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Category
  1. Boots
  2. Sneakers
  3. Shoes
  4. Hiking Boots & Shoes
  5. Boat Shoes & Sandals
  6. Chukka
Gender
  1. Men
Material
  1. Fabric
  2. Leather
  3. Mesh
  4. Nylon
  5. Suede
  6. Nubuck
Size
3/4
Size US Mens
6
7
7.5
8
8.5
9
10
11
12
13
14
15
Size EU
39
40
41
41.5
42
43
44
45
46
47.5
49
50
Size UK
5.5
6.5
7
7.5
8
8.5
9.5
10.5
11.5
12.5
13.5
14.5
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Items 61-120 of 132

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  1. Men's Crestfield Waterproof Sneaker Men's Crestfield Waterproof Sneaker
    Men's Crestfield Waterproof Sneaker
    $179.99 $269.99
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  2. Men's Crestfield Waterproof Sneaker Men's Crestfield Waterproof Sneaker
    Men's Crestfield Waterproof Sneaker
    $179.99 $269.99
    Add to List View
  3. Men's Westmore Chukka Men's Westmore Chukka
    Men's Westmore Chukka
    $179.99 $269.99
    Add to List View
  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
    Add to List View
  5. Men's Winsor Park Chukka Men's Winsor Park Chukka
    Men's Winsor Park Chukka
    $179.99 $259.99
    Add to List View
  6. Men's Winsor Park Chukka Men's Winsor Park Chukka
    Men's Winsor Park Chukka
    $179.99 $259.99
    Add to List View
  7. Men's Maple Grove Chukka Men's Maple Grove Chukka
    Men's Maple Grove Chukka
    $179.99 $259.99
    Add to List View
  8. Men's Waterproof Field Boot Men's Waterproof Field Boot
    Men's Waterproof Field Boot
    $179.99 $259.99
    Add to List View
  9. 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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  10. Men's Classic 6-Inch Waterproof Boot Men's Classic 6-Inch Waterproof Boot
    Men's Classic 6-Inch Waterproof Boot
    $179.99 $279.99
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  11. Men's Classic 6-Inch Waterproof Boot Men's Classic 6-Inch Waterproof Boot
    Men's Classic 6-Inch Waterproof Boot
    $179.99 $279.99
    Add to List View
  12. 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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  13. 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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  14. Men's Killington Low Lace-Up Sneaker Men's Killington Low Lace-Up Sneaker
    Men's Killington Low Lace-Up Sneaker
    $179.99
    Add to List View
  15. Men's Waterproof Field Boot Men's Waterproof Field Boot
    Men's Waterproof Field Boot
    $179.99 $259.99
    Add to List View
  16. Men's Westmore Chukka Men's Westmore Chukka
    Men's Westmore Chukka
    $179.99 $269.99
    Add to List View
  17. Men's Classic 6-Inch Waterproof Boots Men's Classic 6-Inch Waterproof Boots
    Men's Classic 6-Inch Waterproof Boots
    $189.99 $279.99
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  18. Men's Classic 6-Inch Waterproof Boots Men's Classic 6-Inch Waterproof Boots
    Men's Classic 6-Inch Waterproof Boots
    $189.99 $279.99
    Add to List View
  19. Men's GreenStride™ Atwells Ave Waterproof Chukka Boot Men's GreenStride™ Atwells Ave Waterproof Chukka Boot
    Men's GreenStride™ Atwells Ave Waterproof Chukka Boot
    $189.99 $279.99
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  20. Men's GreenStride™ Atwells Ave Waterproof Chukka Boot Men's GreenStride™ Atwells Ave Waterproof Chukka Boot
    Men's GreenStride™ Atwells Ave Waterproof Chukka Boot
    $189.99 $279.99
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  21. Men's Redwood Falls Waterproof Chukka Boot Men's Redwood Falls Waterproof Chukka Boot
    Men's Redwood Falls Waterproof Chukka Boot
    $195.99 $279.99
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  22. Men's 2-Eye Boat Shoe Men's 2-Eye Boat Shoe
    Men's 2-Eye Boat Shoe
    $199.99
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  23. Men's Icon Waterproof Chukka Boot Men's Icon Waterproof Chukka Boot
    Men's Icon Waterproof Chukka Boot
    $199.99 $299.99
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  24. Redwood Falls Waterproof Redwood Falls Waterproof
    Redwood Falls Waterproof
    $199.99 $299.99
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  25. 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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  26. 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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  27. 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
  28. Men's Attleboro 6-Inch Boot Men's Attleboro 6-Inch Boot
    Men's Attleboro 6-Inch Boot
    $199.99 $299.99
    Add to List View
  29. 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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  30. Men's Classic Leather Boat Shoe Men's Classic Leather Boat Shoe
    Men's Classic Leather Boat Shoe
    $199.99
    Add to List View
  31. Men's Classic Leather Boat Shoe Men's Classic Leather Boat Shoe
    Men's Classic Leather Boat Shoe
    $199.99
    Add to List View
  32. 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
  33. Men's Classic Leather Boat Shoe Men's Classic Leather Boat Shoe
    Men's Classic Leather Boat Shoe
    $199.99
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  34. 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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  35. Men’s Heritage 6-Inch Lace-Up Boot Men’s Heritage 6-Inch Lace-Up Boot
    Men’s Heritage 6-Inch Lace-Up Boot
    $199.99 $329.99
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  36. 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
    $199.99 $329.99
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  37. 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
    $199.99 $299.99
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  38. 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
    $199.99 $299.99
    Add to List View
  39. Men's 6-Inch Premium Waterproof Boot Men's 6-Inch Premium Waterproof Boot
    Men's 6-Inch Premium Waterproof Boot
    $199.99 $329.99
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  40. 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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  41. Men's Earthkeeper® Original Leather 6-Inch Boot Men's Earthkeeper® Original Leather 6-Inch Boot
    Men's Earthkeeper® Original Leather 6-Inch Boot
    $219.99 $319.99
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  42. Men's Mt. Maddsen Waterproof Low Hiker Boot Men's Mt. Maddsen Waterproof Low Hiker Boot
    Men's Mt. Maddsen Waterproof Low Hiker Boot
    $219.99
    Add to List View
  43. 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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  44. 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
    Add to List View
  45. 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
    Add to List View
  46. 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
  47. 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
  48. 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
  49. 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
  50. Men’s Heritage 6-Inch Lace-Up Boot Men’s Heritage 6-Inch Lace-Up Boot
    Men’s Heritage 6-Inch Lace-Up Boot
    $199.99 $329.99
    Add to List View
  51. Men’s Heritage 6-Inch Lace-Up Boot Men’s Heritage 6-Inch Lace-Up Boot
    Men’s Heritage 6-Inch Lace-Up Boot
    $199.99 $329.99
    Add to List View
  52. Men's Winsor Trail Mesh Sneaker Men's Winsor Trail Mesh Sneaker
    Men's Winsor Trail Mesh Sneaker
    $229.99
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  53. Men's Winsor Trail Mesh Sneaker Men's Winsor Trail Mesh Sneaker
    Men's Winsor Trail Mesh Sneaker
    $229.99
    Add to List View
  54. 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
  55. PRO Icon Waterproof Work Boot PRO Icon Waterproof Work Boot
    PRO Icon Waterproof Work Boot
    $249.99 $329.99
    Add to List View
  56. PRO Icon Waterproof Work Boot PRO Icon Waterproof Work Boot
    PRO Icon Waterproof Work Boot
    $249.99 $329.99
    Add to List View
  57. 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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  58. Men's Maple Grove Chukka Men's Maple Grove Chukka
    Men's Maple Grove Chukka
    $259.99
    Add to List View
  59. Men's Maple Grove Chukka Men's Maple Grove Chukka
    Men's Maple Grove Chukka
    $259.99
    Add to List View
  60. Men's Atwells Ave Waterproof Boot Men's Atwells Ave Waterproof Boot
    Men's Atwells Ave Waterproof Boot
    $269.99
    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.