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Items 61-114 of 114

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  1. Men's Winsor Park Chukka Men's Winsor Park Chukka
    Men's Winsor Park Chukka
    $179.99 $259.99
    Add to List View
  2. Men's Basic Oxford Men's Basic Oxford
    Men's Basic Oxford
    $159.99 $239.99
    Add to List View
  3. Men's Mt. Maddsen Waterproof Mid Hiking Boot Men's Mt. Maddsen Waterproof Mid Hiking Boot
    Men's Mt. Maddsen Waterproof Mid Hiking Boot
    $199.99 $299.99
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  4. 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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  5. 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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  6. 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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  7. Men's Killington Low Lace-Up Sneaker Men's Killington Low Lace-Up Sneaker
    Men's Killington Low Lace-Up Sneaker
    $124.99 $179.99
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  8. Men's Killington Low Lace-Up Sneaker Men's Killington Low Lace-Up Sneaker
    Men's Killington Low Lace-Up Sneaker
    $124.99 $179.99
    Add to List View
  9. 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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  10. Men's Davis Square Chukka Men's Davis Square Chukka
    Men's Davis Square Chukka
    $149.99 $219.99
    Add to List View
  11. Men's Winsor Park Trainer Men's Winsor Park Trainer
    Men's Winsor Park Trainer
    $159.99 $229.99
    Add to List View
  12. Men's Cedar Bay Boat Shoe Men's Cedar Bay Boat Shoe
    Men's Cedar Bay Boat Shoe
    $149.99 $229.99
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  13. Men's Cedar Bay Boat Shoe Men's Cedar Bay Boat Shoe
    Men's Cedar Bay Boat Shoe
    $149.99 $229.99
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  14. Men's Seneca Bay Low Lace-Up Sneaker Men's Seneca Bay Low Lace-Up Sneaker
    Men's Seneca Bay Low Lace-Up Sneaker
    $109.99 $169.99
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  15. 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
    $219.99 $319.99
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  16. Men's Winsor Park Trainer Men's Winsor Park Trainer
    Men's Winsor Park Trainer
    $159.99 $229.99
    Add to List View
  17. Men's Mt. Maddsen Waterproof Low Hiker Boot Men's Mt. Maddsen Waterproof Low Hiker Boot
    Men's Mt. Maddsen Waterproof Low Hiker Boot
    $149.99 $219.99
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  18. 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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  19. 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
    Add to List View
  20. 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
    Add to List View
  21. 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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  22. 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
    Add to List View
  23. 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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  24. 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
  25. Men's Original 6-Inch Boot Men's Original 6-Inch Boot
    Men's Original 6-Inch Boot
    $129.99 $319.99
    Add to List View
  26. Men's Atwells Ave Waterproof Boot Men's Atwells Ave Waterproof Boot
    Men's Atwells Ave Waterproof Boot
    $129.99 $269.99
    Add to List View
  27. Men's Westmore Moc-Toe Chukka Men's Westmore Moc-Toe Chukka
    Men's Westmore Moc-Toe Chukka
    $99.99 $269.99
    Add to List View
  28. 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
    Add to List View
  29. 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
    Add to List View
  30. 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
  31. 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
    Add to List View
  32. 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
    Add to List View
  33. Men's Cedar Bay Boat Shoe Men's Cedar Bay Boat Shoe
    Men's Cedar Bay Boat Shoe
    $229.99
    Add to List View
  34. 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
  35. Men's Waterproof Field Boot Men's Waterproof Field Boot
    Men's Waterproof Field Boot
    $179.99 $259.99
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  36. Men's 3-Eye Lug Handsewn Boat Shoe Men's 3-Eye Lug Handsewn Boat Shoe
    Men's 3-Eye Lug Handsewn Boat Shoe
    $129.99 $249.99
    Add to List View
  37. Men's Euro Hiker Boot Men's Euro Hiker Boot
    Men's Euro Hiker Boot
    $179.99 $269.99
    Add to List View
  38. Men's Waterproof Field Boot Men's Waterproof Field Boot
    Men's Waterproof Field Boot
    $179.99 $259.99
    Add to List View
  39. Men's Westmore Chukka Men's Westmore Chukka
    Men's Westmore Chukka
    $179.99 $269.99
    Add to List View
  40. Men's Timberland® C.F. Stead™ Indigo Suede Euro Hiker Boot Men's Timberland® C.F. Stead™ Indigo Suede Euro Hiker Boot
    Men's Timberland® C.F. Stead™ Indigo Suede Euro Hiker Boot
    $179.99 $269.99
    Add to List View
  41. Men's Classic Boat Shoe Men's Classic Boat Shoe
    Men's Classic Boat Shoe
    $119.99 $199.99
    Add to List View
  42. Redwood Falls Waterproof Redwood Falls Waterproof
    Redwood Falls Waterproof
    $199.99 $299.99
    Add to List View
  43. Men's Timberland® C.F. Stead™ Indigo Suede 3-Eye Lug Handsewn Boat Shoe Men's Timberland® C.F. Stead™ Indigo Suede 3-Eye Lug Handsewn Boat Shoe
    Men's Timberland® C.F. Stead™ Indigo Suede 3-Eye Lug Handsewn Boat Shoe
    $169.99 $249.99
    Add to List View
  44. 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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  45. Men's Maple Grove Chukka Men's Maple Grove Chukka
    Men's Maple Grove Chukka
    $179.99 $259.99
    Add to List View
  46. Men's Atwells Ave Waterproof Boot Men's Atwells Ave Waterproof Boot
    Men's Atwells Ave Waterproof Boot
    $269.99
    Add to List View
  47. Men's Newmarket II Boot Men's Newmarket II Boot
    Men's Newmarket II Boot
    $159.99 $329.99
    Add to List View
  48. Men's Attleboro Mid Lace-Up Chukka Men's Attleboro Mid Lace-Up Chukka
    Men's Attleboro Mid Lace-Up Chukka
    $299.99
    Add to List View
  49. 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
    Add to List View
  50. Men's Atwell Ave Chelsea Boot Men's Atwell Ave Chelsea Boot
    Men's Atwell Ave Chelsea Boot
    $99.99 $259.99
    Add to List View
  51. Men's Redwood Falls Waterproof Boot Men's Redwood Falls Waterproof Boot
    Men's Redwood Falls Waterproof Boot
    $299.99
    Add to List View
  52. 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
    Add to List View
  53. Men's Newmarket II Boot Men's Newmarket II Boot
    Men's Newmarket II Boot
    $159.99 $329.99
    Add to List View
  54. 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
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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.