The Best Winter Boots That Will Keep You Dry and Warm

Manitobah Mukluks are just one Indigenous-owned business to know and support because their products are well-made, durable and perfect for Canadian winters. These waterproof boots promise to be the warmest, most comfortable winter boots you’ll ever step into, and we can see why. These boots are breathable, and made of sheepskin shearling and natural material, insulated to keep your feet warm up to a whopping -32°C (temps that are no stranger to many regional winters). The flexible and durable sole promotes circulation and offers barefoot-like comfort.  Waterproof Snowy Owl, Manitoba Mukluks, $230 (On sale now).

Hunter boots have been around for more than 60 years for a reason; they’re not only cute and comfortable, but incredibly durable too. They can pair with so many outfits when you’re just out on the town, but this particular pair too is intended for colder climates, ensuring your toes stay warm in those cold Canadian winters. This Original Tall Rain Boot includes an insulated fleece lining and can be worn in temperatures that dip to as low as -5°C (though when coupled with warm socks, we’d argue in temps even colder than this). Each boot is made from natural vulcanized rubber, to ensure they’re fully waterproof. Plus, they're fully certified vegan.

Women's Tall Insulated Rain Boots, Hunter Boots, $220.

An option for those looking for a trendy (read: chunky) take on the classic Chelsea boot, PrettyLittleThing’s off-duty, round-toe off-shine Chunky Sole Ankle Boot will keep you above the winter slush and looking cute in the process. It has high-shine material and features synthetic lining and sock for easy pull on.

Black PU Round Toe High Shine Chunky Sole Ankle Boot, PrettyLittleThing, $132.

Love it or hate it, the UGGs are coming back with a vengeance and perhaps with reason. UGG boots reigned supreme even before our modern pandemic woes, where comfort often trumps style; Aussie ex-pat and surfer Brian Smith started the brand in 1978 before the style became a symbol of SoCal beach culture, gaining momentum in local surf shops along that coast. Some 30 years later, these UGGs casually combine both function and fashion, while delivering on the comfort the brand is known for. The boot is made of 100 per cent waterproof full-grain leather and wool and has a rubber sole.

UGG Australia Women's Kesey Motorcycle Boot, Amazon, $195.

Aldo’s Balaraen Chelsea boot is another great statement-making trendy option in a popping white to boot (see what we did there?). The modern silhouette's upper part of the shoe is leather, and the sole is rubber, ensuring you have enough of a barrier between you and the elements.

Balaraen Chelsea Boot, Aldo, $80 (On sale now).

It’s no secret that the classic cowboy boot is having a moment, and any boot roundup this season without at least one pair would be incomplete. While they do require some care and TLC (read: don’t go splashing in puddles with them), these Solow Western cowboy boots by Dolce Vita are worth the attention. A great statement piece to kick up any ol’ pair of jeans or dress, these old school western-style bad boys have a subtle tonal western stitching and have a block heel perfect for walking in. (Cue "These Boots are Made for Walkin.")

Solow Western Boot, Nordstrom, $144 (On sale now).

This fashion-forward take on the classic Sorel Joan Explorer boot comes in five colours and offers a cool, street-ready weather boot that’s water-resistant and warm. Featuring microfleece lining and faux-shearling trim, the boot also has a traction-ready rubber sole. The slight platform elevates the look of a traditional winter boot, giving you something to feel cute about.

Sorel Women's Explorer II Joan Cozy Boot, Amazon, $150 (On sale now).

Another cold-weather favourite, Roots made the Nordic Winter Boot to be waterproof, warm and not too bulky. It has a premium full grain leather shaft, a winter rubber shell and is insulated with a fleece liner to keep your feet warm and dry. It even comes with two sets of laces to mix-and-match your outfit. 

Nordic Winter Boot, Roots, $248.

These premium-quality suede boots come in a platform style, giving you that added boost in height without the hassle of making a heel work in sub-zero conditions. A twist on the classic, it has the fuzzy lining so once you slip into these comfy boots, you may never want to take them off. Just ask Bella Hadid and Elsa Hosk.

UGG Classic Mini Platform Boots, Amazon, $185.

This iconic Moon Boot certainly looks at-home down the slopes, but this statement-maker is also super practical for Canadian winters. Keeping you dry and warm when the snow squalls set in, this boot is the perfect go-to when you’re looking to look cute and stay practical.

Moon Boot, Farfetch, $213.

Perhaps less an every-day boot, than a dressier alternative for those nights out, this stunning croc-inspired high-knee boot with a pointed toe and kitten heel is at once classic and edgy.

Stevie Boot, Free People, $473.

Step up your fashion game with these attractive, soft butch beauties. Dr. Martens' Serena captures the classic doc — but offers faux-fur lining and a thick rubber sole that will help you counter even the toughest winter days. This boot is a great option that will also give you a very Winona Ryder vibe.

Serena Faux Fur Lined Lace Up Boots, Browns Shoes, $210 (On sale now).

Heavy-duty and heavily chic, these fleece-insulated short winter boots feature a lugged sole and an ortholite footbed. Keeping you warm and dry when that snow starts to pile up, these boots are a go-to for cold days and the ideal boot for enjoying the season due to the drawstring topline. Snowball fight, anyone?

Hunter Women's Original Insulated Snow Short Boot, Amazon, $149 (On sale now).

This rubber rain boot is not only stylish, it’s also waterproof with a lightweight sole and – wait for it – comes in a wide-calf option, which means there’s finally a tall boot option for those of us who have trouble squeezing into some of the more narrow styles. Win-win? We think yes!

Ilse Jacobson Rubber Boot, Nordstrom, $230.

When it comes to winter travels, packing the essentials is key. When your destination means added layers and the unpredictability of cold-season weather, this can be tricky. The footwear you pack should be practical and versatile enough that you can wear it for multiple activities, and durable enough to sustain in varying terrains and conditions. For a pair that travel light and will keep you warm, we love these. Shearling-lined, cozy and crafted with adventure in mind, these lightweight boots won’t weigh down your luggage. Now all you need is the destination!

UGG Classic Mini II, Nordstrom, $150.

This cute leather mid-calf boots from Amazon features fauxfur lining and a rubber outsole for personalized comfort. Functionality was taken into consideration when crafting these boots as they have a built-in pocket wallet made for keys, cash or maybe credit cards. Look and feel good this winter with this stylish pair.

Dream Pairs Women's Mid Calf Combat Riding Boots, Amazon, $86.

What could be cooler, or more practical for those winter rainy days, than a great pair of rubber rain boots? This style has never quite gone out of fashion, and every year, designers seem to up the bar with new variations on the classic. With more cold-weather features than ever, the new rain boot not only keeps you dry with innovative technology and materials, but also looks cooler than ever. We love the quilted-effect of these!

Women's Refined Slim Fit Adjustable Quilted Tall Rain Boots, Hunter, $235.

These black rubber boots may look more fashion than function, but don’t be fooled by their good looks, these beauties mean business. Hand-crafted waterproof rubber and sealed seams mean dry feet, and a faux-shearling lining insert means happy feet — which means you really can have it all in one of the season’s trendiest styles! A simple, classic style that does the job without the usual heavy-duty frills of other winter styles, these chic booties will take you from winter to spring and back into the rotation again come fall. It’s all about versatility when making seasonal purchases.

Ignite Rubber Waterproof Boot, Cougar, $160.

These Sperry classics may look casual enough to rock in any season, but these funky boots featuring mixed materials and colours pack enough of a punch to keep you toasty and dry through those chilly winter days.

Saltwater Duck Boot, Sperry, $160.

These lightweight cuties pack unparalleled traction on wet ice thanks to their special grip. Cute and functional, what more can you ask for? No need to brace yourselves for those super icy days. These are sure to become your mid-winter heroes.

Thermo Aurora 2 Shell Waterproof boots, Merrell, $225.