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Timberland boots are up to 50% off — here’s 9 styles worth shopping for fall
Olivia Halevy
17 September 2025
Shop must-have boots for fall
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Fall is just a few days away — which means boots season (aka the most wonderful time of the year) is rapidly approaching. If you’re in the market for a brand new pair, there’s no better place to shop than Timberland, especially now that they’re currently knocking up to 50% off fall styles.
For starters, you can grab the Timberland White Ledge Mid Waterproof Hiking Boot on sale for $99. These are perfect to keep up with all your outdoor adventures, this fall and beyond. If you’re in the market for something a little more stylish to wear on an everyday basis, I recommend the Timberland Westmore Moc-Toe Chukka Boot for just $59.
When it comes to the ladies, you can’t got wrong with the Timberland Roxie Lane Mid Lace-Up Boot for just $99. If you’re looking for a dressier pair of booties that feature a heel, I suggest the Timberland Allington Mid Chelsea Boot for $79.
There’s plenty more deals where those came from! Keep scrolling to check out my favorite boot deals from the Timberland sale.
Quick Links
shop all Timberland deals
Timberland Westmore Moc-Toe Chukka Boot (Men’s): was $100 now $59
Timberland Brimfield Mid Chelsea Boot (Women’s): was $150 now $69
Timberland Allington Mid Chelsea Boot (Women’s): was $130 now $79
Timberland Linden Woods 6-Inch Waterproof Boot (Women’s): was $130 now $99
Timberland White Ledge Waterproof Mid Hiker Boot (Men’s): was $120 now $99
Timberland Roxie Lane Mid Lace-Up Boot (Women’s): was $130 now $99
Timberland Pro Magnitude 6″ Waterproof Comp-Toe Work Boot (Men’s): was $200 now $139
Best Timberland Boot Deals
Timberland Westmore Moc-Toe Chukka Boot (Men’s): was $100 now $59 at Timberland
From the outdoors to the office, you’ll love sporting these boots all fall. 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 Brimfield Mid Chelsea Boot (Women’s): was $150 now $69 at Timberland
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 Allington Mid Chelsea Boot (Women’s): was $130 now $79 at Timberland
These high-quality boots were made for fall (and beyond). 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 Linden Woods 6-Inch Waterproof Boot (Women’s): was $130 now $99 at Timberland
These ankle boots offer versatility, function — and protection for the elements. Not only are they stylish, but they also have rubber lug outsoles for excellent traction and grip on slippery surfaces.
Timberland Roxie Lane Mid Lace-Up Boot (Women’s): was $130 now $99 at Timberland
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.
Timberland White Ledge Waterproof Mid Hiker Boot (Men’s): was $120 now $99 at Timberland
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): was $120 now $109 at 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. There are five different colors currently on sale.
Timberland Premium 6-Inch Waterproof Boot (Women’s): was $170 now $119 at 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!
Timberland Pro Magnitude 6″ Waterproof Comp-Toe Work Boot (Men’s): was $200 now $139 at Timberland
If you need a heavy duty work boot, this is the optimal choice. They feature industrial-grade protection from every angle while tackling slippery and wet job sites thanks to their waterproof leather uppers and internal waterproof membrane. You can feel confident that your feet will stay dry and protected!
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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.
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