This site has limited support for your browser. We recommend switching to Edge, Chrome, Safari, or Firefox.

FREE SHIPPING on Canadian orders over $150* 📧 info@heelboy.com 📞 (416) 367-4335

Our Top Winter Boot Picks!

It's officially the first day of winter, and you know what that means. It's time for some new boots to help get you through the snow to wherever you need to be! If you haven't gotten your winter boots yet, keep reading for our recommendations of all the best ones. Whether you're looking for something trendy, cozy, or classic, we're confident you'll find the perfect pair to keep you warm and dry this winter season!

If you hadn't noticed, we're obsessed with Chelsea boots. They're the foundation of every well-equipped wardrobe thanks to their versatility and easy on and off. So, why not bring these benefits into your winter footwear wardrobe? These Chelsea boots are equipped with insulation, traction, and waterproofing for those days when you don't want to choose between style and warmth.

From top to bottom: Aquatherm Chloelo in Black, Cougar Ignite in Green, UGG Markstrum in Stout

These cozy boots are the definition of fashion meets function. Their plush and faux fur accents make them the perfect 'incognito' snow boots; you would never know they're waterproof just by looking at them! Pair them with leggings and your favourite oversized cardigan to embody the cozy look this winter.

From top to bottom: Sorel Explorer II Joan Cozy in Ancient Fossil/Sea Salt, Cougar Vanetta in Pewter, Sperry Torrent Winter Lace Up Boot in Ivory

If you're chronically cold, we recommend a tall winter boot to provide extra protection from the winter weather. Whether you're looking for something sleek and chic or more classically 'winter,' we have the perfect tall boots to help you carry over the knee-high trend into the colder months. 

From top to bottom: Aquatherm Poppy2 in Black, Sorel Joan of Arctic WP in Fawn/Omega Taupe, Valdini Kelly in Black

More into the classics? These boots are winter staples for a reason. Premium materials, impressive warmth, and waterproofing technology will keep you protected form the harsh winter elements for years to come!

From top to bottom: Sorel Tivoli IV WP in Black, UGG Adirondack III in Chestnut, Santana Canada Majestaluxe in Bordeaux/Bordeaux

'Après Ski' fashion is having a major moment this winter. Whether you're hitting the slopes or not, get in the snowy spirit with a pair of bright white boots! Complete the look with a pair of fluffy earmuffs and a hot drink in hand.

From top to bottom: UGG Adirondack Boot III in White Patent, Sperry Saltwater Alpine Leather in White, Religious Comfort Passion in White

From rugged work boots to snow-proof Sorels, find your new winter go-tos for everyday wear or extreme weather conditions. Deliver on all fronts—style, grip, warmth, and waterproofing—in a pair of our favourite men's winter boots.

From top to bottom: UGG Emmett Boot Mid in Chestnut, Sorel Caribou WP in Black/Dark Shadow, Sperry Cold Bay in Brown

Leave a comment

Please note, comments must be approved before they are published

Cart

No more products available for purchase

Your cart is currently empty.