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24 Items

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  1. Image
    View Men's 6-Inch Premium Waterproof Boots
    Rating:
    100%
    $360.00
  2. Image
    View Men's Kendrick Waterproof Chukka Boots
    $350.00
  3. Image
    View Men's Kendrick Waterproof Chukka Boots
    $350.00
  4. Image
    View Men's Davis Square Leather and Fabric Chukka Boots
    $220.00
  5. Image
    View Men's Davis Square Leather and Fabric Chukka Boots
    $220.00
  6. Image
    View Men's Bradstreet Chukka Boots
    $280.00
  7. Image
    View Men's 6-Inch Premium Waterproof Boots
    Rating:
    100%
    $360.00
  8. Image
    View Men's 6-Inch Premium Waterproof Boots
    $360.00
  9. Image
    View Men's White Ledge Waterproof Mid Boots
    $300.00
  10. Image
    View Men's White Ledge Waterproof Mid Boots
    $300.00
  11. Image
    View Men's Chocorua Trail 2.0 GoreTex Hiking Boots
    Rating:
    100%
    $350.00
  12. Image
    View Men's ICON Waterproof Chukka Boots
    $320.00
  13. Image
    View Men's Yorkdale Chukka Boots
    $300.00
  14. Image badge image
    View Men's Bradstreet Chukka Boots
    $260.00
  15. Image
    View Men's Yorkdale Chukka Boots
    $300.00
  16. Image
    clearance
    View Men's 6-Inch Premium Waterproof Boots
    $320.00
  17. Image
    clearance
    View Men's 6-Inch Premium Waterproof Boots
    $288.00
  18. Image
    clearance
    View Men's Adventure 2.0 Modern Chukka Boots
    $168.00
  19. Image
    clearance
    View Men's Flyroam Chill Chukka Boots
    Rating:
    100%
    $168.00
  20. Image
    clearance
    View Men's 6-Inch Premium Waterproof Boots
    $288.00
  21. Image
    clearance
    View Men's 6-Inch Premium Waterproof Boots
    $288.00
  22. Image
    clearance
    View Men's Cityroam Chukka Boots
    $182.00
  23. Image
    clearance
    View Men's Cityroam Chukka Boots
    $182.00
  24. Image
    clearance
    View Men's ICON 6-Inch Premium Chelsea Boots
    $231.00

24 Items

per page

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.