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Men's Timberland® Premium 6-Inch Waterproof Winter Boot
Men's Treeline Waterproof Tall Insulated Boots
Men's Timberland® Premium 6-Inch Waterproof Winter Boot
CAD 190.00 CAD 169.99
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LIMITED TIME- EXTRA 40% OFF
Men's Tree Vault 6-Inch Waterproof Boots
Men's Chillberg Mid Sport Waterproof Boots
Men's Ashwood Park Warm-Lined Chukka Boots
CAD 230.00 CAD 199.99
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LIMITED TIME- EXTRA 40% OFF
Men's Paint Splash 6-Inch Waterproof Boots
CAD 160.00 CAD 139.99
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LIMITED TIME- EXTRA 40% OFF
Men's Treeline Waterproof Insulated Boots

Guys across the globe have been wearing and loving our Timberland men's boots for more than 40 years. We've never stopped designing and innovating - and we never plan to. Our iconic Original Yellow Boot™ is at the heart of it all, but is joined by a range of high-quality leather boots, sneaker boots, chukkas, chelseas, and more. Every pair is crafted with style, comfort, durability, and the environment in mind.

Our men's boots are built for every occasion. Our waterproof boots are essential for rainy days and early spring as the snow melts, keeping your socks dry all day. Our hiking boots are flexible and comfortable, and let you move and climb the toughest trails. And our work boots are versatile and tough, ideal for any job site you throw at them.

Tough boots don't have to be uncomfortable. Try Timberland's always-comfortable boots with their suede interiors, cushioned soles, and structured insoles, and never go back to putting up with uncomfortable boots again. From our men's work boots to our relaxed weekend pairs, our boots provide support and grip across almost any surface.

When your work boots don't fit the dress code, our dress boots promise just as much comfort and durability - but with significantly more style. Try a casual ankle boot or chukkas for weekend wear, or slip on your safety-toes for heavy duty wear.

Questions about our men's boots? Visit our Help Center for answers to FAQs or to get in touch.