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Vans x Timberland® Premium 6-Inch Boots
Men's Jimmy Choo x Timberland® 6-Inch Puffer Boots
Men's Timberland® Premium 6-Inch Waterproof Winter Boot
CAD 130.00 CAD 109.99
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LIMITED TIME- EXTRA 40% OFF
Men's Seneca Bay Chukka Boots
Men's Ashwood Park Leather Slippers
Men's Trailquest Wateproof Hiking Boots

Browse our collection of men's footwear online. Rugged enough to deal with Canada's harshest winters and stylish enough to wear from the hiking trail to the restaurant, our men's boots tick all the boxes. Our sneakers, casual shoes, sandals, hiking shoes, and other styles all add something new to your wardrobe, ensuring you have a high-performance shoe no matter the occasion.

From PrimaLoft® ECO insulation for warmth and dryness to Gold and Silver tannery sources for better leather materials, every stitch in Timberland men's shoes is planned and prepared with superior craftsmanship and care. Our best sellers are an ode to our decades of experience in quality and style, such as our men's Timberland PRO™ work boots, which are a testament to our durable, comfortable footwear that last the distance.

Footwear that isn't as comfortable and supportive by the end of the day as it is at the start of the day has no business being on your feet. From the soles to the supports, each pair of Timberland men's shoes is designed with all-day comfort in mind. Our anti-fatigue technology and Ortholite® insoles work tirelessly to protect your feet from discomfort and sore points, while slip-resistant rubber soles help to keep you steady through wet and icy cold months.

Timberland men's shoes and boots are versatile. They can go anywhere, whether that's into bad weather in our waterproof boots, casual after-work drinks in a pair of chic chukkas or Chelsea boots, or out to the trails with our sneakers and sneaker boots for men. Dress them up with a collared shirt or down with a casual tee and you'll be prepared for any occasion.

Explore our new arrivals to see what's new right now.