Winter Boots & Shoes

From wet and windy days to super chilly nights, winter in Canada can be tough. With our men’s winter boots, you can keep your feet and toes cozy and comfortable no matter what. 

For a classic look, check out the Men's Timberland® Premium 6-Inch Waterproof Boot. Inspired by our iconic yellow boots, these men’s winter boots never go out of style. With anti-fatigue comfort footbeds, 400 grams of PrimaLoft® insulation, and durable rubber lug outsoles for superior traction, you can wear them day in and day out in true comfort. These boots also come in a variety of different colours. Go with wheat nubuck for the iconic and original Timberland style or choose all-black for a versatile and elegant look. If you enjoy experimenting, this classic boot also comes in red and green colours. 

Looking for a winter boot that can handle various terrains and conditions? Check out our field boots for men and gore-tex boots. Waterproof and insulated, they’re designed to keep you dry, warm, and comfortable no matter what. If you need something for challenging hikes and outdoor adventures, check out our wide range of men's hiking boots and shoes. From sneakers to ankle boots to high-cut boots and snow boots, there are plenty of options to choose from.

Once your feet and toes are nice and cozy in your new men’s winter boots, it’s time to think about the rest of your body. Whether you’re looking for comfy men's bottoms or cool and casual men's sweatshirts and hoodies for socializing with friends, our men’s clothing collection has got you covered. For warm and stylish waterproof and water-resistant protection wherever you go, make sure you check out our men's jackets and vests too.

Complete your winter outfit with our range of awesome accessories. From men's hats and socks for men to men's backpacks and men's gear, we’ve got everything you need to wrap up warm this winter. And, for some limited-time offers and discounted prices, make sure you check out our men's accessories sale too.

Whether you’re looking for day-to-day boots you can dress up or down for all sorts of occasions or want a purpose-built boot for work or outdoor adventures, explore our range of winter boots and men’s footwear online now to find the perfect fit for your feet. For even more style inspiration at great regular prices, check out our men's new arrivals and men's best sellers. 

Buy your men’s winter boots online today for quick checkout and easy delivery. If you’d prefer to try our men’s winter boots in-store first, you can use our store locator to find your nearest or most convenient Timberland retailer.