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Casual Shoes

Mens
  1. Men's Amherst Leather Slip-On Shoe Men's Amherst Leather Slip-On Shoe
    TIMBERLAND Men's Amherst Leather Slip-On Shoe
    $199.95
  2. Men's Radford 6-Inch Waterproof Boot Men's Radford 6-Inch Waterproof Boot
    TIMBERLAND Men's Radford 6-Inch Waterproof Boot
    $299.95
  3. Men's Radford 6-Inch Roll Top Black Men's Radford 6-Inch Roll Top Black
    TIMBERLAND Men's Radford 6-Inch Roll Top Black
    $299.95
  4. Men's Radford 6-Inch Roll Top Black Men's Radford 6-Inch Roll Top Black
    TIMBERLAND Men's Radford 6-Inch Roll Top Black
    $299.95
  5. Men's Radford 7" Boot Men's Radford 7" Boot
    TIMBERLAND Men's Radford 7" Boot
    From $299.95 $329.95
  6. Men's Radford Leather Chukka Boot Men's Radford Leather Chukka Boot
    TIMBERLAND Men's Radford Leather Chukka Boot
    $239.95
  7. Men's Radford Leather Chukka Boot Men's Radford Leather Chukka Boot
    TIMBERLAND Men's Radford Leather Chukka Boot
    $239.95
  8. Men's Amherst Leather Slip-On Shoe Men's Amherst Leather Slip-On Shoe
    TIMBERLAND Men's Amherst Leather Slip-On Shoe
    $199.95
  9. Men's LTD Boot Men's LTD Boot
    TIMBERLAND Men's LTD Boot
    From $299.95 $349.95
  10. Men's LTD Boot Men's LTD Boot
    TIMBERLAND Men's LTD Boot
    From $299.95 $349.95
  11. Men's Bradstreet Chukka Boot Men's Bradstreet Chukka Boot
    TIMBERLAND Men's Bradstreet Chukka Boot
    $249.95
  12. Men's Bradstreet Chukka Boot Men's Bradstreet Chukka Boot
    TIMBERLAND Men's Bradstreet Chukka Boot
    $249.95
  13. Men's Stormbuck Plain Toe Shoe Men's Stormbuck Plain Toe Shoe
    TIMBERLAND Men's Stormbuck Plain Toe Shoe
    From $149 $179
  14. Men's Stormbuck Plain Toe Shoe Men's Stormbuck Plain Toe Shoe
    TIMBERLAND Men's Stormbuck Plain Toe Shoe
    From $149 $179
  15. Men's Franklin Park Chukka Shoe Men's Franklin Park Chukka Shoe
    TIMBERLAND Men's Franklin Park Chukka Shoe
    $249.95
  16. Men's Radford Leather Chukka Boot Men's Radford Leather Chukka Boot
    TIMBERLAND Men's Radford Leather Chukka Boot
    $279.95
  17. Men's Radford Leather Chukka Boot Men's Radford Leather Chukka Boot
    TIMBERLAND Men's Radford Leather Chukka Boot
    $279.95
  18. Men's Adventure 2.0 Cupsole Chukka
    TIMBERLAND Men's Adventure 2.0 Cupsole Chukka
    $259.95
  19. Men's 6-Inch Premium Waterproof Boot Men's 6-Inch Premium Waterproof Boot
    TIMBERLAND Men's 6-Inch Premium Waterproof Boot
    $299.95
  20. Men's 6-Inch Premium Waterproof Boot Men's 6-Inch Premium Waterproof Boot
    TIMBERLAND Men's 6-Inch Premium Waterproof Boot
    $299.95
  21. Men's 6-Inch Premium Waterproof Boot Men's 6-Inch Premium Waterproof Boot
    TIMBERLAND Men's 6-Inch Premium Waterproof Boot
    $299.95
  22. Men's 6-Inch Premium Boot Men's 6-Inch Premium Boot
    TIMBERLAND Men's 6-Inch Premium Boot
    From $269.95 $279.95
  23. Mens TPU Outsole Roll Top Boots Mens TPU Outsole Roll Top Boots
    TIMBERLAND Mens TPU Outsole Roll Top Boots
    From $129 $299.95
  24. Mens Amherst Chelsea Boots Mens Amherst Chelsea Boots
    TIMBERLAND Mens Amherst Chelsea Boots
    From $149 $239.95
  25. Men's Giri Radford 6-Inch Boot Men's Giri Radford 6-Inch Boot
    TIMBERLAND Men's Giri Radford 6-Inch Boot
    From $149 $229.95
  26. Men's Kendrick Chelsea Men's Kendrick Chelsea
    TIMBERLAND Men's Kendrick Chelsea
    $279.95
  27. Men's Kendrick Chelsea Men's Kendrick Chelsea
    TIMBERLAND Men's Kendrick Chelsea
    $279.95
  28. Men's 6-Inch Vecchio Premium Boot Men's 6-Inch Vecchio Premium Boot
    TIMBERLAND Men's 6-Inch Vecchio Premium Boot
    $299.95
  29. Men's 6-Inch Vecchio Premium Boot Men's 6-Inch Vecchio Premium Boot
    TIMBERLAND Men's 6-Inch Vecchio Premium Boot
    $299.95
  30. Men's 6-Inch Vecchio Premium Boot Men's 6-Inch Vecchio Premium Boot
    TIMBERLAND Men's 6-Inch Vecchio Premium Boot
    $299.95
  31. Men's Icon Chelsea Boot Men's Icon Chelsea Boot
    TIMBERLAND Men's Icon Chelsea Boot
    $299.95
  32. Men's Radford 6-Inch Waterproof Boot Men's Radford 6-Inch Waterproof Boot
    TIMBERLAND Men's Radford 6-Inch Waterproof Boot
    $299.95
  33. Men's Radford 6-Inch Waterproof Boot Men's Radford 6-Inch Waterproof Boot
    TIMBERLAND Men's Radford 6-Inch Waterproof Boot
    $299.95
  34. Men's Adventure 2.0 Alpine Oxford Men's Adventure 2.0 Alpine Oxford
    TIMBERLAND Men's Adventure 2.0 Alpine Oxford
    $229.95
  35. Men's Groveton Plain-Toe Chukka Men's Groveton Plain-Toe Chukka
    TIMBERLAND Men's Groveton Plain-Toe Chukka
    $199.95
  36. Men's Britton Hill Waterproof Wingtip Oxford Boots Men's Britton Hill Waterproof Wingtip Oxford Boots
    TIMBERLAND Men's Britton Hill Waterproof Wingtip Oxford Boots
    From $299.95 $349.95
  37. Men's Britton Hill Waterproof Wingtip Oxford Boots Men's Britton Hill Waterproof Wingtip Oxford Boots
    TIMBERLAND Men's Britton Hill Waterproof Wingtip Oxford Boots
    From $299.95 $349.95
  38. Men's Icon Chelsea Boot Men's Icon Chelsea Boot
    TIMBERLAND Men's Icon Chelsea Boot
    $299.95
  39. Men's Groveton Plain-Toe Chukka Men's Groveton Plain-Toe Chukka
    TIMBERLAND Men's Groveton Plain-Toe Chukka
    $199.95
  40. Men's Adventure 2.0 Cupsole Chukka Men's Adventure 2.0 Cupsole Chukka
    TIMBERLAND Men's Adventure 2.0 Cupsole Chukka
    $259.95
  41. Men's Adventure 2.0 Alpine Oxford Men's Adventure 2.0 Alpine Oxford
    TIMBERLAND Men's Adventure 2.0 Alpine Oxford
    $229.95
  42. Men's Adventure 2.0 Cupsole Chukka Men's Adventure 2.0 Cupsole Chukka
    TIMBERLAND Men's Adventure 2.0 Cupsole Chukka
    $229.95
  43. Men's Adventure 2.0 Cupsole Lea Shoe Men's Adventure 2.0 Cupsole Lea Shoe
    TIMBERLAND Men's Adventure 2.0 Cupsole Lea Shoe
    $229.95
  44. Men's Bradstreet Chukka Men's Bradstreet Chukka
    TIMBERLAND Men's Bradstreet Chukka
    $249.95
  45. Men's Bradstreet Chukka Men's Bradstreet Chukka
    TIMBERLAND Men's Bradstreet Chukka
    $249.95
  46. Men's Bradstreet Oxford Men's Bradstreet Oxford
    TIMBERLAND Men's Bradstreet Oxford
    $229.95
  47. Men's Bradstreet Oxford Men's Bradstreet Oxford
    TIMBERLAND Men's Bradstreet Oxford
    $229.95
  48. Men's 2-Eye Boat Shoe Men's 2-Eye Boat Shoe
    TIMBERLAND Men's 2-Eye Boat Shoe
    From $149 $229.95
  49. Men's Tidelands 3-Eye Boat Shoe Men's Tidelands 3-Eye Boat Shoe
    TIMBERLAND Men's Tidelands 3-Eye Boat Shoe
    $249.95
  50. Men's Tidelands 3-Eye Boat Shoe Men's Tidelands 3-Eye Boat Shoe
    TIMBERLAND Men's Tidelands 3-Eye Boat Shoe
    $249.95
  51. Men's Tidelands Ranger Boat Shoe Men's Tidelands Ranger Boat Shoe
    TIMBERLAND Men's Tidelands Ranger Boat Shoe
    From $119 $249.95
  52. Men's Tidelands Ranger Boat Shoe Men's Tidelands Ranger Boat Shoe
    TIMBERLAND Men's Tidelands Ranger Boat Shoe
    From $119 $249.95
  53. Men's Adventure 2.0 Cupsole Chukka Men's Adventure 2.0 Cupsole Chukka
    TIMBERLAND Men's Adventure 2.0 Cupsole Chukka
    $259.95
  54. Mens Amherst Hi Top Chukka Shoes Mens Amherst Hi Top Chukka Shoes
    TIMBERLAND Mens Amherst Hi Top Chukka Shoes
    From $149 $249.95
  55. Mens Amherst Hi Top Chukka Shoes Mens Amherst Hi Top Chukka Shoes
    TIMBERLAND Mens Amherst Hi Top Chukka Shoes
    From $149 $249.95
  56. Mens Amherst Oxford Shoe Mens Amherst Oxford Shoe
    TIMBERLAND Mens Amherst Oxford Shoe
    From $129 $219.95
  57. Mens Amherst Oxford Shoe Mens Amherst Oxford Shoe
    TIMBERLAND Mens Amherst Oxford Shoe
    From $129 $219.95
  58. Mens Amherst Oxford Shoe Mens Amherst Oxford Shoe
    TIMBERLAND Mens Amherst Oxford Shoe
    From $129 $219.95
  59. Mens Franklin Park Chukka Shoe Mens Franklin Park Chukka Shoe
    TIMBERLAND Mens Franklin Park Chukka Shoe
    From $249.95 $279.95
  60. Mens Franklin Park Chukka Shoe Mens Franklin Park Chukka Shoe
    TIMBERLAND Mens Franklin Park Chukka Shoe
    $279.95