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Category
  1. Boots
  2. Sneakers
  3. Shoes
  4. Dress Shoes
  5. Hiking Boots & Shoes
  6. Boat Shoes & Sandals
  7. Chukka
Gender
  1. Men
  2. Women
Material
  1. Leather
  2. Mesh
  3. Nylon
  4. Suede
  5. Nubuck
Size
3/4
Size US Mens
6
7
8
9
10
11
12
13
14
15
Size US Womens
9
10
11
Size EU
39
40
41.5
42
43
44
45
46
47.5
49
50
Size UK
5.5
6.5
7
7.5
8
8.5
9
9.5
10.5
11.5
12.5
13.5
14.5
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Items 61-120 of 131

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  1. Men's Attleboro Mid Lace-Up Chukka Men's Attleboro Mid Lace-Up Chukka
    Men's Attleboro Mid Lace-Up Chukka
    $299.99
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  2. 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
  3. Men's Winsor Park Chukka Men's Winsor Park Chukka
    Men's Winsor Park Chukka
    $179.99 $259.99
    Add to List View
  4. Men's Winsor Park Chukka Men's Winsor Park Chukka
    Men's Winsor Park Chukka
    $179.99 $259.99
    Add to List View
  5. 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
  6. 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
  7. 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
    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 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
    Add to List View
  11. Men's Pro Reaxion Composite Toe Work Sneaker Men's Pro Reaxion Composite Toe Work Sneaker
    Men's Pro Reaxion Composite Toe Work Sneaker
    $79.99
    Add to List View
  12. 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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  13. Men's Pro Radius Work Sneaker Men's Pro Radius Work Sneaker
    Men's Pro Radius Work Sneaker
    $129.99 $239.99
    Add to List View
  14. 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
  15. 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
    Add to List View
  16. 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
  17. 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
  18. Men's Original 6-Inch Boot Men's Original 6-Inch Boot
    Men's Original 6-Inch Boot
    $209.99 $319.99
    Add to List View
  19. 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
  20. 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
  21. 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
  22. 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
  23. 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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  24. 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
  25. 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
  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
    Add to List View
  27. 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
  28. Men's Atwells Ave Waterproof Boot Men's Atwells Ave Waterproof Boot
    Men's Atwells Ave Waterproof Boot
    $269.99
    Add to List View
  29. Men's Newmarket II Boot Men's Newmarket II Boot
    Men's Newmarket II Boot
    $159.99 $329.99
    Add to List View
  30. Men's Westmore Chukka Men's Westmore Chukka
    Men's Westmore Chukka
    $179.99 $269.99
    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
    Add to List View
  33. Men's GreenStride™ Atwells Ave Waterproof Chukka Boot Men's GreenStride™ Atwells Ave Waterproof Chukka Boot
    Men's GreenStride™ Atwells Ave Waterproof Chukka Boot
    $279.99
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  34. Men's Westmore Chukka Men's Westmore Chukka
    Men's Westmore Chukka
    $179.99 $269.99
    Add to List View
  35. Men's Treeline Mountain Runner Shoe Men's Treeline Mountain Runner Shoe
    Men's Treeline Mountain Runner Shoe
    $169.99
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  36. Men's Treeline Mountain Runner Shoe Men's Treeline Mountain Runner Shoe
    Men's Treeline Mountain Runner Shoe
    $169.99
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  37. 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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  38. Men's Newmarket II Boot Men's Newmarket II Boot
    Men's Newmarket II Boot
    $159.99 $329.99
    Add to List View
  39. 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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  40. 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
  41. 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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  42. Men's Redwood Falls Waterproof Boot Men's Redwood Falls Waterproof Boot
    Men's Redwood Falls Waterproof Boot
    $299.99
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  43. 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
  44. 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
  45. Men's Premium Chukka Men's Premium Chukka
    Men's Premium Chukka
    $139.99 $329.99
    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
    $99.99 $249.99
    Add to List View
  47. 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
  48. Men's Killington Trekker Low Men's Killington Trekker Low
    Men's Killington Trekker Low
    $89.99 $219.99
    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
    $139.99 $249.99
    Add to List View
  50. Men's Classic Waterproof Chukka Men's Classic Waterproof Chukka
    Men's Classic Waterproof Chukka
    $94.99 $279.99
    Add to List View
  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 Classic 6-Inch Waterproof Boot Men's Classic 6-Inch Waterproof Boot
    Men's Classic 6-Inch Waterproof Boot
    $99.99 $279.99
    Add to List View
  53. 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
  54. 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
    Add to List View
  55. 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
  56. 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
  57. Men's Classic Boat Shoe Men's Classic Boat Shoe
    Men's Classic Boat Shoe
    $119.99 $199.99
    Add to List View
  58. 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
  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
    $119.99 $229.99
    Add to List View
  60. Men's Newmarket II Moc Toe Chukka
    Men's Newmarket II Moc Toe Chukka
    $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.