The Best Winter Boots That Will Keep You Dry and Warm

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.

Step right into Aldo's Boot Shop and sniff out sweet options for this Canadian winter season. Of course, to keep you dry and warm, we love these Kozy knee high ones with the sporty-casual vibe. Up close or from six feet away, you'll look cute and weather appropriate.

Aldo Kozy Boots, $120.

This cozy, stylish boot will have your feet thinking it's May in the dead of this cold, Canadian winter. Roots' Womens Tuff Cabin Boot is waterproof — and comes with two sets of laces so you can switch up your pedestrian vibe. Very Instagram worthy and will add some personality to any of your best staples.

Womens Tuff Cabin Boot, $160.

This cute Timberland boot makes sporting the athleisure style possible through the cold winter months. This responsibly crafted piece of footwear contains recycled materials and is designed with a lining to help keep your human feet warm and toasty — while looking cool.

TImberland Londyn Warm Lined 6, $130.

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.

These classic shearling-lined boots are built for cold Canadian winters. The permanently rolled-down cuff gives them a trendier take. Keeping your comfort in check with the block heel, this bootie still manages to give you the boost you might like from a dressier shoe, without compromising on practicality.

UGG Esterly Genuine Shearling Boot, $232.

Not into traditional styles but still looking to stay warm this season? Sorel’s got you covered with this funky leather bootie. Crafted with waterproof leather and microfiber lining, you’re covered from anything the cold season might throw at you, not to mention looking stylish enough that you won’t have to change your footwear for a night out on the town.

Sorel Leather Bootie, $280.

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.

These cozy ankle booties are as comfy as they look. Crafted with faux-fur, you’ll be warm come rain or snow.

Zara Zip Ankle Boots, $50.

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.

For those in the know, winter boots have come a long way in terms of not only materials but the technology needed to keep savvy consumers feeling their footwear purchases are worth the costs. While smart-boot technology is not at the top of everyone’s list, there is definitely a market for those outdoorsy types who know what they want – and need – out of a great winter boot. These beauties protect you from frigid temps and boast 200g insulation as well as a thermal-reflective lining.

Columbia Women’s Loveland Shortie Boots, $90 (currently on sale for $75).

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!).