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  1. Size EU 47.5 Remove This Item
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  1. Boots
  2. Sneakers
  3. Shoes
  4. Hiking Boots & Shoes
  5. Boat Shoes & Sandals
  6. Chukka
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  1. Men
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Size US Mens
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Items 1-60 of 101

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  1. Mens 6-Inch Premium Waterproof Boot Wheat Nubuck 11 Men's 6-Inch Premium Waterproof Boot
    Men's 6-Inch Premium Waterproof Boot
    $329.99
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  2. 6 IN PREMIUM FTB BLACK NUBUCK Black Nubuck 11 Men's 6-Inch Premium Waterproof Boot
    Men's 6-Inch Premium Waterproof Boot
    $329.99
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  3. 6 IN PREMIUM BT DK CHOC NUBUCK Dark Chocolate Nubuck 11 Men's 6-Inch Premium Waterproof Boot
    Men's 6-Inch Premium Waterproof Boot
    $329.99
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  4. Mens Earthkeeper Original Leather 6-Inch Boot Red Brown Burnished 11 Men's Earthkeeper® Original Leather 6-Inch Boot
    Men's Earthkeeper® Original Leather 6-Inch Boot
    $319.99
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  5. 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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  6. 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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  7. Men's Icon Waterproof Chukka Boot Men's Icon Waterproof Chukka Boot
    Men's Icon Waterproof Chukka Boot
    $299.99
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  8. 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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  9. 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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  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
    $219.99 $329.99
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  11. Men’s Heritage 6-Inch Lace-Up Boot Men’s Heritage 6-Inch Lace-Up Boot
    Men’s Heritage 6-Inch Lace-Up Boot
    $219.99 $329.99
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  12. Men’s Heritage 6-Inch Lace-Up Boot Men’s Heritage 6-Inch Lace-Up Boot
    Men’s Heritage 6-Inch Lace-Up Boot
    $219.99 $329.99
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  13. Men's Classic 6-Inch Waterproof Boot Men's Classic 6-Inch Waterproof Boot
    Men's Classic 6-Inch Waterproof Boot
    $189.99 $279.99
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  14. Men's Classic 6-Inch Waterproof Boot Men's Classic 6-Inch Waterproof Boot
    Men's Classic 6-Inch Waterproof Boot
    $189.99 $279.99
    Add to List View
  15. PRO Icon Waterproof Work Boot PRO Icon Waterproof Work Boot
    PRO Icon Waterproof Work Boot
    $229.99 $329.99
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  16. PRO Icon Waterproof Work Boot PRO Icon Waterproof Work Boot
    PRO Icon Waterproof Work Boot
    $229.99 $329.99
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  17. 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
    $169.99 $249.99
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  18. 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
    $169.99 $249.99
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  19. 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
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  20. 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
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  21. Men's Crestfield Waterproof Sneaker Men's Crestfield Waterproof Sneaker
    Men's Crestfield Waterproof Sneaker
    $159.99 $269.99
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  22. Men's Crestfield Waterproof Sneaker Men's Crestfield Waterproof Sneaker
    Men's Crestfield Waterproof Sneaker
    $159.99 $269.99
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  23. Men's Treeline Mountain Runner Shoe Men's Treeline Mountain Runner Shoe
    Men's Treeline Mountain Runner Shoe
    $99.99 $169.99
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  24. Men's Seneca Bay Sneaker Men's Seneca Bay Sneaker
    Men's Seneca Bay Sneaker
    $149.99 $219.99
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  25. Men's Seneca Bay Sneaker Men's Seneca Bay Sneaker
    Men's Seneca Bay Sneaker
    $149.99 $219.99
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  26. Mens Authentics 3-eye Classic Lug Shoe Medium Brown/Full Grain 11 Men's Authentics 3-Eye Classic Boat Shoe
    Men's Authentics 3-Eye Classic Boat Shoe
    $249.99
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  27. Mens 2-eye Boat Shoe Root Beer Smooth 11 Men's 2-Eye Boat Shoe
    Men's 2-Eye Boat Shoe
    $199.99
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  28. Men's Authentics 3 Eye Classic Men's Authentics 3 Eye Classic
    Men's Authentics 3 Eye Classic
    $159.99 $249.99
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  29. 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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  30. 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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  31. 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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  32. 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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  33. 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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  34. 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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  35. Men's 6-Inch Alburn Boot Men's 6-Inch Alburn Boot
    Men's 6-Inch Alburn Boot
    $189.99 $279.99
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  36. Men's 6-Inch Alburn Boot Men's 6-Inch Alburn Boot
    Men's 6-Inch Alburn Boot
    $189.99 $279.99
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  37. Men's Waterproof Field Boot Men's Waterproof Field Boot
    Men's Waterproof Field Boot
    $179.99 $259.99
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  38. 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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  39. 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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  40. 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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  41. 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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  42. 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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  43. Men's Maple Grove Chukka Men's Maple Grove Chukka
    Men's Maple Grove Chukka
    $179.99 $259.99
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  44. Men's Maple Grove Chukka Men's Maple Grove Chukka
    Men's Maple Grove Chukka
    $179.99 $259.99
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  45. Men's Redwood Falls Waterproof Chukka Boot Men's Redwood Falls Waterproof Chukka Boot
    Men's Redwood Falls Waterproof Chukka Boot
    $189.99 $279.99
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  46. 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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  47. 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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  48. Men's Davis Square Chukka Men's Davis Square Chukka
    Men's Davis Square Chukka
    $149.99 $219.99
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  49. Men's Winsor Park Chukka Men's Winsor Park Chukka
    Men's Winsor Park Chukka
    $179.99 $259.99
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  50. Men's Winsor Park Chukka Men's Winsor Park Chukka
    Men's Winsor Park Chukka
    $179.99 $259.99
    Add to List View
  51. Men's Killington Low Lace-Up Sneaker Men's Killington Low Lace-Up Sneaker
    Men's Killington Low Lace-Up Sneaker
    $124.99 $179.99
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  52. Men's Killington Low Lace-Up Sneaker Men's Killington Low Lace-Up Sneaker
    Men's Killington Low Lace-Up Sneaker
    $124.99 $179.99
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  53. Men's Seneca Bay Low Lace-Up Sneaker Men's Seneca Bay Low Lace-Up Sneaker
    Men's Seneca Bay Low Lace-Up Sneaker
    $109.99 $169.99
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  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. Men's Maple Grove Low Lace-Up Sneaker Men's Maple Grove Low Lace-Up Sneaker
    Men's Maple Grove Low Lace-Up Sneaker
    $159.99 $239.99
    Add to List View
  56. Men's Maple Grove Low Lace-Up Sneaker Men's Maple Grove Low Lace-Up Sneaker
    Men's Maple Grove Low Lace-Up Sneaker
    $159.99 $239.99
    Add to List View
  57. Men's Winsor Park Trainer Men's Winsor Park Trainer
    Men's Winsor Park Trainer
    $159.99 $229.99
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  58. Men's Winsor Park Trainer Men's Winsor Park Trainer
    Men's Winsor Park Trainer
    $159.99 $229.99
    Add to List View
  59. Men's Basic Oxford Men's Basic Oxford
    Men's Basic Oxford
    $159.99 $239.99
    Add to List View
  60. Men's Cedar Bay Boat Shoe Men's Cedar Bay Boat Shoe
    Men's Cedar Bay Boat Shoe
    $149.99 $229.99
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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.