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  1. Men
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Size US Mens
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Items 1-59 of 76

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  1. 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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  2. 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
    Add to List View
  3. Men's 6-inch Lace-Up Boot Men's 6-inch Lace-Up Boot
    Men's 6-inch Lace-Up Boot
    $179.99 $279.99
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  4. Men's 6-inch Lace-Up Boot Men's 6-inch Lace-Up Boot
    Men's 6-inch Lace-Up Boot
    $179.99 $279.99
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  5. 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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  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 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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  8. 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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  9. 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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  10. 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
  11. Redwood Falls Waterproof Redwood Falls Waterproof
    Redwood Falls Waterproof
    $199.99 $299.99
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  12. Men's Winsor Park Chukka Men's Winsor Park Chukka
    Men's Winsor Park Chukka
    $179.99 $259.99
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  13. Men's Winsor Park Chukka Men's Winsor Park Chukka
    Men's Winsor Park Chukka
    $179.99 $259.99
    Add to List View
  14. Men's 6-Inch Alburn Boot Men's 6-Inch Alburn Boot
    Men's 6-Inch Alburn Boot
    $249.99 $279.99
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  15. Men's 6-Inch Alburn Boot Men's 6-Inch Alburn Boot
    Men's 6-Inch Alburn Boot
    $249.99 $279.99
    Add to List View
  16. Men's Maple Grove Chukka Men's Maple Grove Chukka
    Men's Maple Grove Chukka
    $179.99 $259.99
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  17. Men's 6-Inch Premium Waterproof Boot Men's 6-Inch Premium Waterproof Boot
    Men's 6-Inch Premium Waterproof Boot
    $229.99 $329.99
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  18. Men's Pro Hypercharge 6-Inch Composite Toe Waterproof Work Boot Men's Pro Hypercharge 6-Inch Composite Toe Waterproof Work Boot
    Men's Pro Hypercharge 6-Inch Composite Toe Waterproof Work Boot
    $179.99 $299.99
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  19. Men's Pro Hypercharge 6-Inch Composite Toe Waterproof Work Boot Men's Pro Hypercharge 6-Inch Composite Toe Waterproof Work Boot
    Men's Pro Hypercharge 6-Inch Composite Toe Waterproof Work Boot
    $179.99 $299.99
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  20. 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
  21. 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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  22. Men's Original 6-Inch Boot Men's Original 6-Inch Boot
    Men's Original 6-Inch Boot
    $189.99 $319.99
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  23. Men's Westmore Moc-Toe Chukka Men's Westmore Moc-Toe Chukka
    Men's Westmore Moc-Toe Chukka
    $139.99 $269.99
    Add to List View
  24. Men's Waterproof Field Boot Men's Waterproof Field Boot
    Men's Waterproof Field Boot
    $179.99 $259.99
    Add to List View
  25. 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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  26. 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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  27. 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
  28. Men's Premium 6-Inch Waterproof Boot Men's Premium 6-Inch Waterproof Boot
    Men's Premium 6-Inch Waterproof Boot
    $189.99 $349.99
    Add to List View
  29. Tree Logo Leather Belt Tree Logo Leather Belt
    Tree Logo Leather Belt
    $54.99 $99.99
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  30. 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
  31. Men's Westmore Chukka Men's Westmore Chukka
    Men's Westmore Chukka
    $179.99 $269.99
    Add to List View
  32. Men's Waterproof Field Boot Men's Waterproof Field Boot
    Men's Waterproof Field Boot
    $179.99 $259.99
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  33. 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
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  34. 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
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  35. Men's Westmore Chukka Men's Westmore Chukka
    Men's Westmore Chukka
    $179.99 $269.99
    Add to List View
  36. 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
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  37. Men's Westmore Chukka Men's Westmore Chukka
    Men's Westmore Chukka
    $179.99 $269.99
    Add to List View
  38. 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
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  39. Men's Premium Chukka Men's Premium Chukka
    Men's Premium Chukka
    $209.99 $329.99
    Add to List View
  40. Men's Classic 6-Inch Waterproof Boot Men's Classic 6-Inch Waterproof Boot
    Men's Classic 6-Inch Waterproof Boot
    $189.99 $279.99
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  41. Men's 3-Eye Lug Handsewn Boat Shoe Men's 3-Eye Lug Handsewn Boat Shoe
    Men's 3-Eye Lug Handsewn Boat Shoe
    $174.99 $249.99
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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
    $174.99 $249.99
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  43. Men's Newmarket II Boot Men's Newmarket II Boot
    Men's Newmarket II Boot
    $229.99 $329.99
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  44. Men's Newmarket II Boot Men's Newmarket II Boot
    Men's Newmarket II Boot
    $229.99 $329.99
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  45. Men's Atwells Ave Waterproof Boots Men's Atwells Ave Waterproof Boots
    Men's Atwells Ave Waterproof Boots
    $179.99 $269.99
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  46. Men's Atwell Ave Chelsea Boot Men's Atwell Ave Chelsea Boot
    Men's Atwell Ave Chelsea Boot
    $149.99 $259.99
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  47. Men's Newmarket II Moc Toe Chukka
    Men's Newmarket II Moc Toe Chukka
    $99.99 $249.99
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  48. 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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  49. Men's Classic Boat Shoe Men's Classic Boat Shoe
    Men's Classic Boat Shoe
    $119.99 $199.99
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  50. Men's GreenStride™ Atwells Ave Waterproof Chukka Boot Men's GreenStride™ Atwells Ave Waterproof Chukka Boot
    Men's GreenStride™ Atwells Ave Waterproof Chukka Boot
    $179.99 $259.99
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  51. 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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  52. Men's Newmarket II 6-Inch Boot Men's Newmarket II 6-Inch Boot
    Men's Newmarket II 6-Inch Boot
    $74.99 $259.99
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  53. Men's Killington Trekker Low Men's Killington Trekker Low
    Men's Killington Trekker Low
    $89.99 $219.99
    Add to List View
  54. Men's 6-Inch Alburn Boot Men's 6-Inch Alburn Boot
    Men's 6-Inch Alburn Boot
    $119.99 $269.99
    Add to List View
  55. 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
  56. 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
  57. Men's Classic 6-Inch Waterproof Boot Men's Classic 6-Inch Waterproof Boot
    Men's Classic 6-Inch Waterproof Boot
    $159.99 $279.99
    Add to List View
  58. Men's Premium 6-Inch Waterproof Boot Men's Premium 6-Inch Waterproof Boot
    Men's Premium 6-Inch Waterproof Boot
    $179.99 $349.99
    Add to List View
  59. Men's Classic Waterproof Chukka Men's Classic Waterproof Chukka
    Men's Classic Waterproof Chukka
    $94.99 $279.99
    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.