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Items 1-60 of 100

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  1. 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
    $319.99
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  2. 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
    $319.99
    Add to List View
  3. 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
    $319.99
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  4. 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
    $299.99
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  5. 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
    $299.99
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  6. Men's Classic 6-Inch Waterproof Boots Men's Classic 6-Inch Waterproof Boots
    Men's Classic 6-Inch Waterproof Boots
    $279.99
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  7. Men's Classic 6-Inch Waterproof Boots Men's Classic 6-Inch Waterproof Boots
    Men's Classic 6-Inch Waterproof Boots
    $279.99
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  8. Men’s Heritage 6-Inch Lace-Up Boot Men’s Heritage 6-Inch Lace-Up Boot
    Men’s Heritage 6-Inch Lace-Up Boot
    $329.99
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  9. Men’s Heritage 6-Inch Lace-Up Boot Men’s Heritage 6-Inch Lace-Up Boot
    Men’s Heritage 6-Inch Lace-Up Boot
    $329.99
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  10. Men’s Heritage 6-Inch Lace-Up Boot Men’s Heritage 6-Inch Lace-Up Boot
    Men’s Heritage 6-Inch Lace-Up Boot
    $329.99
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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
    $279.99
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  12. Men's Classic 6-Inch Waterproof Boot Men's Classic 6-Inch Waterproof Boot
    Men's Classic 6-Inch Waterproof Boot
    $279.99
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  13. Men's Attleboro 6-Inch Boot Men's Attleboro 6-Inch Boot
    Men's Attleboro 6-Inch Boot
    $299.99
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  14. 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
    $329.99
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  15. Men's Maple Grove Chukka Men's Maple Grove Chukka
    Men's Maple Grove Chukka
    $259.99
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  16. Men's Maple Grove Chukka Men's Maple Grove Chukka
    Men's Maple Grove Chukka
    $259.99
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  17. Men's Redwood Falls Waterproof Chukka Boot Men's Redwood Falls Waterproof Chukka Boot
    Men's Redwood Falls Waterproof Chukka Boot
    $279.99
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  18. PRO Icon Waterproof Work Boot PRO Icon Waterproof Work Boot
    PRO Icon Waterproof Work Boot
    $329.99
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  19. PRO Icon Waterproof Work Boot PRO Icon Waterproof Work Boot
    PRO Icon Waterproof Work Boot
    $329.99
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  20. Men's Pro Helix HD 6-Inch Composite Toe Work Boot Men's Pro Helix HD 6-Inch Composite Toe Work Boot
    Men's Pro Helix HD 6-Inch Composite Toe Work Boot
    $249.99
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  21. Men's Pro Helix HD 6-Inch Composite Toe Work Boot Men's Pro Helix HD 6-Inch Composite Toe Work Boot
    Men's Pro Helix HD 6-Inch Composite Toe Work Boot
    $249.99
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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
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  23. Men's Killington Low Lace-Up Sneaker Men's Killington Low Lace-Up Sneaker
    Men's Killington Low Lace-Up Sneaker
    $179.99
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  24. Men's Davis Square Chukka Men's Davis Square Chukka
    Men's Davis Square Chukka
    $219.99
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  25. Men's Winsor Park Trainer Men's Winsor Park Trainer
    Men's Winsor Park Trainer
    $229.99
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  26. Men's Seneca Bay Sneaker Men's Seneca Bay Sneaker
    Men's Seneca Bay Sneaker
    $219.99
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  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
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  28. Men's Seneca Bay Sneaker Men's Seneca Bay Sneaker
    Men's Seneca Bay Sneaker
    $219.99
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  29. Men's Crestfield Waterproof Sneaker Men's Crestfield Waterproof Sneaker
    Men's Crestfield Waterproof Sneaker
    $269.99
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  30. Men's Crestfield Waterproof Sneaker Men's Crestfield Waterproof Sneaker
    Men's Crestfield Waterproof Sneaker
    $269.99
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  31. Men's Authentics 3 Eye Classic Men's Authentics 3 Eye Classic
    Men's Authentics 3 Eye Classic
    $249.99
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  32. Men's Cedar Bay Boat Shoe Men's Cedar Bay Boat Shoe
    Men's Cedar Bay Boat Shoe
    $229.99
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  33. Men's Cedar Bay Boat Shoe Men's Cedar Bay Boat Shoe
    Men's Cedar Bay Boat Shoe
    $229.99
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  34. Men's Waterproof Field Boot Men's Waterproof Field Boot
    Men's Waterproof Field Boot
    $259.99
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  35. Men's Basic Oxford Men's Basic Oxford
    Men's Basic Oxford
    $239.99
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  36. Men's Winsor Park Trainer Men's Winsor Park Trainer
    Men's Winsor Park Trainer
    $229.99
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  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
    $239.99
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  38. 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
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  39. Men's Redwood Falls Waterproof Chukka Boot Men's Redwood Falls Waterproof Chukka Boot
    Men's Redwood Falls Waterproof Chukka Boot
    $279.99
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  40. Men's Euro Hiker Boot Men's Euro Hiker Boot
    Men's Euro Hiker Boot
    $269.99
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  41. 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
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  42. 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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  43. 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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  44. 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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  45. 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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  46. 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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  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
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  48. 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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  49. 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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  50. Men's Winsor Park Chukka Men's Winsor Park Chukka
    Men's Winsor Park Chukka
    $179.99 $259.99
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  51. Men's Winsor Park Chukka Men's Winsor Park Chukka
    Men's Winsor Park Chukka
    $179.99 $259.99
    Add to List View
  52. 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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  53. 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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  54. 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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  55. Redwood Falls Waterproof Redwood Falls Waterproof
    Redwood Falls Waterproof
    $199.99 $299.99
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  56. Men's Maple Grove Chukka Men's Maple Grove Chukka
    Men's Maple Grove Chukka
    $179.99 $259.99
    Add to List View
  57. 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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  58. 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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  59. 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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  60. 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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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.