Shoes

If you’re looking for men’s boots, sneakers, and casual shoes you can dress up or down for almost any occasion in Canada, you’ve come to the right place. From chukkas to boat shoes to men's hiking boots to men's sneakers, our men’s footwear collection has everything you need to lace up in style, no matter the season.

Go from day to night in effortless style with our collection of high-quality boots for men. From Chelsea boots to Oxfords shoes, whether you’re looking for men’s work boots or men’s boots, Timberland has all sorts of men’s shoes for your personal style. 

Timberland is known for making stylish and comfy yet sturdy men’s footwear. We make more than just footwear for men. If you like the comfort and quality of our men's footwear but need a lighter shoe for smart-casual occasions, check out our Men's 3-Eye Lug Handsewn Boat Shoe. With leather lining for durability and rubber lug outsole for superior traction, these slip-on shoes are as practical and robust as they are timeless.

If you’re looking for a smart-casual dress shoe that pairs well with chinos, look no further than our waterproof lace-up shoes. From our Redwood Falls Lace-Up Waterproof Shoe to our Britton Road Lace-Up Waterproof Shoe, we have plenty of elegant styles to choose from. Whether you’re heading to a meeting or a first date, you can lace up with confidence.

Are you looking for the best shoes for a relaxed and ready-for-anything vibe? Swap your men’s footwear for some casual Timberland sneakers. If you love the ankle or high-top aesthetic, check out our Men's Maple Grove Mid Lace-Up Sneaker. These rubber sole shoes include 55% recycled rubber and come in a range of colours, from Medium Brown Full-Grain to Light Taupe Nubuck to Black. With all the toughness, traction, and breathability you’d expect from our men's boots with a chilled-out vibe, it’s the perfect casual shoe for day-to-day wear.

Prefer a sneaker with a low top? Try the Men's Motion Access Low Lace-Up Sneaker. With Premium Timberland® leather, an EVA midsole for cushioning, and a TimberDry™ waterproof membrane, they’re the ideal walking shoes to suit various outfits and occasions. Choose Black for a versatile and simple look, or opt for the Light Taupe Mesh design for a more casual look.

Explore our best men’s shoes, sneakers, and boots today to find your favourite new go-to shoes. For more style inspiration, check out our new arrivals and best sellers. On your way to the checkout, peek at our sale for great deals and limited-time offers on a range of men's footwear and men's clothing. 

Buy your men’s boots and more online now for quick and easy delivery. If you'd prefer to try our products in-store, use our store locator to find your nearest Timberland retailer.