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Category
  1. Boots
  2. Sneakers
  3. Shoes
  4. Hiking Boots & Shoes
  5. Boat Shoes & Sandals
  6. Chukka
Gender
  1. Men
  2. Unisex
Size
3/4
Size US Mens
6
7
7.5
8
8.5
9
10
11
12
13
14
15
Size US Womens
7.5
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 61-119 of 125

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  1. Men's Classic Leather Boat Shoe Men's Classic Leather Boat Shoe
    Men's Classic Leather Boat Shoe
    $199.99
    Add to List View
  2. Men's Classic Leather Boat Shoe Men's Classic Leather Boat Shoe
    Men's Classic Leather Boat Shoe
    $199.99
    Add to List View
  3. 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
  4. Men's Classic Leather Boat Shoe Men's Classic Leather Boat Shoe
    Men's Classic Leather Boat Shoe
    $199.99
    Add to List View
  5. 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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  6. 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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  7. 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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  8. 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
  9. 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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  10. 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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  11. Men's Westmore Chukka Men's Westmore Chukka
    Men's Westmore Chukka
    $179.99 $269.99
    Add to List View
  12. 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
  13. Men's Winsor Park Chukka Men's Winsor Park Chukka
    Men's Winsor Park Chukka
    $179.99 $259.99
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  14. Men's Winsor Park Chukka Men's Winsor Park Chukka
    Men's Winsor Park Chukka
    $179.99 $259.99
    Add to List View
  15. Men's Maple Grove Chukka Men's Maple Grove Chukka
    Men's Maple Grove Chukka
    $179.99 $259.99
    Add to List View
  16. Men's Waterproof Field Boot Men's Waterproof Field Boot
    Men's Waterproof Field Boot
    $179.99 $259.99
    Add to List View
  17. 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
  18. 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
  19. 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
  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 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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  22. 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
  23. 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
  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 Westmore Chukka Men's Westmore Chukka
    Men's Westmore Chukka
    $179.99 $269.99
    Add to List View
  26. 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
  27. 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
    Add to List View
  28. 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
  29. 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
  30. Men's Newmarket II Boot Men's Newmarket II Boot
    Men's Newmarket II Boot
    $159.99 $329.99
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  31. Men's Newmarket II Boot Men's Newmarket II Boot
    Men's Newmarket II Boot
    $159.99 $329.99
    Add to List View
  32. Men's Waterproof Field Boot Men's Waterproof Field Boot
    Men's Waterproof Field Boot
    $159.99 $259.99
    Add to List View
  33. Men's Pro Reaxion Composite Toe Mid Sneaker Men's Pro Reaxion Composite Toe Mid Sneaker
    Men's Pro Reaxion Composite Toe Mid Sneaker
    $149.99
    Add to List View
  34. Men's Davis Square Chukka Men's Davis Square Chukka
    Men's Davis Square Chukka
    $149.99 $219.99
    Add to List View
  35. Men's Seneca Bay Sneaker Men's Seneca Bay Sneaker
    Men's Seneca Bay Sneaker
    $149.99 $219.99
    Add to List View
  36. Men's Maple Grove Low Lace-Up Sneaker Men's Maple Grove Low Lace-Up Sneaker
    Men's Maple Grove Low Lace-Up Sneaker
    $149.99 $239.99
    Add to List View
  37. Men's Maple Grove Low Lace-Up Sneaker Men's Maple Grove Low Lace-Up Sneaker
    Men's Maple Grove Low Lace-Up Sneaker
    $149.99 $239.99
    Add to List View
  38. Men's Seneca Bay Sneaker Men's Seneca Bay Sneaker
    Men's Seneca Bay Sneaker
    $149.99 $219.99
    Add to List View
  39. Men's Seaton Bay Cross-Strap Sandal Men's Seaton Bay Cross-Strap Sandal
    Men's Seaton Bay Cross-Strap Sandal
    $149.99
    Add to List View
  40. Men's Seaton Bay Cross-Strap Sandal Men's Seaton Bay Cross-Strap Sandal
    Men's Seaton Bay Cross-Strap Sandal
    $149.99
    Add to List View
  41. 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
  42. Men's Premium Chukka Men's Premium Chukka
    Men's Premium Chukka
    $139.99 $329.99
    Add to List View
  43. 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
  44. Men's Classic 6-Inch Waterproof Boot Men's Classic 6-Inch Waterproof Boot
    Men's Classic 6-Inch Waterproof Boot
    $139.99 $279.99
    Add to List View
  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
    Add to List View
  46. 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
  47. Men's Atwells Ave Waterproof Boots Men's Atwells Ave Waterproof Boots
    Men's Atwells Ave Waterproof Boots
    $129.99 $269.99
    Add to List View
  48. 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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  49. Men's GreenStride™ Atwells Ave Waterproof Chukka Boot Men's GreenStride™ Atwells Ave Waterproof Chukka Boot
    Men's GreenStride™ Atwells Ave Waterproof Chukka Boot
    $129.99 $259.99
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  50. 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
  51. Men's Premium 6-Inch Waterproof Boot Men's Premium 6-Inch Waterproof Boot
    Men's Premium 6-Inch Waterproof Boot
    $129.99 $349.99
    Add to List View
  52. 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
  53. 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
  54. 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
  55. Men's Classic Boat Shoe Men's Classic Boat Shoe
    Men's Classic Boat Shoe
    $119.99 $199.99
    Add to List View
  56. Men’s Garrison Trail WP Mid Hiker Boots Men’s Garrison Trail WP Mid Hiker Boots
    Men’s Garrison Trail WP Mid Hiker Boots
    $99.99 $259.99
    Add to List View
  57. 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
  58. 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
  59. 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
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Explore your favourite Men's Timberland Footwear at discounted prices in our men's sale. Find the popular styles like our Men's Premium 6-Inch Boots or our range of Men's Hiking Boots. For something more versatile that will take you from casual to formal, browse our collection of Men's Boat Shoes. For a full Timberland look from head to toe, make sure to browse our range of Men's Accessories. If you're planning to shop our Black Friday sale, sign up to our mailing list 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 Footwear Sale online today.