Timberland's winter boot sale is knocking an extra 30% off sale styles — here's 11 deals I'd shop now

Timberland boots
(Image credit: Timberland)

Cold, rainy and snowy weather calls for a trusty pair of boots! And if you're in the market for a brand new pair, Timberland is offering some winter specials that you don't want to pass up.

Right now, Timberland is knocking an extra 30% off winter boots when you add the items to your cart. This discount is also applicable to footwear that is already on sale — meaning you're in for a great deal.

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Best Timberland Boot Deals

Timberland Westmore Moc-Toe Chukka Boot (Men's)
Timberland Westmore Moc-Toe Chukka Boot (Men's): was $100 now $62 at Timberland
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From the outdoors to the office, you'll love sporting these boots all season. Both functional and stylish, the boots are made with 100% organically grown cotton laces, a comfy EVA footbed, and a rubber outsole. Plus, they can help you tackle any trail with their support, flexibility and better stability on uneven surface.

Timberland Allington Mid Chelsea Boot (Women's)
Timberland Allington Mid Chelsea Boot (Women's): was $130 now $62 at Timberland
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These high-quality boots were made for dressing up in colder weather months. Made from premium Timberland leather and a fabric lining, these boots will match all your outfits whether you're heading to work or going out to dinner. They're also super comfortable thanks to their memory foam footbed.

Timberland Greyfield Chelsea Boot (Women's)
Timberland Greyfield Chelsea Boot (Women's): was $120 now $69 at Timberland
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A work boot with a contemporary design, these surprisingly lightweight boots are packed with benefits like leather uppers and a fabric lining containing at least 50% recycled plastic. Additionally, the boots are stylish, dependable and durable.

Timberland Roxie Lane Mid Lace-Up Boot (Women's)
Timberland Roxie Lane Mid Lace-Up Boot (Women's): was $130 now $69 at Timberland
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These versatile shoes are up for any adventure. Both functional and stylish, they're perfect for the trails and feature a memory foam footbed that will have you moving all day comfortably. This style is selling out fast, but there are two more colors that may still be available in your size.

Timberland Motion Access Waterproof Hiking Boot (Women's)
Timberland Motion Access Waterproof Hiking Boot (Women's): was $140 now $69 at Timberland
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Ready to get out on the mountain? This pair of hiking boots will be your trusty sidekick regardless of the weather. They're breathable, waterproof and feature fabric lining made from at least 50% recycled plastic. According to Timberland, this style tends to run small, so they recommend you buy ½ size larger than your normal size.

Timberland Nellie Chukka Boots (Women’s)
Timberland Nellie Chukka Boots (Women’s): was $140 now $69 at Timberland
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I've had my eye on a pair of Timberland boots for a while now, but it's always worth waiting for a sale to pick them up. At 30% off, these Nellie Chukka boots are made from premium Timberland leather, a rugged sole, OrthLite footbed and padded collar for added comfort. Easy to wear day in/day out and now at a great price.

Timberland Chillberg Waterproof Hiking Boots (Men’s)
Timberland Chillberg Waterproof Hiking Boots (Men’s): was $135 now $94 at Timberland
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If hiking's on the agenda, these waterproof, insulated hiking boots are perfect. In Timberland's classic colors and brand logo on the side, it's an iconic piece for the wardrobe that's also incredibly practical. And while they'd usually set you back $135, they're now under $100!

Timberland White Ledge Waterproof Mid Hiker Boot (Men's)
Timberland White Ledge Waterproof Mid Hiker Boot (Men's): was $120 now $109 at Timberland
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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 Mt. Maddsen Lace-Up Hiking Boot (Men's)
Timberland Mt. Maddsen Lace-Up Hiking Boot (Men's): was $120 now $109 at Timberland
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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. There are five different colors currently on sale.

Timberland Redwood Falls Waterproof Boots (Men’s)
Timberland Redwood Falls Waterproof Boots (Men’s): was $160 now $112 at Timberland
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This versatile boot is made with premium waterproof leather and is well-suited for those rainy days. Plus, a Gripstick rubber outsole will keep you firm on the ground in wet and dry weather, meaning a sturdy and comfortable walk.

Timberland Premium 14" Waterproof Boots (Women’s)
Timberland Premium 14" Waterproof Boots (Women’s): was $200 now $140 at Timberland
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If you've been looking for a pair of long black boots, this might just fit the bill. And $60 off won't hurt either. Timberland's great at making waterproof boots that keep your feet dry, alongside an anti-fatigue footbed which is a pretty cool addition.

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. 

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