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Items 241-300 of 301

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  1. Men's Seaton Bay Cross-Strap Sandal Men's Seaton Bay Cross-Strap Sandal
    Men's Seaton Bay Cross-Strap Sandal
    $149.99
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  2. Men's Euro Hiker Mid Lace-Up With Gore-Tex Bootie Men's Euro Hiker Mid Lace-Up With Gore-Tex Bootie
    Men's Euro Hiker Mid Lace-Up With Gore-Tex Bootie
    $299.99
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  3. Men's 3-Eye Lug Handsewn Boat Shoe Men's 3-Eye Lug Handsewn Boat Shoe
    Men's 3-Eye Lug Handsewn Boat Shoe
    $99.99 $249.99
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  4. 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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  5. Unisex Tokyo Design Collective Front Snap Sweat Unisex Tokyo Design Collective Front Snap Sweat
    Unisex Tokyo Design Collective Front Snap Sweat
    $99.99 $159.99
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  6. Unisex Tokyo Design Collective Front Snap Sweat Unisex Tokyo Design Collective Front Snap Sweat
    Unisex Tokyo Design Collective Front Snap Sweat
    $99.99 $159.99
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  7. Men's Westmore Chukka Men's Westmore Chukka
    Men's Westmore Chukka
    $179.99 $269.99
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  8. EZ LOUNGE SLIP-ON
    EZ LOUNGE SLIP-ON
    $39.99 $179.99
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  9. Men's Classic Waterproof Chukka Men's Classic Waterproof Chukka
    Men's Classic Waterproof Chukka
    $94.99 $279.99
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  10. Unisex Tokyo Design Collective Half Zip Sweat Unisex Tokyo Design Collective Half Zip Sweat
    Unisex Tokyo Design Collective Half Zip Sweat
    $99.99 $159.99
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  11. Unisex Tokyo Design Collection Anorak Unisex Tokyo Design Collection Anorak
    Unisex Tokyo Design Collection Anorak
    $139.99 $199.99
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  12. Unisex Tokyo Design Collective Rugby Shirt Unisex Tokyo Design Collective Rugby Shirt
    Unisex Tokyo Design Collective Rugby Shirt
    $95.99 $139.99
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  13. Men’s Printed Packable Anorak Men’s Printed Packable Anorak
    Men’s Printed Packable Anorak
    $79.99 $149.99
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  14. Men's Westmore Chukka Men's Westmore Chukka
    Men's Westmore Chukka
    $179.99 $269.99
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  15. Men's Polartec® Logo Crewneck Sweatshirt Men's Polartec® Logo Crewneck Sweatshirt
    Men's Polartec® Logo Crewneck Sweatshirt
    $99.99 $149.99
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  16. Unisex Tokyo Design Collective Long Sleeve Shirt Unisex Tokyo Design Collective Long Sleeve Shirt
    Unisex Tokyo Design Collective Long Sleeve Shirt
    $99.99 $159.99
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  17. 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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  18. Men's Ski School Water Repellent Puffer Jacket Men's Ski School Water Repellent Puffer Jacket
    Men's Ski School Water Repellent Puffer Jacket
    $249.99 $359.99
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  19. 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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  20. Unisex Tokyo Design Collection Anorak Unisex Tokyo Design Collection Anorak
    Unisex Tokyo Design Collection Anorak
    $139.99 $199.99
    Add to List View
  21. Unisex Tokyo Design Collective Corduroy Shorts Unisex Tokyo Design Collective Corduroy Shorts
    Unisex Tokyo Design Collective Corduroy Shorts
    $79.99 $119.99
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  22. 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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  23. 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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  24. Unisex Tokyo Design Collective Corduroy Shorts Unisex Tokyo Design Collective Corduroy Shorts
    Unisex Tokyo Design Collective Corduroy Shorts
    $79.99 $119.99
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  25. 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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  26. WOVEN LOGO LOW PROFILE DAD CAP
    WOVEN LOGO LOW PROFILE DAD CAP
    $14.99 $29.99
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  27. Unisex Tokyo Design Collection Cropped Pants Unisex Tokyo Design Collection Cropped Pants
    Unisex Tokyo Design Collection Cropped Pants
    $79.99 $124.99
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  28. Unisex Tokyo Design Collective Long Sleeve Shirt Unisex Tokyo Design Collective Long Sleeve Shirt
    Unisex Tokyo Design Collective Long Sleeve Shirt
    $99.99 $159.99
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  29. 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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  30. Unisex Tokyo Design Collection Cropped Pants Unisex Tokyo Design Collection Cropped Pants
    Unisex Tokyo Design Collection Cropped Pants
    $79.99 $124.99
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  31. Men's Killington Trekker Low Men's Killington Trekker Low
    Men's Killington Trekker Low
    $89.99 $219.99
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  32. Casual Sweatpants Casual Sweatpants
    Casual Sweatpants
    $39.99 $99.99
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  33. SENECA BAY SNEAKER BOOT
    SENECA BAY SNEAKER BOOT
    $59.99 $199.99
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  34. Ultrastretch Cargo Pant Ultrastretch Cargo Pant
    Ultrastretch Cargo Pant
    $49.99 $139.99
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  35. 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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  36. Water Repellent Jogger Water Repellent Jogger
    Water Repellent Jogger
    $69.99 $149.99
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  37. DWR Windbreaker Jogger Pant DWR Windbreaker Jogger Pant
    DWR Windbreaker Jogger Pant
    $39.99 $139.99
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  38. 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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  39. Casual Sweatpants Casual Sweatpants
    Casual Sweatpants
    $39.99 $99.99
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  40. Water Repellent Cargo Trousers Water Repellent Cargo Trousers
    Water Repellent Cargo Trousers
    $59.99 $149.99
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  41. Ultrastretch Cargo Pant Ultrastretch Cargo Pant
    Ultrastretch Cargo Pant
    $29.99 $139.99
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  42. Men’s Printed Trail Shorts Men’s Printed Trail Shorts
    Men’s Printed Trail Shorts
    $49.99 $99.99
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  43. Carrier Tee Carrier Tee
    Carrier Tee
    $19.99 $59.99
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  44. Men's Short-Sleeve Merrymack Pocket T-Shirt Men's Short-Sleeve Merrymack Pocket T-Shirt
    Men's Short-Sleeve Merrymack Pocket T-Shirt
    $39.99 $79.99
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  45. 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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  46. 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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  47. Unisex Short Sleeve Heavyweight Boots Badge Tee Unisex Short Sleeve Heavyweight Boots Badge Tee
    Unisex Short Sleeve Heavyweight Boots Badge Tee
    $39.99 $69.99
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  48. Men's Redwood Falls Waterproof Boot Men's Redwood Falls Waterproof Boot
    Men's Redwood Falls Waterproof Boot
    $299.99
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  49. Men's Short Sleeve T-Shirt with TimberCHILL™ Technology Men's Short Sleeve T-Shirt with TimberCHILL™ Technology
    Men's Short Sleeve T-Shirt with TimberCHILL™ Technology
    $29.99 $79.99
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  50. 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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  51. Short Sleeve Original Boot Graphic Tee Short Sleeve Original Boot Graphic Tee
    Short Sleeve Original Boot Graphic Tee
    $29.99 $59.99
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  52. Men's Newmarket II Boot Men's Newmarket II Boot
    Men's Newmarket II Boot
    $159.99 $329.99
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  53. Men's Classic 6-Inch Waterproof Boot Men's Classic 6-Inch Waterproof Boot
    Men's Classic 6-Inch Waterproof Boot
    $139.99 $279.99
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  54. 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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  55. 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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  56. Men’s Timberland® C.F. Stead™ Indigo Suede Heritage 6-Inch Boot Men’s Timberland® C.F. Stead™ Indigo Suede Heritage 6-Inch Boot
    Men’s Timberland® C.F. Stead™ Indigo Suede Heritage 6-Inch Boot
    $299.99 $329.99
    Add to List View
  57. Men's Redwood Falls Waterproof Boot Men's Redwood Falls Waterproof Boot
    Men's Redwood Falls Waterproof Boot
    $279.99
    Add to List View
  58. TREE VAULT 6 INCH BOOT WP
    TREE VAULT 6 INCH BOOT WP
    $95.99 $299.99
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  59. 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
    Add to List View
  60. Men's Pro Ballast 6-Inch Steel Toe Work Boot Men's Pro Ballast 6-Inch Steel Toe Work Boot
    Men's Pro Ballast 6-Inch Steel Toe Work Boot
    $119.99 $259.99
    Add to List View
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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.