Waterproof Boots & Shoes

Whether you’re hiking backcountry trails in Canada, working outside, or going for a casual dinner, our men’s waterproof shoes will get you there in style. From rugged boots to smart shoes and everything in between, our men’s waterproof shoe collection is designed to protect you from the elements and then some.

When it comes to men’s waterproof work boots, you’ve got to love a timeless classic. The iconic Men’s Timberland® Premium 6-Inch Lace-Up Waterproof Boot is not just waterproof but also loaded with PrimaLoft® insulation for comfort and warmth. With padded collars, a steel shank for arch support, and an anti-fatigue removable footbed for supreme cushioning, these waterproof leather boots are as cozy as they are practical. 

For a similar look in a broad range of colours, check out the Men’s Timberland® Premium 6-Inch Waterproof Boot. You can’t go wrong with our most versatile boots that have been around for decades. Our technologically advanced features ensure that you’ll stay warm and dry in any weather condition. Pair our iconic men’s waterproof boots with sweatpants, jeans, or any other men's bottoms for a casual look that lasts season after season.

If you’re looking for something durable and waterproof yet elegant enough for smart-casual occasions, check out our Men’s Redwood Falls Lace-Up Waterproof Shoe. With Premium Timberland® Leather on the outside, OrthoLite® footbeds on the inside, and Gripstick™ rubber outsoles underneath, they’re practical, comfortable, and graceful in equal measure. Pair them with slim-cut or tailored pants for a put-together look. Slip on jeans or chinos for laid-back sophistication. 

Need waterproof shoes for men who love to explore the great Canadian outdoors? We have a wide range of waterproof men's hiking boots to choose from. If you’re trekking on rugged terrain, keep an eye out for waterproof hiking boots with rubber lug outsoles for the ultimate traction. For ankle support, look for hikers with a higher cut. For light yet fully waterproof hiking shoes, check out our hiking sneakers.

Pair your men’s waterproof sneakers with a men’s jacket or vest for full protection from head to toe. Look for options that are both waterproof and breathable so that you stay dry from the inside out as well as the outside in. For even more comfort on the trail, don’t forget to pick up a few pairs of socks, too.

Browse our waterproof boots and shoes today to find the best fit for your feet. Whether you need something casual for day-to-day wear or want high-performance shoes for your next adventure, we’ve got you covered.

Buy your new men’s waterproof shoes online now for quick and easy delivery to your home. If you prefer to try our shoes in-store, you can use our handy store locator to find your nearest Timberland retailer. Shopping for the whole family? Be sure to browse our new arrivals and best sellers for the latest men’s, women’s, and kids’ styles before you checkout. And stop by our sale section for sale prices on some of our top items.