Huge Timberland sale is live from $49 — 7 winter boot deals I’d shop now

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Upgrade your winter boot game for less

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."

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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.

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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!

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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."

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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.

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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.

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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!

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Olivia Halevy
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.