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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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48 Items

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  1. GRAYSON DARK STONE SUEDE BOOTS

    GRAYSON DARK STONE SUEDE BOOTS

    $199.95
  2. GRAYSON BLACK OIL SUEDE BOOTS

    GRAYSON BLACK OIL SUEDE BOOTS

    $199.95
  3. GRAYSON BROWN OIL SUEDE BOOTS

    GRAYSON BROWN OIL SUEDE BOOTS

    $199.95
  4. WILLEM MARRON LEATHER BOOTS

    WILLEM MARRON LEATHER BOOTS

    $219.95
  5. WILLEM BLACK LEATHER BOOTS

    WILLEM BLACK LEATHER BOOTS

    $219.95
  6. WILLEM BROWN OIL SUEDE BOOTS

    WILLEM BROWN OIL SUEDE BOOTS

    $219.95
  7. GARNER DARK STONE SUEDE BOOTS

    GARNER DARK STONE SUEDE BOOTS

    $199.95
  8. GARNER BLACK OIL SUEDE BOOTS

    GARNER BLACK OIL SUEDE BOOTS

    $199.95
  9. GARNER BROWN OIL SUEDE BOOTS

    GARNER BROWN OIL SUEDE BOOTS

    $199.95
  10. WALKER MARRON LEATHER BOOTS

    WALKER MARRON LEATHER BOOTS

    $219.95
  11. WALKER BROWN OIL SUEDE BOOTS

    WALKER BROWN OIL SUEDE BOOTS

    $219.95
  12. WALKER BLACK LEATHER CHELSEA BOOTS

    WALKER BLACK LEATHER CHELSEA BOOTS

    $219.95
  13. JENSEN TAUPE SUEDE BOOTS

    JENSEN TAUPE SUEDE BOOTS

    $199.95
  14. JENSEN TOBACCO LEATHER BOOTS

    JENSEN TOBACCO LEATHER BOOTS

    $199.95
  15. JENSEN BLACK LEATHER BOOTS

    JENSEN BLACK LEATHER BOOTS

    $199.95
  16. JACE TAUPE SUEDE BOOTS

    JACE TAUPE SUEDE BOOTS

    $199.95
  17. JACE BLACK LEATHER BOOTS

    JACE BLACK LEATHER BOOTS

    $199.95
  18. JACE TOBACCO LEATHER BOOTS

    JACE TOBACCO LEATHER BOOTS

    $199.95
  19. JACE TAN WASHED SUEDE BOOTS

    JACE TAN WASHED SUEDE BOOTS

    $199.95
  20. JULIUS BLACK LEATHER BOOTS

    JULIUS BLACK LEATHER BOOTS

    $199.95
  21. JULIUS TOBACCO LEATHER BOOTS

    JULIUS TOBACCO LEATHER BOOTS

    $199.95
  22. ARLO BLACK LEATHER BOOTS

    ARLO BLACK LEATHER BOOTS

    $199.95
  23. ARLO DARK BROWN LEATHER BOOTS

    ARLO DARK BROWN LEATHER BOOTS

    $199.95
  24. ARLO TAN LEATHER BOOTS

    ARLO TAN LEATHER BOOTS

    $199.95
  25. SERGIO BLACK LEATHER BOOTS

    SERGIO BLACK LEATHER BOOTS

    $199.95
  26. SERGIO DARK BROWN LEATHER BOOTS

    SERGIO DARK BROWN LEATHER BOOTS

    $199.95
  27. SERGIO TAN LEATHER BOOTS

    SERGIO TAN LEATHER BOOTS

    $199.95
  28. BECKETT BLACK LEATHER BOOTS

    BECKETT BLACK LEATHER BOOTS

    $199.95
  29. BECKETT DARK BROWN LEATHER BOOTS

    BECKETT DARK BROWN LEATHER BOOTS

    $199.95
  30. SAXON BROWN OIL SUEDE BOOTS

    SAXON BROWN OIL SUEDE BOOTS

    $169.95
  31. SAXON BLACK OIL SUEDE BOOTS

    SAXON BLACK OIL SUEDE BOOTS

    $169.95
  32. SEBASTIAN BLACK OIL SUEDE LEATHER BOOTS

    SEBASTIAN BLACK OIL SUEDE LEATHER BOOTS

    $169.95
  33. SEBASTIAN BROWN OIL SUEDE BOOTS

    SEBASTIAN BROWN OIL SUEDE BOOTS

    $169.95
  34. SEBASTIAN TAUPE OIL SUEDE LEATHER BOOTS

    SEBASTIAN TAUPE OIL SUEDE LEATHER BOOTS

    $169.95
  35. STEPHAN BLACK LEATHER BOOTS

    STEPHAN BLACK LEATHER BOOTS

    $199.95
  36. STEPHAN DARK BROWN LEATHER BOOTS

    STEPHAN DARK BROWN LEATHER BOOTS

    $199.95
  37. STEPHAN TAN LEATHER BOOTS

    STEPHAN TAN LEATHER BOOTS

    $199.95
  38. BEAU BLACK LEATHER BOOTS

    BEAU BLACK LEATHER BOOTS

    $199.95
  39. BEAU DARK BROWN LEATHER BOOTS

    BEAU DARK BROWN LEATHER BOOTS

    $199.95
  40. ANSEL BLACK LEATHER BOOTS

    ANSEL BLACK LEATHER BOOTS

    $199.95
  41. ANSEL DARK BROWN LEATHER BOOTS

    ANSEL DARK BROWN LEATHER BOOTS

    $199.95
  42. ABEL BLACK LEATHER BOOTS

    ABEL BLACK LEATHER BOOTS

    $199.95
  43. ABEL DARK BROWN LEATHER BOOTS

    ABEL DARK BROWN LEATHER BOOTS

    $199.95
  44. ABEL TAN LEATHER BOOTS

    ABEL TAN LEATHER BOOTS

    $199.95
  45. TRECKKER TAN LEATHER BOOTS

    TRECKKER TAN LEATHER BOOTS

    $219.95
  46. TRECKKER GREY LEATHER BOOTS

    TRECKKER GREY LEATHER BOOTS

    $219.95
  47. URGE COGNAC LEATHER BOOTS

    URGE COGNAC LEATHER BOOTS

    $219.95
  48. URGE BLACK LEATHER BOOTS

    URGE BLACK LEATHER BOOTS

    $219.95
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