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Items 241-279 of 279

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  1. Men’s Long Sleeve Plaid Woven Overshirt Men’s Long Sleeve Plaid Woven Overshirt
    Men’s Long Sleeve Plaid Woven Overshirt
    $95.99 $149.99
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  2. Men’s Long Sleeve Windham Heavy Flannel Shirt Men’s Long Sleeve Windham Heavy Flannel Shirt
    Men’s Long Sleeve Windham Heavy Flannel Shirt
    $69.99 $139.99
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  3. Men’s Windham Cotton Hemp Denim T-Shirt Men’s Windham Cotton Hemp Denim T-Shirt
    Men’s Windham Cotton Hemp Denim T-Shirt
    $99.99 $179.99
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  4. Long Sleeve Icon Boot Graphic Tee Long Sleeve Icon Boot Graphic Tee
    Long Sleeve Icon Boot Graphic Tee
    $19.99 $59.99
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  5. Carrier Tee Carrier Tee
    Carrier Tee
    $19.99 $59.99
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  6. Carrier Tee Carrier Tee
    Carrier Tee
    $29.99 $59.99
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  7. Stack Logo Tee Stack Logo Tee
    Stack Logo Tee
    $39.99 $59.99
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  8. Stack Logo Tee Stack Logo Tee
    Stack Logo Tee
    $39.99 $59.99
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  9. Men's Davis Square Oxford Basic Sneaker Men's Davis Square Oxford Basic Sneaker
    Men's Davis Square Oxford Basic Sneaker
    $59.99 $179.99
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  10. Millers River Pique Polo Shirt Millers River Pique Polo Shirt
    Millers River Pique Polo Shirt
    $39.99 $79.99
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  11. Men's Classic 6-Inch Waterproof Boot Men's Classic 6-Inch Waterproof Boot
    Men's Classic 6-Inch Waterproof Boot
    $99.99 $279.99
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  12. Men's Premium 6-Inch Waterproof Boot Men's Premium 6-Inch Waterproof Boot
    Men's Premium 6-Inch Waterproof Boot
    $129.99 $349.99
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  13. Men’s Ski School Timberland® Premium 6 Inch WP Boot Men’s Ski School Timberland® Premium 6 Inch WP Boot
    Men’s Ski School Timberland® Premium 6 Inch WP Boot
    $249.99 $369.99
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  14. Men's Premium Chukka Men's Premium Chukka
    Men's Premium Chukka
    $139.99 $329.99
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  15. Men's GreenStride™ Atwells Ave Waterproof Chukka Boot Men's GreenStride™ Atwells Ave Waterproof Chukka Boot
    Men's GreenStride™ Atwells Ave Waterproof Chukka Boot
    $129.99 $259.99
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  16. Dunstan River Tee Dunstan River Tee
    Dunstan River Tee
    $29.99 $59.99
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  17. Men's Atwell Ave Chelsea Boot Men's Atwell Ave Chelsea Boot
    Men's Atwell Ave Chelsea Boot
    $99.99 $259.99
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  18. Men's Classic Boat Shoe Men's Classic Boat Shoe
    Men's Classic Boat Shoe
    $119.99 $199.99
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  19. Men's 3-Eye Lug Handsewn Boat Shoe Men's 3-Eye Lug Handsewn Boat Shoe
    Men's 3-Eye Lug Handsewn Boat Shoe
    $119.99 $229.99
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  20. Men's 3-Eye Lug Handsewn Boat Shoe Men's 3-Eye Lug Handsewn Boat Shoe
    Men's 3-Eye Lug Handsewn Boat Shoe
    $119.99 $229.99
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  21. Men's Newmarket II Moc Toe Chukka
    Men's Newmarket II Moc Toe Chukka
    $99.99 $249.99
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  22. Men's GreenStride™ Atwells Ave Waterproof Chukka Boot Men's GreenStride™ Atwells Ave Waterproof Chukka Boot
    Men's GreenStride™ Atwells Ave Waterproof Chukka Boot
    $279.99
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  23. Men's Redwood Falls Waterproof Boot Men's Redwood Falls Waterproof Boot
    Men's Redwood Falls Waterproof Boot
    $279.99
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  24. Men's Atwells Ave Waterproof Boot Men's Atwells Ave Waterproof Boot
    Men's Atwells Ave Waterproof Boot
    $269.99
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  25. Men's 6-Inch Alburn Boot Men's 6-Inch Alburn Boot
    Men's 6-Inch Alburn Boot
    $119.99 $269.99
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  26. Men's Pro Radius Alloy Safety-Toe Work Boots Men's Pro Radius Alloy Safety-Toe Work Boots
    Men's Pro Radius Alloy Safety-Toe Work Boots
    $99.99 $249.99
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  27. PRO Cotton Core Logo T-Shirt PRO Cotton Core Logo T-Shirt
    PRO Cotton Core Logo T-Shirt
    $19.99 $44.99
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  28. Men's Atwells Ave Waterproof Boots Men's Atwells Ave Waterproof Boots
    Men's Atwells Ave Waterproof Boots
    $129.99 $269.99
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  29. Men's Bradstreet Plain-Toe Oxford Shoe Men's Bradstreet Plain-Toe Oxford Shoe
    Men's Bradstreet Plain-Toe Oxford Shoe
    $79.99 $219.99
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  30. Men's Cedar Bay Boat Shoe Men's Cedar Bay Boat Shoe
    Men's Cedar Bay Boat Shoe
    $229.99
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  31. Men’s Garrison Trail Hiking Sneakers Men’s Garrison Trail Hiking Sneakers
    Men’s Garrison Trail Hiking Sneakers
    $109.99 $199.99
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  32. Men’s Garrison Trail WP Mid Hiker Boots Men’s Garrison Trail WP Mid Hiker Boots
    Men’s Garrison Trail WP Mid Hiker Boots
    $129.99 $259.99
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  33. Men’s Garrison Trail Low AC Hiking Sneakers Men’s Garrison Trail Low AC Hiking Sneakers
    Men’s Garrison Trail Low AC Hiking Sneakers
    $109.99 $199.99
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  34. Men’s Short-Sleeve Shirt with TimberChill™ Climate-Control Technology Fabric
    Men’s Short-Sleeve Shirt with TimberChill™ Climate-Control Technology Fabric
    $59.99 $99.99
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  35. Men’s Short-Sleeve Shirt with TimberChill™ Climate-Control Technology Fabric Men’s Short-Sleeve Shirt with TimberChill™ Climate-Control Technology Fabric
    Men’s Short-Sleeve Shirt with TimberChill™ Climate-Control Technology Fabric
    $59.99 $99.99
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  36. Men's Summer Logo T-Shirt Men's Summer Logo T-Shirt
    Men's Summer Logo T-Shirt
    $39.99 $59.99
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  37. Men’s Printed Trail Shorts Men’s Printed Trail Shorts
    Men’s Printed Trail Shorts
    $49.99 $99.99
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  38. Men’s Printed Packable Anorak Men’s Printed Packable Anorak
    Men’s Printed Packable Anorak
    $79.99 $149.99
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  39. Lovell Lake Slim-Fit Stretch Jogger Pant Lovell Lake Slim-Fit Stretch Jogger Pant
    Lovell Lake Slim-Fit Stretch Jogger Pant
    $49.99 $139.99
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Find your favourite Men's Timberland apparel, footwear and accessories at a discounted price in our men's sale collection. Explore our popular range of footwear like our Men's Premium 6-Inch Boots or our Men's Boat Shoes at a discounted price. Style a complete Timberland look by browsing our Men's Sale Clothing for Tees, Jackets, Joggers and more. Don't forget to check out our collection of Men's Accessories to complete your look from head to toe. Shopping for someone else? Browse our Women's Sale range and Kid's Sale collection. Planning to shop our Black Friday sale? Find your favourite boots and clothing on sale before anyone by signing up for updates! Browse our Guide to Black Friday for everything you need to know about shopping in store or online with Timberland during one of the busiest weekends of the year. With free shipping and Afterpay options available, shop Timberland Men's Sale online today.