Hiking Boots & Shoes

Timberland men’s hiking boots combine quality, comfort, breathability, and style. With cutting-edge technology like TimberCush™ comfort systems and GreenStride™ midsoles, they’re built for superior performance and supreme comfort throughout all conditions in Canada.   

For a comfortable, rugged, and casual look that works on and off the trail, check out the Men's Flume Waterproof Mid Hiker Boot. With a Premium Timberland® leather upper, these waterproof hiking boots provide ultimate ankle support through any terrain. The EVA footbed and compression-moulded EVA midsole combined with seam-sealed construction ensure your feet remain comfortable and secure no matter the elevation. Meanwhile, the classic dark brown colour gives these boots a rugged styling.

If you’re looking for the comfort, traction, durability, and support of a boot but with the lightweight feel of a sneaker, you’ll love our hiking shoes for men. 

For a comfortable, rugged, and casual look that works on and off the trail, check out the Men's Motion Access Low Lace-Up Sneaker. These hiking boots for men feature the TimberCush™ comfort system that supports your feet and offers cushioning all day long. These best-selling shoes also come with a TimberGrip™ lug outsole that provides extra traction. You won’t have to worry about slippery surfaces in these shoes. Best of all, these sneakers were designed with the environment in mind with Premium Timberland® Leather and ReBOTL™ fabric made from 50% recycled plastic. As you lace up for your next adventure, you can relax knowing that you’re doing your part to protect our planet.

Or try the Men’s GreenStride™ Motion 6 Hiking Shoe. With a GreenStride™ midsole using an EVA blend for the ultimate in comfort and a ReBOTL™ fabric lining for sustainability, these shoes were made for comfort and accessibility. Fifty-five percent of the outsole rubber comes from regenerative agriculture farms, so you and your feet will feel fantastic about these hiking sneakers. 

Once you’ve found your ideal pair of men’s hiking boots or shoes, it’s time to load up on accessories. For a cozy and comfortable feel no matter what, make sure you stock up on some Timberland socks. For weather protection from head to toe, add season-appropriate headwear. From trucker caps to beanies, we’ve got hats for every climate. Go for a warm beanie to protect you from the cold, or a baseball cap to shield you from the sun.

To keep all your snacks, gear, and extra layers within easy reach, don’t forget to invest in one of our backpacks and bags. The Calverton 26-Liter Backpack is a versatile and casual carrying essential for weekends with friends. The Performance Hiking Cross Body Pouch is as stylish as it is functional. It comes with multiple compartments allowing you to easily access any belongings on-the-go. No matter what your style preferences are or what occasion you’re attending, there’s a backpack or bag for everyone.

Find the perfect pair of shoes for your next big adventure with our men’s hiking collection. Discover more styles at low prices through our men’s footwear sale. Be sure to visit our new arrivals before you checkout. If you’re shopping for the family, browse our women’s and kid’s selections for top women’s hiking boots and kids’ boots. 

Buy your new men’s waterproof hiking shoes online today for quick and easy delivery. If you prefer to try our shoes and boots in-store, use our handy store locator to find your nearest Timberland retailer.