic Speedboard plate in the midsole for energy return, team up to provide a bouncy and energetic hike. They are also grippy: the Missiongrip outsole with specialized lugs delivers no-slip traction on icy surfaces, while a fast lock system keeps comfort locked in. Even better: their protective mudguard and waterproof membrane make them ready for any weather. Plus, their stylish colourways are an unexpected bonus.

Unlike other products on this list, the TAFT Rome boot isn't for the backroads: their leather stains if they encounter too much water, and your toes won't be happy with you if you expose these kicks to too much cold. But they shine in social settings and are made to compliment any outfit for winter nights on the town. 

Crafted from premium Spanish full-grain leather, and built with re-soleable Blake Construction, they’re designed for long-lasting city wear. They come with a lace-up design that securely locks the foot, while the leather sole with rubber inserts offers added durability and grip. They will keep a careful wearer stylish in the most hostile climates for several seasons.

With a thick Ultrafoam liner, T-MAX HEAT insulation technology, and extreme cold protection down to -40°C, the Bivy 2.0 Boots by Helly Hansen are built for comfort, even in extreme cold. I will admit that it’s difficult to pull off their Ski-doo-style look anywhere that is not covered in snow, but they have no match in the dead of winter. They do more than just heat retention: their rubber outsole allows for safe walking on ice, and their HYPER-DRI tech prevents water from getting in.

Take the adjectives you associate with HOKA running shoes (light, breezy, soft), and throw them out the window. The Kaha 2 Frost is a beast of a boot that may not be as delicate as your cloud-like runners but is every bit as high-performing. 

Packed with 400g of insulation, reflective foil, and a waterproof Gore-Tex membrane, it keeps your feet warm and dry in conditions as cold as -30°C. Then, the Vibram Megagrip outsole with 5mm lugs delivers unbeatable traction, while the dual-density CMEVA midsole ensures cushioned comfort: it wouldn't be HOKA without it. This hiker's boot also features glove-friendly pull tabs, top-hook lacing for easy on-off, and a compression collar to seal out the elements.

These boots are thoroughly dad-optimized: champions in the yard, in the hockey rink and on the hill. Featuring a faux leather outsole, a classic lace-up closure, and a round toe, they combine a classic design with everyday practicality. The lug sole and flat chunky heel provide stability and grip, while the pull loop ensures easy on and off. Perfect for braving wet weather without sacrificing too much style, these boots are a boon for the everyday Canadian; and will keep you comfortable while errand running, Christmas decorating, and doing every winter hustle in between.

I hope the Albertans who endured minus-40 temperatures had access to these foot furnaces from Helly Hansen, as they are the heaviest-duty, warmest models on my list. The Lockdown winter boots, equipped with a waterproof rubber shell and leather shaft, are clearly designed to withstand frigid temperatures. But there is more here than meets the eye. They come with a removable, heat-moldable technical liner system that makes the boots cold-resistant to temperatures as frigid as minus 50. And sure, they are bulky and not easy to store, but despite their size, they are relatively easy to slip on and off thanks to their floppy pull loop and easily lockable lacing system.

Many parts of Canada have so far managed to avoid snowy conditions this winter; and for that, it has been a good year to rock designer boots without risking salt wounds on their soles. The Model 008 by TAFT 365 has often been my footwear of choice for running errands around Toronto, and they remain as shiny as they were when I took them out of the box. They have a distinguished wingtip pattern, a comfortably lined interior, and a handcrafted, two-toned calfskin and suede construction. They are more for city strolling than for snow shovelling, but their heavy-duty rubber outsole still gives them a bit of heft. It's a stylish complement to a heavy-duty snow shredder.

I am a sucker for Chelsea Boots; I wear them for date nights, work meetings and shovelling snow — sometimes all on the same day. This sleek pair by Jack Erwin, handcrafted in Portugal, should be more expensive than they are. They come with a full-grain calfskin upper, leather-lined interior, and a padded insole that comfortably hugs the feet. They also nail the subtle details; they have a Blake construction, meaning their outsole directly attaches to the insole with a chain stitch, and a stacked leather heel to avoid quick erosion (a must if you dig your boots in salt and snow every day). You could pay hundreds more for similar boots — this version is a steal.