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 perfected for Canadian winters. These waterproof mukluks promise to be the warmest, most comfortable winter boots you’ll ever step into, and we can see why. The boots are breathable, and made of sheepskin 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 boot’s flexible and durable sole promotes circulation and offers barefoot-like comfort. They are not only beautiful to look at, featuring Indigenous artistry, but they also help support local Indigenous communities too. 

Manitobah Mukluks Waterproof Snowy Owl, $250

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 Sherpa 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. They are fully certified vegan, handmade and come with a 2 year warranty. 

Hunter’s Women's Tall Insulated Rain Boots, $195

An affordable option for those looking for a trendy (read: chunky) take on the classic chelsea boot, PrettyLittleThing’s off-duty Large Cleat Extra Chunky Sole boot will keep you above the winter slush and looking cute in the process. It’s faux leather and features zip fastening.    

PrettyLittleThing Black PU Large Cleat Extra Chunky Sole Chelsea Boot, $74

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

Aldo Miriacan Chelsea Boot with Lug Sole, $150

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 ba&sc scru. Santiago-styled cowboy boots 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 are made in Portugal and are decorated with ba&sh’s iconic signature scrolled topstitching. The vintage feel comes from the boot’s leather, which like real cowboy leather, is initially thick and stiff, but gradually shapes to each individual when worn. Other hot tip, ba&sh now has them for 50 per cent off. 

ba&sh scru. Cowboy Boot, $353

This fashion-forward take on the classic Sorel Joan of Arctic boot comes in three colours and offers a cool, street-ready weather boot that’s water-resistant and warm. Featuring microfleecing lining and 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 Joan Of Arctic Next Lite Boots, $240

Another cold-weather favourite, Roots made the Jasper Winter Boot to be waterproof and warm. It has a premium leather shaft, a winter rubber shell and is insulated with a fleece liner to keep your feet warm and dry. The brand’s trademark Ortholite Eco-Hybrid insoles will also keep you comfortable as you walk.

Roots Womens Jasper Winter Boot, $198

Love it or hate it, the UGG is 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, $195

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

Free People Stevie Boot, $413

This icon 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.

Farfetch Moon Boot Icon Snow Boots, $196

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.

Dr. Marten Serena, $220.

Coming in at only two pounds, 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, $200.

Heavy-duty and heavily chic, these tall lace-up winter boots feature a lugged sole and faux fur trim. 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. Snowball fight, anyone?

Aldo Powder Boots, $135.

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 Jacobsen Rubber Boot, $276.

This cute leather bootie from Timberland features the brand's exclusive MirrorFit system that offers personalized comfort. Sustainability was taken into consideration when crafting these boots as they are made with 50 per cent recycled plastic and leather treated through an energy efficient process. Look and feel good this winter with this style.

Timberland Graceyn Waterproof Biker Boots, US $150.

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 the classic short boots from Ugg. Shearling-lined, cozy and crafted with adventure in mind, these lightweight boots won’t weigh down your luggage and can be squished into even the smallest of spaces. Now all you need is the destination!

Ugg Classic Mini II Boot, $193.

What could be cooler, or more practical for those 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 fun colour options and quilted-effect of these from the authority in rain boots, Hunter!

Hunter Refined Slim Fit Adjustable Quilted Tall Rain Boots, $220.

These brown leather boots may look more fashion than function, but don’t be fooled by their good looks, these beauties mean business. Waterproof leather and sealed seams mean dry feet, and a memory foam 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 – for more staples worth the money, see our list of the best fall investment pieces this season!

Kodiak Alma Chelsea Boots, $180.

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.

Sperry Saltwater Duck Boots, $150.

These premium-quality suede platform 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. Fully-lined with a side zip, once you slip into these comfy boots, you may never want to take them off.

HM Suede Platform Boots, $99 (currently on sale for $50!).