Timberland boots are up to 40% off right now — here’s 15 winter deals I'd add to my cart

These trail-ready boots are the perfect pick if you're heading outdoors. The uppers are made of premium leather and durable polyester and they're also water-repellant, so they'll look good longer. Not only did they receive a 4.5 star rating online, but one happy customer mentions, "They are so comfortable right out of the box and I get so many compliments on them."
Price Check: $49 @ Timberland

Only a few sizes are left in stock, but this is an incredible saving on the Timberland GreenStride Chukka Boots. These are made of waterproof leather, so they're perfect for wet weather walks.

Want some sneakers that keep your feet warm? The Skyla Bay 2.0 does the job. They have a leather outer with have a faux fur collar and lining. Plus, the stretch panel at the side makes them easy to put on.

These Timberland Chukka boots have a premium leather upper and a soft fabric inner, so you can wear them without socks, if that's your thing. Plus, their brown and white color scheme means they stand out from the crowd.
Price Check: $79 @ Timberland

These Timberland hiking boots are perfect to keep your feet protected on the trails. They have tough traction outsoles and an EVA midsole for comfort. Only a few sizes are left in stock, so get these while you can.
Price Check: $79 @ Timberland

Score an epic 50% discount on these Britton Road 7-Eye Moc Toe Boots. Equipped with the TimberCush cushioning system, these feel like walking on a cloud according to Timberland. They're also breathable and have traction outsoles.

Durable, rugged and built to protect in many different environments (including electrical hazards), this steel safety-toe work boot is the ideal pick if you're looking for a comfortable boot to wear all day long. The boots features an abrasion-resistant rubber outsole using cement construction for flexibility and a breathable, moisture-wicking mesh lining.

Hoping to head out into the snow? Gear up for the winter weather in these lace-up waterproof snow boots that are stylish, comfortable and warm — a triple threat if you ask me!

Built to be comfortable, durable and of course, stylish, these Chelsea boots are perfect for every day wear. They feature all-day cushioning, support and a custom fit. Plus, their sturdy rubber lug outsoles are designed to provide all-weather traction.

Whether you're on or off the trail, you can feel confident with the waterproof boot that was designed for grip and crafted with sustainable materials. Another 4.5 star option, one reviewer wrote, "I wore them fishing and hiking and immediately felt like they were designed for my feet. Very comfortable and very true to size."

Let's face it: the winter can be harsh. That's why you need a boot that can help protect you from the elements. You’ll want this rugged, waterproof and insulated Timberland boot that's designed to be durable through hours of cold conditions, while helping your feet stay warm and dry.
Price Check: $99 @ Amazon

Boasting 4.5/5 stars with tons of positive reviews, these waterproof boots feature superior traction and a comfortable fabric lining. One happy customer wrote, "When I tried on these Redwood shoes, it was a game-changer for me. The shoes fit perfectly — neither too tight nor too loose, with no discomfort."

These Timberland boots are on sale for an awesome $70 discount. Their light brown nubuck coloring is super easy on the eyes, and they have a fuzzy faux-fur lining. Better yet, the tops can be worn rolled up or down to switch up these boots' look.

A no-brainer for your next outdoor adventure, this hiking boot is built with waterproof premium leather and features seam-sealed construction to protect against the elements. Plus, they have a rubber lug outsole for traction on the trails.
Price Check: $99 @ Timberland

These bold boots can stand up to the challenge of a rainy day thanks to their waterproof seam-sealed construction. The boot is available in a variety of colors, although this light beige hue is one of the only options on sale. They feature a 4.6 rating with nearly 2,000 positive reviews, so I would grab a pair today!