Men's Sale

Whether you like the classic Timberland boot aesthetic or prefer a contemporary twist on comfortable sneakers, you'll love our men's sale. From casual boots and waterproof men's hiking boots to men's sneakers and sneaker boots, our men's footwear sale has everything you need to look and feel good no matter what. 

Are you an outdoor enthusiast? Our Men's Mt. Maddsen Waterproof Mid Hiking Boot features anti-fatigue comfort technology for all-day comfort. TimberDry™ linings keep the feet snug no matter the weather. For a more stylish option, try the Men’s Arbor Road Waterproof Chukka in Wheat Full-Grain. 

Whether you're shopping for someone important or just looking for a new all-time favourite, the classic Timberland men's 6 inch boots can never go wrong. With our men's boots sale, you can get more footwear for your money. Keep an eye out for limited-time discounts on awesome styles, and make that special occasion a little extra special this year.

If you're not in the market for shoes, no problem. Our men's apparel sale has plenty of cool clothing and awesome accessories to explore.

Looking for some casual clothing for day-to-day wear? Try our Men's Timberland PRO® Core Lights Graphic T-Shirt in a colour that goes with everything. For cooler weather, the Men's Timberland PRO® Dryshift Waterproof Lightweight Jacket 2.0 features RainRepel™ technology to keep you protected from the elements. Keep an eye out for men's t-shirts, men's shorts and pants, men's jackets, and more in our men's clothing sale. 

Browse our collections for cozy men's sweatshirts and hoodies for the ultimate winter warmers. Our Men's Timberland Tree Logo Crewneck Sweatshirt comes in four colours. Try Wheat Boot/Black, Dark Olive, Dark Sapphire or Black/Wheat Boot for a pullover that combines comfort and style. For extra comfort and convenience, the Timberland Tree Logo Hoodie is a cotton-blend material with an adjustable hood and large front pocket for any essentials. And it goes great with our comfy sweatpants.

Whether you're stocking up on staples or doing an entire wardrobe refresh, our men's sale can help you look and feel good without blowing your budget. With colour options including plaid, blue, grey, brown, taupe, and more our shirts and pants are sure to meet your style needs. If you prefer something in a slim fit, we have plenty of options for you, too. 

Gearing up for a new job? Need to stock up on some reliable, comfortable, and super-durable workwear? Browse our men's sale now to find amazing discounts on men's work boots, work outerwear, and work shoes. 

Made from high-quality materials and designed to keep you safe and comfortable, you can rely on our men's workwear daily. From steel-toe boots and composite-toe sneakers to waterproof jackets and insulated coats, we've got everything you need to get the job done in comfort and style. 

Explore the Timberland men's on-sale styles today to find fantastic discounts on your favourite shoes, clothing, and more. Shop men's new arrivals and men's best sellers for more style inspiration and to see what's trending. Buying for a loved one? Shop women’s clothing for options she’ll love. 

Buy your new shoes and clothing online now for quick checkout and easy delivery to your home. Or use our store locator to buy in-store at a retailer in Canada near you.