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Chukka Boots

25 Items

per page
  1. Image
    View Men's Flyroam Chill Chukka
    $280.00
  2. Image
    View Men's Davis Square Fabric and Leather Chukka
    $220.00
  3. Image
    View Men's Kendrick Chukka
    $300.00
  4. Image
    View Men's Altimeter Fabric and Leather Chukka
    $240.00
  5. Image
    View Men's Cityroam Cupsole Chukka
    $260.00
  6. Image
    View Men's Flyroam Leather Hiker
    $280.00
  7. Image
    View Men's City's Edge Chukka with GoreTex
    $360.00
  8. Image
    View Men's Altimeter Fabric and Leather Chukka
    $240.00
    CLEARANCE
  9. Image
    View Men's Cityroam Cupsole Alpine Chukka
    $260.00
  10. Image
    View Men's Flyroam Leather Hiker
    $280.00
  11. Image
    View Men's Cross Mark Plain Toe Chukka
    $280.00
  12. Image
    View Men's Flyroam Go Leather Chukka
    $300.00
  13. Image
    View Men's Kendrick Chukka
    $300.00
  14. Image
    View Men's Altimeter Fabric and Leather Chukka
    $240.00
  15. Image
    View Men's Cityroam Cupsole Chukka
    $260.00
  16. Image
    View Men's Flyroam Chill Chukka
    $280.00
  17. Image
    View Men's City's Edge Chukka with GoreTex
    $360.00
  18. Image
    View Men's Adventure 2.0 Cupsole Chukka
    $300.00
  19. Image
    View Men's Cityroam Cupsole Alpine Chukka
    $260.00
  20. Image
    View Men's Flyroam Leather Hiker
    $280.00
  21. Image
    View Men's Cross Mark Plain Toe Chukka
    $280.00
  22. Image
    View Men's Bradstreet Chukka
    $280.00
  23. Image
    View Men's ICON Waterproof Chukka
    $320.00
  24. Image
    View Men's Altimeter Fabric and Leather Chukka
    $240.00
  25. Image
    View Men's Cityroam Cupsole Chukka
    $260.00

25 Items

per page

Men’s Chukka Boots

For a rugged take on modern street style, see the Timberland collection of men’s chukka boots. Designed for effortless off-duty style, our men’s chukka boots provide a relaxed look and comfortable fit, with built in padded ankle technology to support your feet as you move through the day. If you’re looking for a polished dress-shoe style that doesn’t compromise on comfort, discover our classic Kendrick Chukka. Tackle whatever adventure the day throws at you with our men’s chukkas. Built for comfort and a lifetime of wear. Set out on your next urban adventure with a pair of Timberland chukkas.