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  1. Size UK 12.5 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 61-116 of 116

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  1. 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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  2. 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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  3. 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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  4. 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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  5. Men's Mt. Maddsen Waterproof Low Hiker Boot Men's Mt. Maddsen Waterproof Low Hiker Boot
    Men's Mt. Maddsen Waterproof Low Hiker Boot
    $149.99 $219.99
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  6. 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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  7. MYLO BAY LACE UP SHOE
    MYLO BAY LACE UP SHOE
    $149.95
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  8. 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
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  9. 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
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  10. 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
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  11. 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
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  12. 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
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  13. 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
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  14. Men's Original 6-Inch Boot Men's Original 6-Inch Boot
    Men's Original 6-Inch Boot
    $209.99 $319.99
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  15. 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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  16. Men's Atwells Ave Waterproof Boot Men's Atwells Ave Waterproof Boot
    Men's Atwells Ave Waterproof Boot
    $129.99 $269.99
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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
    $189.99 $279.99
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  18. Men's Treeline Mountain Runner Shoe Men's Treeline Mountain Runner Shoe
    Men's Treeline Mountain Runner Shoe
    $169.99
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  19. 6IN PREMIUM BOOT
    6IN PREMIUM BOOT
    $239.99 $349.99
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  20. 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
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  21. Men's Treeline Mountain Runner Shoe Men's Treeline Mountain Runner Shoe
    Men's Treeline Mountain Runner Shoe
    $169.99
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  22. 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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  23. AUTHENTICS 3 EYE CLASSIC BOAT SHOE
    AUTHENTICS 3 EYE CLASSIC BOAT SHOE
    $259.99
    Add to List View
  24. 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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  25. 6IN PREMIUM BOOT
    6IN PREMIUM BOOT
    $239.99 $349.99
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  26. PREMIUM 6 INCH LACE UP BOOT
    PREMIUM 6 INCH LACE UP BOOT
    $239.99 $349.99
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  27. 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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  28. 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
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  29. BALLAST 6 IN STEEL TOE WORK BOOT
    BALLAST 6 IN STEEL TOE WORK BOOT
    $119.99 $259.99
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  30. 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
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  31. Men's Cedar Bay Boat Shoe Men's Cedar Bay Boat Shoe
    Men's Cedar Bay Boat Shoe
    $229.99
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  32. 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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  33. 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
  34. 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
  35. Men's Waterproof Field Boot Men's Waterproof Field Boot
    Men's Waterproof Field Boot
    $179.99 $259.99
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  36. Men's Euro Hiker Boot Men's Euro Hiker Boot
    Men's Euro Hiker Boot
    $179.99 $269.99
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  37. 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
  38. Men's Waterproof Field Boot Men's Waterproof Field Boot
    Men's Waterproof Field Boot
    $179.99 $259.99
    Add to List View
  39. Men's Attleboro Mid Lace-Up Chukka Men's Attleboro Mid Lace-Up Chukka
    Men's Attleboro Mid Lace-Up Chukka
    $199.99 $299.99
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  40. Men's Atwells Ave Waterproof Boot Men's Atwells Ave Waterproof Boot
    Men's Atwells Ave Waterproof Boot
    $269.99
    Add to List View
  41. Men's Classic Boat Shoe Men's Classic Boat Shoe
    Men's Classic Boat Shoe
    $119.99 $199.99
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  42. Men's Maple Grove Chukka Men's Maple Grove Chukka
    Men's Maple Grove Chukka
    $179.99 $259.99
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  43. Men's Newmarket II Boot Men's Newmarket II Boot
    Men's Newmarket II Boot
    $159.99 $329.99
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  44. Men’s Garrison Trail WP Mid Hiker Boots Men’s Garrison Trail WP Mid Hiker Boots
    Men’s Garrison Trail WP Mid Hiker Boots
    $129.99 $259.99
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  45. Men’s Garrison Trail Low AC Hiking Sneakers Men’s Garrison Trail Low AC Hiking Sneakers
    Men’s Garrison Trail Low AC Hiking Sneakers
    $109.99 $199.99
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  46. Men's Redwood Falls Waterproof Boot Men's Redwood Falls Waterproof Boot
    Men's Redwood Falls Waterproof Boot
    $299.99
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  47. 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
  48. Men's Premium Chukka Men's Premium Chukka
    Men's Premium Chukka
    $139.99 $329.99
    Add to List View
  49. Men’s Garrison Trail Hiking Sneakers Men’s Garrison Trail Hiking Sneakers
    Men’s Garrison Trail Hiking Sneakers
    $109.99 $199.99
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  50. 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
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  51. 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
  52. Men's Westmore Chukka Men's Westmore Chukka
    Men's Westmore Chukka
    $179.99 $269.99
    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
    $99.99 $249.99
    Add to List View
  54. 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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  55. Men's Killington Trekker Low Men's Killington Trekker Low
    Men's Killington Trekker Low
    $89.99 $219.99
    Add to List View
  56. Men's Westmore Chukka Men's Westmore Chukka
    Men's Westmore Chukka
    $179.99 $269.99
    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.