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Casual Boots

Welcome to Windsorsmith men's Casual Boots collection. Browse our selection of versatile leather boots, including Chelsea boots, Derby boots and Chukka boots. Browse our range of classic black leather boots, timeless tan leather boots or step into our elegant brown leather boots. Whether you're dressing up or down, our boots offer the perfect blend of style and functionality for any occasion.

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43 Items

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  1. SAXON BROWN OIL SUEDE BOOTS

    SAXON BROWN OIL SUEDE BOOTS

    $169.95
  2. SAXON BLACK OIL SUEDE BOOTS

    SAXON BLACK OIL SUEDE BOOTS

    $169.95
  3. HUNTER BLACK LEATHER BOOTS

    HUNTER BLACK LEATHER BOOTS

    $229.95
  4. SEBASTIAN BROWN OIL SUEDE LEATHER BOOTS

    SEBASTIAN BROWN OIL SUEDE LEATHER BOOTS

    $169.95
  5. SEBASTIAN BLACK OIL SUEDE LEATHER BOOTS

    SEBASTIAN BLACK OIL SUEDE LEATHER BOOTS

    $169.95
  6. SEBASTIAN TAUPE OIL SUEDE LEATHER BOOTS

    SEBASTIAN TAUPE OIL SUEDE LEATHER BOOTS

    $169.95
  7. STEPHAN BLACK LEATHER BOOTS

    STEPHAN BLACK LEATHER BOOTS

    $199.95
  8. STEPHAN DARK BROWN LEATHER BOOTS

    STEPHAN DARK BROWN LEATHER BOOTS

    $199.95
  9. STEPHAN TAN LEATHER BOOTS

    STEPHAN TAN LEATHER BOOTS

    $199.95
  10. ARLO BLACK LEATHER BOOTS

    ARLO BLACK LEATHER BOOTS

    $199.95
  11. ARLO DARK BROWN LEATHER BOOTS

    ARLO DARK BROWN LEATHER BOOTS

    $199.95
  12. ARLO TAN LEATHER BOOTS

    ARLO TAN LEATHER BOOTS

    $199.95
  13. FEVERR COGNAC LEATHER BOOTS

    FEVERR COGNAC LEATHER BOOTS

    $229.95
  14. FEVERR BLACK LEATHER BOOTS

    FEVERR BLACK LEATHER BOOTS

    $229.95
  15. BECKETT BLACK LEATHER BOOTS

    BECKETT BLACK LEATHER BOOTS

    $199.95
  16. BECKETT DARK BROWN LEATHER BOOTS

    BECKETT DARK BROWN LEATHER BOOTS

    $199.95
  17. BEAU BLACK LEATHER BOOTS

    BEAU BLACK LEATHER BOOTS

    $199.95
  18. BEAU DARK BROWN LEATHER BOOTS

    BEAU DARK BROWN LEATHER BOOTS

    $199.95
  19. ANSEL BLACK LEATHER BOOTS

    ANSEL BLACK LEATHER BOOTS

    $199.95
  20. ANSEL DARK BROWN LEATHER BOOTS

    ANSEL DARK BROWN LEATHER BOOTS

    $199.95
  21. ABEL BLACK LEATHER BOOTS

    ABEL BLACK LEATHER BOOTS

    $199.95
  22. ABEL DARK BROWN LEATHER BOOTS

    ABEL DARK BROWN LEATHER BOOTS

    $199.95
  23. ABEL TAN LEATHER BOOTS

    ABEL TAN LEATHER BOOTS

    $199.95
  24. AIDAN BLACK LEATHER BOOTS

    AIDAN BLACK LEATHER BOOTS

    $229.95
  25. AIDAN DARK BROWN LEATHER BOOTS

    AIDAN DARK BROWN LEATHER BOOTS

    $229.95
  26. JUSTIN COGNAC LEATHER BOOTS

    JUSTIN COGNAC LEATHER BOOTS

    $229.95
  27. KRAB BLACK LEATHER BOOTS

    KRAB BLACK LEATHER BOOTS

    $189.95
  28. KRAB BROWN LEATHER BOOTS

    KRAB BROWN LEATHER BOOTS

    $189.95
  29. SERGIO BLACK LEATHER BOOTS

    SERGIO BLACK LEATHER BOOTS

    $199.95
  30. SERGIO DARK BROWN LEATHER BOOTS

    SERGIO DARK BROWN LEATHER BOOTS

    $199.95
  31. SERGIO TAN LEATHER BOOTS

    SERGIO TAN LEATHER BOOTS

    $199.95
  32. CORNELL BLACK LEATHER BOOTS

    CORNELL BLACK LEATHER BOOTS

    $189.95
  33. CORNELL BROWN LEATHER BOOTS

    CORNELL BROWN LEATHER BOOTS

    $189.95
  34. SAMUEL MARON SUEDE BOOTS

    SAMUEL MARON SUEDE BOOTS

    $179.95
  35. HOBB BLACK LEATHER BOOTS

    HOBB BLACK LEATHER BOOTS

    $189.95
  36. HOBB BROWN LEATHER BOOTS

    HOBB BROWN LEATHER BOOTS

    $189.95
  37. TOORAK SUEDE BLACK BOOTS

    TOORAK SUEDE BLACK BOOTS

    $179.95
  38. TOORAK SUEDE NAVY SUEDE BOOTS

    TOORAK SUEDE NAVY SUEDE BOOTS

    $179.95
  39. TOORAK SUEDE MARON BOOTS

    TOORAK SUEDE MARON BOOTS

    $179.95
  40. TRECKKER TAN LEATHER BOOTS

    TRECKKER TAN LEATHER BOOTS

    $219.95
  41. TRECKKER GREY LEATHER BOOTS

    TRECKKER GREY LEATHER BOOTS

    $219.95
  42. URGE COGNAC LEATHER BOOTS

    URGE COGNAC LEATHER BOOTS

    $219.95
  43. URGE BLACK LEATHER BOOTS

    URGE BLACK LEATHER BOOTS

    $219.95
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