Waterproof Boots & Shoes

Whether you need sturdy boots for active adventures in Canada or smart-casual boots for year-round wear, you'll find something for every style and occasion in the Timberland men's waterproof shoes collection. From ankle boots and shoes to work boots, we’ve got your feet covered.

Need something smart-casual you can wear to the office and after work socializing? Or are you looking for a stylish fashion shoe that can endure any weather? Either way, look no further than our men's waterproof shoes.

If you're looking for a sturdy yet elegant option that works for meetings or winter dates, take a look at our Men's Redwood Falls Chelsea Boot. These waterproof shoes are durable and stylish with premium Timberland® leather uppers, steel shanks for arch support, Gripstick™ rubber outsoles, and our patented L7 lug design. Choose from three versatile colours to find a shade that works for your wardrobe. Dress them down with skinny jeans for an effortlessly smart-casual look.

For a timeless aesthetic that transitions seamlessly from work to casual settings, try our Iconic Waterproof Boot.  Choose your color and enjoy the comfort of our anti-fatigue technology and excellent arch support.

The Men’s Lincoln Peak Lite Waterproof Slip-On Hiking Shoe is an excellent option for those who prefer to hike in a shoe. Built-in a convenient slip-on style for added accessibility with a rubber lug outsole and a waterproof leather upper, this waterproof hiker provides robust protection with a lightweight feel. It’s available in black suede in sizes from 7 through 15. 

Our collection of waterproof boots and shoes come in a variety of sizes, colours, and designs. From chukka boots to waterproof hiking shoes and work boots, there's no shortage of styles and options to choose from. Whether you're a size 7 or 15, browse our selection online now and find the right shape and fit for your feet.

Check out our men's new arrivals and best sellers for even more footwear styles and designs. For durable and comfortable workwear, check out our Timberland PRO® range. 

Don't miss out on sale prices and exclusive offers on our regular price on a wide range of footwear and clothing in our sale before you checkout.

Buy your new waterproof men's shoes online today. Or, if you prefer to try in-store before you buy, use our store locator to find your nearest Timberland retailer selling men’s and women’s winter boots, hiking shoes, rain boots, work boots, snow boots and slip-ons.