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Items 1-60 of 279

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  1. Men's 6-Inch Premium Waterproof Boot Men's 6-Inch Premium Waterproof Boot
    Men's 6-Inch Premium Waterproof Boot
    $329.99
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  2. Men's 6-Inch Premium Waterproof Boot Men's 6-Inch Premium Waterproof Boot
    Men's 6-Inch Premium Waterproof Boot
    $329.99
    Add to List View
  3. Men's 6-Inch Premium Waterproof Boot Men's 6-Inch Premium Waterproof Boot
    Men's 6-Inch Premium Waterproof Boot
    $329.99
    Add to List View
  4. Men's Earthkeeper® Original Leather 6-Inch Boot Men's Earthkeeper® Original Leather 6-Inch Boot
    Men's Earthkeeper® Original Leather 6-Inch Boot
    $319.99
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  5. Men's Classic 6-Inch Waterproof Boots Men's Classic 6-Inch Waterproof Boots
    Men's Classic 6-Inch Waterproof Boots
    $279.99
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  6. Mountain Graphic Short Sleeve T-Shirt Mountain Graphic Short Sleeve T-Shirt
    Mountain Graphic Short Sleeve T-Shirt
    $69.99
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  7. Graphic Loopback Hoodie Sweatshirt Graphic Loopback Hoodie Sweatshirt
    Graphic Loopback Hoodie Sweatshirt
    $149.99
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  8. Graphic Loopback Hoodie Sweatshirt Graphic Loopback Hoodie Sweatshirt
    Graphic Loopback Hoodie Sweatshirt
    $149.99
    Add to List View
  9. Benton Water-Resistant Shell Jacket Benton Water-Resistant Shell Jacket
    Benton Water-Resistant Shell Jacket
    $239.99
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  10. Denim Trucker Jacket Denim Trucker Jacket
    Denim Trucker Jacket
    $239.99
    Add to List View
  11. Men's Waterproof Field Boot Men's Waterproof Field Boot
    Men's Waterproof Field Boot
    $259.99
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  12. Men's Winsor Park Trainer Men's Winsor Park Trainer
    Men's Winsor Park Trainer
    $229.99
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  13. Men's Winsor Park Trainer Men's Winsor Park Trainer
    Men's Winsor Park Trainer
    $229.99
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  14. Men's Killington Low Lace-Up Sneaker Men's Killington Low Lace-Up Sneaker
    Men's Killington Low Lace-Up Sneaker
    $179.99
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  15. Men's Killington Low Lace-Up Sneaker Men's Killington Low Lace-Up Sneaker
    Men's Killington Low Lace-Up Sneaker
    $179.99
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  16. Graphic Logo Crewneck Sweatshirt Graphic Logo Crewneck Sweatshirt
    Graphic Logo Crewneck Sweatshirt
    $149.99
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  17. Graphic Logo Crewneck Sweatshirt Graphic Logo Crewneck Sweatshirt
    Graphic Logo Crewneck Sweatshirt
    $149.99
    Add to List View
  18. Wordmark Camo T-Shirt Wordmark Camo T-Shirt
    Wordmark Camo T-Shirt
    $69.99
    Add to List View
  19. Men’s Heritage 6-Inch Lace-Up Boot Men’s Heritage 6-Inch Lace-Up Boot
    Men’s Heritage 6-Inch Lace-Up Boot
    $329.99
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  20. Men’s Heritage 6-Inch Lace-Up Boot Men’s Heritage 6-Inch Lace-Up Boot
    Men’s Heritage 6-Inch Lace-Up Boot
    $329.99
    Add to List View
  21. Men’s Heritage 6-Inch Lace-Up Boot Men’s Heritage 6-Inch Lace-Up Boot
    Men’s Heritage 6-Inch Lace-Up Boot
    $329.99
    Add to List View
  22. Men's Classic 6-Inch Waterproof Boot Men's Classic 6-Inch Waterproof Boot
    Men's Classic 6-Inch Waterproof Boot
    $279.99
    Add to List View
  23. Men's Classic 6-Inch Waterproof Boot Men's Classic 6-Inch Waterproof Boot
    Men's Classic 6-Inch Waterproof Boot
    $279.99
    Add to List View
  24. Men's Icon Waterproof Chukka Boot Men's Icon Waterproof Chukka Boot
    Men's Icon Waterproof Chukka Boot
    $299.99
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  25. Men's Davis Square Chukka Men's Davis Square Chukka
    Men's Davis Square Chukka
    $219.99
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  26. Men's Seneca Bay Low Lace-Up Sneaker Men's Seneca Bay Low Lace-Up Sneaker
    Men's Seneca Bay Low Lace-Up Sneaker
    $169.99
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  27. Men's Crestfield Waterproof Sneaker Men's Crestfield Waterproof Sneaker
    Men's Crestfield Waterproof Sneaker
    $269.99
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  28. Men's Crestfield Waterproof Sneaker Men's Crestfield Waterproof Sneaker
    Men's Crestfield Waterproof Sneaker
    $269.99
    Add to List View
  29. Men's Motion Scramble Mid Lace-Up Waterproof Hiker Men's Motion Scramble Mid Lace-Up Waterproof Hiker
    Men's Motion Scramble Mid Lace-Up Waterproof Hiker
    $319.99
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  30. Men's Motion Scramble Mid Lace-Up Waterproof Hiker Men's Motion Scramble Mid Lace-Up Waterproof Hiker
    Men's Motion Scramble Mid Lace-Up Waterproof Hiker
    $319.99
    Add to List View
  31. Men's Motion Scramble Mid Lace-Up Waterproof Hiker Men's Motion Scramble Mid Lace-Up Waterproof Hiker
    Men's Motion Scramble Mid Lace-Up Waterproof Hiker
    $319.99
    Add to List View
  32. Men's Motion Scramble Low Lace-Up Waterproof Hiker Men's Motion Scramble Low Lace-Up Waterproof Hiker
    Men's Motion Scramble Low Lace-Up Waterproof Hiker
    $299.99
    Add to List View
  33. Men's Motion Scramble Low Lace-Up Waterproof Hiker Men's Motion Scramble Low Lace-Up Waterproof Hiker
    Men's Motion Scramble Low Lace-Up Waterproof Hiker
    $299.99
    Add to List View
  34. Denim Trucker Jacket Denim Trucker Jacket
    Denim Trucker Jacket
    $239.99
    Add to List View
  35. Durable Water-Repellent Bomber Jacket Durable Water-Repellent Bomber Jacket
    Durable Water-Repellent Bomber Jacket
    $239.99
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  36. Durable Water-Repellent Bomber Jacket Durable Water-Repellent Bomber Jacket
    Durable Water-Repellent Bomber Jacket
    $239.99
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  37. Polartec® Fleece Ultralight Packable Vest Polartec® Fleece Ultralight Packable Vest
    Polartec® Fleece Ultralight Packable Vest
    $189.99
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  38. Men's Washed Canvas Jacket Men's Washed Canvas Jacket
    Men's Washed Canvas Jacket
    $149.99 $219.99
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  39. Men's Washed Canvas Jacket Men's Washed Canvas Jacket
    Men's Washed Canvas Jacket
    $149.99 $219.99
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  40. Multi Purpose Short Sleeve Polo Shirt Multi Purpose Short Sleeve Polo Shirt
    Multi Purpose Short Sleeve Polo Shirt
    $99.99
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  41. Multi-Purpose Short Sleeve T-Shirt Multi-Purpose Short Sleeve T-Shirt
    Multi-Purpose Short Sleeve T-Shirt
    $69.99
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  42. Denim Pant With Refibra™ Technology Denim Pant With Refibra™ Technology
    Denim Pant With Refibra™ Technology
    $159.99
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  43. Denim Pant With Refibra™ Technology Denim Pant With Refibra™ Technology
    Denim Pant With Refibra™ Technology
    $159.99
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  44. Men's Classic 6-Inch Waterproof Boots Men's Classic 6-Inch Waterproof Boots
    Men's Classic 6-Inch Waterproof Boots
    $279.99
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  45. Men's Timberland® Heritage Black Pioneers 6-Inch Waterproof Boot Men's Timberland® Heritage Black Pioneers 6-Inch Waterproof Boot
    Men's Timberland® Heritage Black Pioneers 6-Inch Waterproof Boot
    $329.99
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  46. Men's Attleboro 6-Inch Boot Men's Attleboro 6-Inch Boot
    Men's Attleboro 6-Inch Boot
    $299.99
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  47. Men's Maple Grove Chukka Men's Maple Grove Chukka
    Men's Maple Grove Chukka
    $259.99
    Add to List View
  48. Men's Maple Grove Chukka Men's Maple Grove Chukka
    Men's Maple Grove Chukka
    $259.99
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  49. Men's Seneca Bay Sneaker Men's Seneca Bay Sneaker
    Men's Seneca Bay Sneaker
    $219.99
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  50. Men's Seneca Bay Sneaker Men's Seneca Bay Sneaker
    Men's Seneca Bay Sneaker
    $219.99
    Add to List View
  51. Men's Maple Grove Low Lace-Up Sneaker Men's Maple Grove Low Lace-Up Sneaker
    Men's Maple Grove Low Lace-Up Sneaker
    $239.99
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  52. Men's Maple Grove Low Lace-Up Sneaker Men's Maple Grove Low Lace-Up Sneaker
    Men's Maple Grove Low Lace-Up Sneaker
    $239.99
    Add to List View
  53. Workwear Label Loopback Crew Neck Workwear Label Loopback Crew Neck
    Workwear Label Loopback Crew Neck
    $129.99
    Add to List View
  54. Workwear Label Loopback Crew Neck Workwear Label Loopback Crew Neck
    Workwear Label Loopback Crew Neck
    $129.99
    Add to List View
  55. Millers River Pique Slim-Fit Polo Shirt Millers River Pique Slim-Fit Polo Shirt
    Millers River Pique Slim-Fit Polo Shirt
    $79.99
    Add to List View
  56. Millers River Pique Slim-Fit Polo Shirt Millers River Pique Slim-Fit Polo Shirt
    Millers River Pique Slim-Fit Polo Shirt
    $79.99
    Add to List View
  57. Millers River Pique Slim-Fit Polo Shirt Millers River Pique Slim-Fit Polo Shirt
    Millers River Pique Slim-Fit Polo Shirt
    $79.99
    Add to List View
  58. Multi-Purpose Short Sleeve T-Shirt Multi-Purpose Short Sleeve T-Shirt
    Multi-Purpose Short Sleeve T-Shirt
    $69.99
    Add to List View
  59. Multi-Purpose Short Sleeve T-Shirt Multi-Purpose Short Sleeve T-Shirt
    Multi-Purpose Short Sleeve T-Shirt
    $69.99
    Add to List View
  60. Waterproof Hooded Shell Waterproof Hooded Shell
    Waterproof Hooded Shell
    $219.99
    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.