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Footwear

  1. 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
  2. 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
  3. 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
  4. 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
  5. Men's Attleboro 6-Inch Boot
Men's Attleboro 6-Inch Boot
    Men's Attleboro 6-Inch Boot
    $199.99 $299.99
  6. Men's Arbor Road Waterproof Chukka Men's Arbor Road Waterproof Chukka
    Men's Arbor Road Waterproof Chukka
    $199.99 $299.99
  7. Men's Arbor Road Waterproof Chukka Men's Arbor Road Waterproof Chukka
    Men's Arbor Road Waterproof Chukka
    $199.99 $299.99
  8. Men's Winsor Park Chukka Men's Winsor Park Chukka
    Men's Winsor Park Chukka
    $179.99 $259.99
  9. Men's Winsor Park Chukka Men's Winsor Park Chukka
    Men's Winsor Park Chukka
    $179.99 $259.99
  10. 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
  11. 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
  12. 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
  13. Men's Pro Radius Work Sneaker Men's Pro Radius Work Sneaker
    Men's Pro Radius Work Sneaker
    $129.99 $239.99
  14. 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
  15. 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
  16. 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
  17. 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
  18. 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
  19. Men's Original 6-Inch Boot Men's Original 6-Inch Boot
    Men's Original 6-Inch Boot
    $209.99 $319.99
  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
  21. 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
  22. Men's Atwells Ave Waterproof Boot Men's Atwells Ave Waterproof Boot
    Men's Atwells Ave Waterproof Boot
    $129.99 $269.99
  23. Men's Original 6-Inch Boot Men's Original 6-Inch Boot
    Men's Original 6-Inch Boot
    $129.99 $319.99
  24. 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
  25. 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
  26. Men's Westmore Moc-Toe Chukka Men's Westmore Moc-Toe Chukka
    Men's Westmore Moc-Toe Chukka
    $99.99 $269.99
  27. 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
  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
    $139.99 $349.99
  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
  30. Men's Pro Radius Work Sneaker Men's Pro Radius Work Sneaker
    Men's Pro Radius Work Sneaker
    $129.99 $239.99
  31. 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
  32. 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
  33. 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
  34. Men's Waterproof Field Boot Men's Waterproof Field Boot
    Men's Waterproof Field Boot
    $179.99 $259.99
  35. 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
  36. Men's Waterproof Field Boot Men's Waterproof Field Boot
    Men's Waterproof Field Boot
    $179.99 $259.99
  37. Men's Westmore Chukka Men's Westmore Chukka
    Men's Westmore Chukka
    $179.99 $269.99
  38. 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
  39. Men's Classic Boat Shoe Men's Classic Boat Shoe
    Men's Classic Boat Shoe
    $119.99 $199.99
  40. Redwood Falls Waterproof Redwood Falls Waterproof
    Redwood Falls Waterproof
    $199.99 $299.99
  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
  42. Men's Maple Grove Chukka Men's Maple Grove Chukka
    Men's Maple Grove Chukka
    $179.99 $259.99
  43. Men's Atwells Ave Waterproof Boots Men's Atwells Ave Waterproof Boots
    Men's Atwells Ave Waterproof Boots
    $129.99 $269.99
  44. Men's Newmarket II Boot Men's Newmarket II Boot
    Men's Newmarket II Boot
    $159.99 $329.99
  45. 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
  46. Men's Premium Chukka Men's Premium Chukka
    Men's Premium Chukka
    $139.99 $329.99
  47. Men's Atwell Ave Chelsea Boot Men's Atwell Ave Chelsea Boot
    Men's Atwell Ave Chelsea Boot
    $99.99 $259.99
  48. 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
  49. Men's Newmarket II Boot Men's Newmarket II Boot
    Men's Newmarket II Boot
    $159.99 $329.99
  50. 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
  51. 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
  52. 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
  53. Men's Pro Radius Alloy Safety-Toe Work Boots Men's Pro Radius Alloy Safety-Toe Work Boots
    Men's Pro Radius Alloy Safety-Toe Work Boots
    $99.99 $249.99
  54. Men's Westmore Chukka Men's Westmore Chukka
    Men's Westmore Chukka
    $179.99 $269.99
  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
    $99.99 $249.99
  56. TREE VAULT 6 INCH BOOT WP
    TREE VAULT 6 INCH BOOT WP
    $95.99 $299.99
  57. Men's Classic Waterproof Chukka Men's Classic Waterproof Chukka
    Men's Classic Waterproof Chukka
    $94.99 $279.99
  58. EZ LOUNGE SLIP-ON
    EZ LOUNGE SLIP-ON
    $39.99 $179.99
  59. Men's Killington Trekker Low Men's Killington Trekker Low
    Men's Killington Trekker Low
    $89.99 $219.99
  60. SENECA BAY SNEAKER BOOT
    SENECA BAY SNEAKER BOOT
    $59.99 $199.99
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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.