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Items 121-180 of 244

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  1. Men's Seneca Bay Sneaker Men's Seneca Bay Sneaker
    Men's Seneca Bay Sneaker
    $149.99 $219.99
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  2. Men's Maple Grove Low Lace-Up Sneaker Men's Maple Grove Low Lace-Up Sneaker
    Men's Maple Grove Low Lace-Up Sneaker
    $159.99 $239.99
    Add to List View
  3. Men's Winsor Park Trainer Men's Winsor Park Trainer
    Men's Winsor Park Trainer
    $159.99 $229.99
    Add to List View
  4. Men's Winsor Park Trainer Men's Winsor Park Trainer
    Men's Winsor Park Trainer
    $159.99 $229.99
    Add to List View
  5. PRO Performance Baseball Cap PRO Performance Baseball Cap
    PRO Performance Baseball Cap
    $19.99 $29.99
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  6. PRO Performance Baseball Cap PRO Performance Baseball Cap
    PRO Performance Baseball Cap
    $19.99 $29.99
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  7. Men's Redwood Falls Waterproof Chukka Boot Men's Redwood Falls Waterproof Chukka Boot
    Men's Redwood Falls Waterproof Chukka Boot
    $189.99 $279.99
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  8. Newmarket Village Ankle Socks 3-Pack Newmarket Village Ankle Socks 3-Pack
    Newmarket Village Ankle Socks 3-Pack
    $19.99 $29.99
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  9. Men's Attleboro Mid Lace-Up Chukka Men's Attleboro Mid Lace-Up Chukka
    Men's Attleboro Mid Lace-Up Chukka
    $199.99 $299.99
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  10. Denim Cap with Faux Suede Brim Denim Cap with Faux Suede Brim
    Denim Cap with Faux Suede Brim
    $39.99 $59.99
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  11. Vented Cap Vented Cap
    Vented Cap
    $44.99 $69.99
    Add to List View
  12. Men's Arbor Road 6-Inch Waterproof Boot Men's Arbor Road 6-Inch Waterproof Boot
    Men's Arbor Road 6-Inch Waterproof Boot
    $229.99 $329.99
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  13. Men's Arbor Road 6-Inch Waterproof Boot Men's Arbor Road 6-Inch Waterproof Boot
    Men's Arbor Road 6-Inch Waterproof Boot
    $229.99 $329.99
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  14. Men's Attleboro 6-Inch Boot Men's Attleboro 6-Inch Boot
    Men's Attleboro 6-Inch Boot
    $199.99 $299.99
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  15. Men's Arbor Road Waterproof Chukka Men's Arbor Road Waterproof Chukka
    Men's Arbor Road Waterproof Chukka
    $199.99 $299.99
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  16. Men's Arbor Road Waterproof Chukka Men's Arbor Road Waterproof Chukka
    Men's Arbor Road Waterproof Chukka
    $199.99 $299.99
    Add to List View
  17. Men's Winsor Park Chukka Men's Winsor Park Chukka
    Men's Winsor Park Chukka
    $179.99 $259.99
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  18. Men's Winsor Park Chukka Men's Winsor Park Chukka
    Men's Winsor Park Chukka
    $179.99 $259.99
    Add to List View
  19. Men's Mt. Maddsen Mid Lace-Up Hiking Boot Men's Mt. Maddsen Mid Lace-Up Hiking Boot
    Men's Mt. Maddsen Mid Lace-Up Hiking Boot
    $179.99 $259.99
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  20. Men's Mt. Maddsen Mid Lace-Up Hiking Boot Men's Mt. Maddsen Mid Lace-Up Hiking Boot
    Men's Mt. Maddsen Mid Lace-Up Hiking Boot
    $179.99 $259.99
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  21. Men's Garment Dye Quarter-Zip Sweatshirt Men's Garment Dye Quarter-Zip Sweatshirt
    Men's Garment Dye Quarter-Zip Sweatshirt
    $99.99 $149.99
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  22. Men's Merrymack River Chest Pocket T-Shirt Men's Merrymack River Chest Pocket T-Shirt
    Men's Merrymack River Chest Pocket T-Shirt
    $44.99 $69.99
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  23. Men's Short Sleeve Logo Graphic T-Shirt Men's Short Sleeve Logo Graphic T-Shirt
    Men's Short Sleeve Logo Graphic T-Shirt
    $44.99 $69.99
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  24. Men's Merrymack River Chest Pocket T-Shirt Men's Merrymack River Chest Pocket T-Shirt
    Men's Merrymack River Chest Pocket T-Shirt
    $44.99 $69.99
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  25. Men's Twill Cargo Pant Men's Twill Cargo Pant
    Men's Twill Cargo Pant
    $99.99 $149.99
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  26. Men's Washed Canvas Stretch Carpenter Pant Men's Washed Canvas Stretch Carpenter Pant
    Men's Washed Canvas Stretch Carpenter Pant
    $109.99 $159.99
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  27. Twill Cargo Shorts Twill Cargo Shorts
    Twill Cargo Shorts
    $79.99 $119.99
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  28. Twill Cargo Shorts Twill Cargo Shorts
    Twill Cargo Shorts
    $79.99 $119.99
    Add to List View
  29. Outdoor Utility Shorts Outdoor Utility Shorts
    Outdoor Utility Shorts
    $59.99 $109.99
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  30. Outdoor Utility Shorts Outdoor Utility Shorts
    Outdoor Utility Shorts
    $59.99 $109.99
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  31. Men's 50th Anniversary Edition 6-Inch Boot Men's 50th Anniversary Edition 6-Inch Boot
    Men's 50th Anniversary Edition 6-Inch Boot
    $159.99 $349.99
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  32. Men's 50th Anniversary Edition 6-Inch Boot Men's 50th Anniversary Edition 6-Inch Boot
    Men's 50th Anniversary Edition 6-Inch Boot
    $159.99 $349.99
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  33. Men's 50th Anniversary Edition 6-Inch Boot Men's 50th Anniversary Edition 6-Inch Boot
    Men's 50th Anniversary Edition 6-Inch Boot
    $139.99 $349.99
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  34. Men's 50th Anniversary Edition 6-Inch Boot Men's 50th Anniversary Edition 6-Inch Boot
    Men's 50th Anniversary Edition 6-Inch Boot
    $139.99 $349.99
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  35. Men's Original 6-Inch Boot Men's Original 6-Inch Boot
    Men's Original 6-Inch Boot
    $209.99 $319.99
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  36. Men's Heritage 6-Inch Waterproof Boots Men's Heritage 6-Inch Waterproof Boots
    Men's Heritage 6-Inch Waterproof Boots
    $199.99 $329.99
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  37. Men's Premium 6-Inch Waterproof Boot Men's Premium 6-Inch Waterproof Boot
    Men's Premium 6-Inch Waterproof Boot
    $229.99 $349.99
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  38. Men's Original 6-Inch Boot Men's Original 6-Inch Boot
    Men's Original 6-Inch Boot
    $129.99 $319.99
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  39. Men's Atwells Ave Waterproof Boot Men's Atwells Ave Waterproof Boot
    Men's Atwells Ave Waterproof Boot
    $129.99 $269.99
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  40. Men's Premium 6-Inch Waterproof Boot Men's Premium 6-Inch Waterproof Boot
    Men's Premium 6-Inch Waterproof Boot
    $199.99 $349.99
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  41. Men's Westmore Moc-Toe Chukka Men's Westmore Moc-Toe Chukka
    Men's Westmore Moc-Toe Chukka
    $99.99 $269.99
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  42. Men's 3-Eye Lug Handsewn Boat Shoe Men's 3-Eye Lug Handsewn Boat Shoe
    Men's 3-Eye Lug Handsewn Boat Shoe
    $139.99 $249.99
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  43. Men's Pro Radius Work Sneaker Men's Pro Radius Work Sneaker
    Men's Pro Radius Work Sneaker
    $129.99 $239.99
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  44. Men's Pro Radius Work Sneaker Men's Pro Radius Work Sneaker
    Men's Pro Radius Work Sneaker
    $129.99 $239.99
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  45. Men's 3-Eye Lug Handsewn Boat Shoe Men's 3-Eye Lug Handsewn Boat Shoe
    Men's 3-Eye Lug Handsewn Boat Shoe
    $139.99 $249.99
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  46. Men's Washed Canvas Jacket Men's Washed Canvas Jacket
    Men's Washed Canvas Jacket
    $149.99 $219.99
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  47. Men's Washed Canvas Jacket Men's Washed Canvas Jacket
    Men's Washed Canvas Jacket
    $149.99 $219.99
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  48. Water Repellent Outdoor Cargo Shorts Water Repellent Outdoor Cargo Shorts
    Water Repellent Outdoor Cargo Shorts
    $59.99 $119.99
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  49. Water Repellent Outdoor Cargo Shorts Water Repellent Outdoor Cargo Shorts
    Water Repellent Outdoor Cargo Shorts
    $59.99 $119.99
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  50. Twill Cargo Shorts Twill Cargo Shorts
    Twill Cargo Shorts
    $79.99 $119.99
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  51. Men's Utility Mixed Media Overshirt Men's Utility Mixed Media Overshirt
    Men's Utility Mixed Media Overshirt
    $99.99 $149.99
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  52. 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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  53. Chest Logo Jersey Crew Tee Chest Logo Jersey Crew Tee
    Chest Logo Jersey Crew Tee
    $39.99 $59.99
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  54. PRO Base Plate Short Sleeve Graphic Tee PRO Base Plate Short Sleeve Graphic Tee
    PRO Base Plate Short Sleeve Graphic Tee
    $29.99 $44.99
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  55. PRO Base Plate Short Sleeve Graphic Tee PRO Base Plate Short Sleeve Graphic Tee
    PRO Base Plate Short Sleeve Graphic Tee
    $29.99 $44.99
    Add to List View
  56. Men's Premium 6-Inch Waterproof Boot Men's Premium 6-Inch Waterproof Boot
    Men's Premium 6-Inch Waterproof Boot
    $229.99 $349.99
    Add to List View
  57. 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
    Add to List View
  58. Pro Tempe Jogger Pant Pro Tempe Jogger Pant
    Pro Tempe Jogger Pant
    $39.99 $89.99
    Add to List View
  59. Pro Tempe Jogger Pant Pro Tempe Jogger Pant
    Pro Tempe Jogger Pant
    $39.99 $89.99
    Add to List View
  60. 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
    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.