Shirts

Whether you're looking for something comfortable and casual or smart and stylish, our collection of shirts for men has it all. Made with high-quality materials and designed to feel every bit as good as they look, our men's shirts are wardrobe staples you can wear season after season.

For days when you want to strike the right balance between dressy and casual, a Timberland men's shirt is a great place to start. From men’s sweatshirts and button-up shirts to flannel shirts and crisp overshirts, there are plenty of options for men.

If you're looking for a simple yet timeless option to elevate a casual outfit, check out the Men's Windham Brushed Twill Overshirt. Relaxed yet polished, it's the perfect combination of smart and casual. It also has a chest pocket with a pen holder, making it a practical option for a laid-back work outfit. Layer it over a men’s t-shirt for a subtle and effortlessly elegant look.

Do you prefer a more casual and rugged style? Take a look at the Men's Timberland PRO® Woodfort Lightweight Flannel Flex Shirt. It's durable and stretchy, made with Timberland PRO® FLEX technology. This men's shirt gives you a full range of motion for whatever your day has in store. Whether you want to wear it at work, to do some gardening, or for a casual social occasion, you'll be comfortable in this shirt for the duration. Pair it with our men’s PRO® work boots.

For a heavyweight men's shirt for cooler climates, check out the Men's Windham Heavy Weight Flannel Shirt. It's made with 300g of 100% cotton and designed to keep you warm, comfy, and cozy, whatever the weather.

Our men's shirts are durable, stylish, and versatile. Whether you prefer to wear regular-fit jeans or relaxed-fit cargo pants, you'll find shirts for men to match here. 

For a timeless outfit that you can wear season after season, pair your men's shirt with some jeans and a pair of classic Timberland men's boots. For extra warmth during winter, look for insulated boots and add a cozy beanie from our collection of hats, scarves, and gloves. 

Explore our collection of shirts for men to find your new go-to outfit. For more style inspiration, check out our new arrivals. For limited-time offers and discounts on shoes, clothing, and accessories, remember to browse our sale.

Buy your new men's shirts online today for quick and easy delivery. If you would prefer to try them in-store first, you can use our store locator to find a Timberland retailer near you.