Members bag an extra 10% off most of these already-discounted items. (not a member? it's free to join.) Plus, Timberland Community Rewards members get free shipping on orders of $75.
This deal was good enough to make our roundup of the top five best deals of the day. Follow that link to see our latest selection. Shop Now at Timberland
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Published 5/28/2025
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Popularity: 5/5
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Staff PickDeals so good we bought one ourselves
That's $8 off and within $1 of the lowest price it's been. Buy Now at Amazon
- 100% genuine leather
- Includes attached flip ID pocket
- 5 card slots and 2 ID windows
- Slim profile design
- Offers organized storage
Shop over 25 men's boots at Timberland. We've pictured the Timberland Men's Gritstone 6" Steel Toe Work Boots for $75 ($50 off). Plus, Timberland Community Rewards members get free shipping on orders of $75. Shop Now at Timberland
While sizes are limited, this is the best deal we've seen for these shoes and a great deal for Timberland men's shoes in general. Buy Now at Nordstrom Rack
The headline advertises up to 40% off but we found deeper discounts in the Timberland brand outlet at eBay. The pictured Timberland Men's Boondock HD 6" Composite Toe Work Boots are $97.99, 63% off. Plus you'll get free shipping on these orders. Shop Now at eBay
Shop over nearly 20 discounted On styled during Nordstrom's Half-Yearly Sale. Prices are as marked. Everything ships for free. Shop Now at Nordstrom
Shop over 60 discounted pairs. We've pictured the Skechers Men's Flex Advantage 5.0 Arlus Casual Sneakers for $40 (low by $16). Star Rewards members receive free shipping on orders over $25 (it's free to join). Non-members can pay $10.95 or get free shipping on orders over $49. Pickup is available on most orders, too. Buy Now at Macy's
You will find deep discounts on over 4,000 items from adidas, Patagonia, Nike, and more. Prices start as low as $2. Orders of $65 or more get free shipping; otherwise, choose pickup (where available) to avoid the $8.99 shipping charge. Shop Now at Going, Going, Gone
You can save on all sorts of men's bottoms bundles in this sale today at Woot, including shorts, pants, and belts. Pictured is the Blu Rock Men's Straight Leg Jeans 3-Pack, which is just $35 (you'd pay $59 for a 2-pack at Macy's). Buy Now at Woot! An Amazon Company
Timberland has 9 men's sneakers and sneaker boots discounted up to 60% off. We've pictured the Timberland Men's Men's Motion Scramble Low Lace-Up Waterproof Hikers for $100 ($40 off). Plus, Timberland Community Rewards members get free shipping on orders of $75. Shop Now at Timberland
Prices start at $40 and are as marked. We've pictured the Timberland Men's Radius Knit Comp-Toe Slip-On Work Sneakers for $60 (low by $40). Plus, Timberland Community Rewards members get free shipping on orders of $75. (It's free to join.) Shop Now at Timberland
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