Whether it's for cold-weather commutes or weekend walks in Canada, every man needs a good winter jacket he can rely on in unpredictable conditions. With our collection of men's vests and jackets, you can layer up in style no matter what. From fleece zip-ups to insulated jackets to wind-resistant coats, we've got a range of men’s outerwear to choose from, in sizes from XXS to XXL and above. 

For a simple and super warm option that you can wear with almost any outfit, check out our Men's Axis Peak Durable Water-Repellent Jacket. It keeps you warm and dry from the inside out and the outside in, with 100% recycled nylon fabric for sustainability and a breathable and water-repellent outer layer. Wear over a simple men's t-shirt for a casual look. For an extra touch of warmth, add one of our men's sweatshirts and hoodies as a cozy layer piece.

If you like hiking or working out in nature, you'll love our Men's Caps Ridge Mobi Flex Tech Waterproof Jacket. This men's jacket is made with 100% recycled polyester, which is waterproof and windproof.  The underarm vents, ergonomic sleeves, neoprene chin guard, and adjustable hood and cuffs also provide extra comfort in a way that works for you. Thanks to our cutting-edge DryVent™ technology, it's super breathable, too. If you love working up a sweat in the rain, you can enjoy customized comfort and uninterrupted performance in style.

Looking for something laid-back you can style with a variety of outfits? Take a look at our Men's Trucker Insulated Denim Jacket. Iconic and timeless, it's the perfect addition to any closet.

Are you a fan of the canvas vibe? Check out the Men's Strafford Washed Canvas Jacket. Made from double-woven cotton canvas with 25% recycled post-industrial cotton, you’ll wear it confidently knowing you’re helping the environment. This jacket is a versatile piece that’ll never go out of style. Pair it with Timberland’s selection of boots for men to complete the relaxed yet rugged look.

If you want the warmth and coziness of a jacket without the full coverage, you need a vest for men. From puffer to fleece vests, you'll find a range of versatile options in our men's vests collection. The best part about owning a men’s vest is that there are endless ways to style it. Layer a men’s vest over a long-sleeved top and add a pair of comfy men's bottoms to complete the look.

Try a casual pair like the Men's Linear Logo Sweatpant with a puffer vest on top. You’ll stay comfortable and warm throughout the day. For a casual look that works on the job or on the go, opt for our Men's Timberland PRO® Tempe Jogger Pants. These pants are made for comfort, accessibility, and functionality.

Browse our selection of men's jackets and men’s vests online today to find your new go-to outerwear. Take a look at our new arrivals for more style inspiration and to see what's trending. If you prefer the tried, tested, and timeless look, check out our best sellers. For more deals on Timberland remember to peek at our sale before heading to checkout.