Huge Timberland sale is live from $49 — 15 winter boot deals I’d shop now

Timberland Deals
(Image credit: Amazon)

'Tis the season for winter boots — especially if you live in a particularly cold, wet or snowy climate. Not sure where to shop? Timberland has you covered whether you're shoveling snow in your driveway or hitting the hiking trails this winter.

Timberland is a footwear brand best known for its iconic yellow work boots — but they also happen to make high-quality, weatherproof winter boots, too. Even better? Timberland is currently hosting a huge sale with up to 40% off select styles for both men and women.

With sturdy, warm and comfortable boot options starting at just $49, I recommend shopping the deals ASAP. Below, I've rounded up my favorite styles from the Timberland sale.

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Best Timberland Deals

Timberland Ellendale Mid Lace-Up Boot (Women's)
Timberland Ellendale Mid Lace-Up Boot (Women's): was $100 now $49 at timberland.com

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."

Timberland GreenStride Atwells Ave Waterproof Chukka Boot (Men's)
Timberland GreenStride Atwells Ave Waterproof Chukka Boot (Men's): was $145 now $49 at timberland.com

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.

Timberland Skyla Bay 2.0 Mid Warm Lined Sneaker (Women's)
Timberland Skyla Bay 2.0 Mid Warm Lined Sneaker (Women's): was $90 now $49 at timberland.com

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.

Timberland Maple Grove Sneaker (Men's)
Timberland Maple Grove Sneaker (Men's): was $110 now $69 at timberland.com

These Timberland sneakers 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.

Timberland Mt. Maddsen Mid Lace-Up Hiking Boot (Men's)
Timberland Mt. Maddsen Mid Lace-Up Hiking Boot (Men's): was $110 now $79 at timberland.com

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.

Timberland Britton Road 7-Eye Moc Toe Boot
Timberland Britton Road 7-Eye Moc Toe Boot: was $170 now $84 at timberland.com

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.

Timberland Gritstone 6" Steel Toe Work Boot (Men's)
Timberland Gritstone 6" Steel Toe Work Boot (Men's): was $125 now $84 at timberland.com

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.

Timberland Chocorua Tall Lace-Up Waterproof Snow Boot (Women's)
Timberland Chocorua Tall Lace-Up Waterproof Snow Boot (Women's): was $170 now $84 at timberland.com

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!

Timberland Brimfield Mid Chelsea Boot (Women's)
Timberland Brimfield Mid Chelsea Boot (Women's): was $150 now $89 at timberland.com

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.

Timberland Converge Mid Lace-Up Waterproof Boot (Men's)
Timberland Converge Mid Lace-Up Waterproof Boot (Men's): was $160 now $94 at timberland.com

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."

Timberland Redwood Falls Waterproof Boot (Men's)
Timberland Redwood Falls Waterproof Boot (Men's): was $145 now $99 at timberland.com

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."

Timberland Authentics Waterproof Roll-Top Boot (Women's)
Timberland Authentics Waterproof Roll-Top Boot (Women's): was $170 now $99 at timberland.com

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.

Timberland Chillberg Waterproof Insulated Boot (Men's)
Timberland Chillberg Waterproof Insulated Boot (Men's): was $150 now $99 at timberland.com

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.

Timberland White Ledge Waterproof Mid Hiker Boot (Men's)
Timberland White Ledge Waterproof Mid Hiker Boot (Men's): was $120 now $99 at timberland.com

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.

Timberland Premium 6-Inch Waterproof Boot
Timberland Premium 6-Inch Waterproof Boot: was $170 now $109 at timberland.com

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!

Olivia Halevy

Olivia is a Deals Writer at Tom’s Guide. She loves all things lifestyle, shopping, and sourcing the best deals from some of the top brands, retailers, and websites around. From fashion and beauty to smart home and tech, she has an eye for finding practical, stylish, and reasonably-priced items that help make life simpler (and a little more aesthetically-pleasing). Olivia has over five years of experience writing lifestyle, commerce, and branded content for Patch.com. In her free time, she enjoys trying out new exercise classes, binge-watching the latest viral TV shows, cooking, spending time with family, and taking long walks with her dog, Gus.