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  1. Richmond Ridge 6-Inch Boot
    View Richmond Ridge 6-Inch Boot
    $360.00
  2. Richmond Ridge 6-Inch Boot
    View Richmond Ridge 6-Inch Boot
    $360.00
  3. Richmond Ridge 6-Inch Boot
    View Richmond Ridge 6-Inch Boot
    $360.00
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    View Men's 6-Inch Premium Waterproof Boots
    Rating:
    100%
    $360.00
  5. Image
    View Men's 6-Inch Premium Waterproof Boots
    Rating:
    100%
    $360.00
  6. Image
    View Men's 6-Inch Premium Waterproof Boots
    Rating:
    100%
    $360.00
  7. Image
    View Men's 6-Inch Premium Boots
    Rating:
    100%
    $360.00
  8. Image
    View Men's Earthkeepers Original 6-Inch Boots
    Rating:
    100%
    $350.00
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    View Men's Earthkeeper's Original 6-Inch Boot
    $350.00
  10. Image
    View Men's 6-Inch Waterproof Rebotl™ Fabric Boot
    Rating:
    100%
    $360.00
  11. Image
    View Men's 6-Inch Waterproof Rebotl™ Fabric Boot
    Rating:
    100%
    $360.00
  12. Image
    View Men's 6-Inch Waterproof Rebotl™ Fabric Boot
    Rating:
    100%
    $360.00
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    View Men's Brooklyn Side Zip Boot
    Rating:
    100%
    $330.00
  14. Image
    View Men's Brooklyn Side Zip Boot
    Rating:
    100%
    $330.00
  15. Image
    View Men's Brooklyn 6-Inch Boot
    Rating:
    100%
    $300.00
  16. Image
    View Men's Brooklyn 6-Inch Boot
    Rating:
    100%
    $300.00
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    View Men's ICON 6-Inch Premium Puffer Boot
    $360.00
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    View Men's ICON 6-Inch Premium Puffer Boot
    $360.00
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    View Men's Jackson's Landing Waterproof Chukka
    Rating:
    100%
    $300.00
  20. Image
    View Men's Jackson's Landing Waterproof Chukka
    $300.00
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    View Men's Squall Canyon Waterproof Chukka Boots
    $320.00
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    View Men's Squall Canyon Waterproof Chukka Boots
    $320.00
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    View Men's Garrison Trail Waterproof Mid Hiker
    $300.00
  24. Image
    View Men's Garrison Trail Waterproof Mid Hiker
    $300.00
  25. Image
    View Mens Cityroam Chukka
    $260.00
  26. Mens Cityroam Chukka
    View Mens Cityroam Chukka
    $260.00
  27. Image
    View Men's Davis Square Chukka
    Rating:
    100%
    $200.00
  28. Image
    View Men's Davis Square Chukka
    Rating:
    100%
    $200.00
  29. Image
    View Men's Yorkdale Chukka
    Rating:
    100%
    $260.00
  30. Image
    View Men's Yorkdale Chukka
    Rating:
    100%
    $260.00
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    View Men's Cityroam Chukka
    $260.00
  32. Image
    View Men's Chocorua Trail 2.0 GoreTex Hiking Boots
    Rating:
    100%
    $350.00
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    View Men's Field Trekker Hiker Low
    $240.00
  34. Image
    View Men's Field Trekker Hiker Low
    $240.00
  35. Image
    View Men's ICON Waterproof Chukka Boots
    $320.00
  36. Image
    View Mens Earthkeepers Original Chukka
    $320.00
  37. Image
    View Mens Earthkeepers Original Chukka
    $320.00
  38. Image
    View Men's Cross Mark Chukka Boot
    $320.00
  39. Image
    clearance
    View Men's Adventure 2.0 Modern Chukka
    Special Price $140.00 Regular Price $280.00
  40. Image
    clearance
    View Men's Bradstreet Chukka Boots
    Special Price $180.00 Regular Price $260.00

40 Items

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Men’s boots

From rugged hiking boots, to stylish urban chukkas, to the original 6-inch boot that started it all. Discover the full Timberland collection of men’s boots, matching authentic style with skilled craftsmanship and premium quality materials. Each pair of Timberland boots are expertly crafted and remain true to our signature look, built with anti-fatigue and waterproof technology to withstand whatever conditions the day throws at you. Shop the range of signature styles and find the boots to match your look, whether that be hiking dirt tracks or roaming around the city streets. These are the boots made to take on the modern trail.