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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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46 Items

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  1. WESTON MARRON LEATHER BOOTS

    WESTON MARRON LEATHER BOOTS

    Original Price $219.95 Special Price $153.97 30
  2. WESTON BLACK LEATHER BOOTS

    WESTON BLACK LEATHER BOOTS

    Original Price $219.95 Special Price $153.97 30
  3. WILLEM BLACK LEATHER BOOTS

    WILLEM BLACK LEATHER BOOTS

    Original Price $219.95 Special Price $153.97 30
  4. WILLEM MARRON LEATHER BOOTS

    WILLEM MARRON LEATHER BOOTS

    Original Price $219.95 Special Price $153.97 30
  5. WILLEM BROWN OIL SUEDE BOOTS

    WILLEM BROWN OIL SUEDE BOOTS

    Original Price $219.95 Special Price $153.97 30
  6. WALKER MARRON LEATHER BOOTS

    WALKER MARRON LEATHER BOOTS

    Original Price $219.95 Special Price $153.97 30
  7. WALKER BROWN OIL SUEDE BOOTS

    WALKER BROWN OIL SUEDE BOOTS

    Original Price $219.95 Special Price $153.97 30
  8. WALKER BLACK LEATHER CHELSEA BOOTS

    WALKER BLACK LEATHER CHELSEA BOOTS

    Original Price $219.95 Special Price $153.97 30
  9. GRAYSON DARK STONE SUEDE BOOTS

    GRAYSON DARK STONE SUEDE BOOTS

    Original Price $199.95 Special Price $139.97 30
  10. GRAYSON BLACK OIL SUEDE BOOTS

    GRAYSON BLACK OIL SUEDE BOOTS

    Original Price $199.95 Special Price $139.97 30
  11. GRAYSON BROWN OIL SUEDE BOOTS

    GRAYSON BROWN OIL SUEDE BOOTS

    Original Price $199.95 Special Price $139.97 30
  12. GARNER DARK STONE SUEDE BOOTS

    GARNER DARK STONE SUEDE BOOTS

    Original Price $199.95 Special Price $139.97 30
  13. GARNER BLACK OIL SUEDE BOOTS

    GARNER BLACK OIL SUEDE BOOTS

    Original Price $199.95 Special Price $139.97 30
  14. GARNER BROWN OIL SUEDE BOOTS

    GARNER BROWN OIL SUEDE BOOTS

    Original Price $199.95 Special Price $139.97 30
  15. JENSEN TAUPE SUEDE BOOTS

    JENSEN TAUPE SUEDE BOOTS

    Original Price $199.95 Special Price $139.97 30
  16. JENSEN TOBACCO LEATHER BOOTS

    JENSEN TOBACCO LEATHER BOOTS

    Original Price $199.95 Special Price $139.97 30
  17. JENSEN BLACK LEATHER BOOTS

    JENSEN BLACK LEATHER BOOTS

    Original Price $199.95 Special Price $139.97 30
  18. JACE TAUPE SUEDE BOOTS

    JACE TAUPE SUEDE BOOTS

    Original Price $199.95 Special Price $139.97 30
  19. JACE BLACK LEATHER BOOTS

    JACE BLACK LEATHER BOOTS

    Original Price $199.95 Special Price $139.97 30
  20. JACE TOBACCO LEATHER BOOTS

    JACE TOBACCO LEATHER BOOTS

    Original Price $199.95 Special Price $139.97 30
  21. JACE TAN WASHED SUEDE BOOTS

    JACE TAN WASHED SUEDE BOOTS

    Original Price $199.95 Special Price $139.97 30
  22. JULIUS BLACK LEATHER BOOTS

    JULIUS BLACK LEATHER BOOTS

    Original Price $199.95 Special Price $139.97 30
  23. JULIUS TOBACCO LEATHER BOOTS

    JULIUS TOBACCO LEATHER BOOTS

    Original Price $199.95 Special Price $139.97 30
  24. ARLO BLACK LEATHER BOOTS

    ARLO BLACK LEATHER BOOTS

    Original Price $199.95 Special Price $139.97 30
  25. ARLO DARK BROWN LEATHER BOOTS

    ARLO DARK BROWN LEATHER BOOTS

    Original Price $199.95 Special Price $139.97 30
  26. ARLO TAN LEATHER BOOTS

    ARLO TAN LEATHER BOOTS

    Original Price $199.95 Special Price $139.97 30
  27. SERGIO BLACK LEATHER BOOTS

    SERGIO BLACK LEATHER BOOTS

    Original Price $199.95 Special Price $139.97 30
  28. SERGIO DARK BROWN LEATHER BOOTS

    SERGIO DARK BROWN LEATHER BOOTS

    Original Price $199.95 Special Price $139.97 30
  29. SERGIO TAN LEATHER BOOTS

    SERGIO TAN LEATHER BOOTS

    Original Price $199.95 Special Price $139.97 30
  30. BECKETT BLACK LEATHER BOOTS

    BECKETT BLACK LEATHER BOOTS

    Original Price $199.95 Special Price $139.97 30
  31. BECKETT DARK BROWN LEATHER BOOTS

    BECKETT DARK BROWN LEATHER BOOTS

    Original Price $199.95 Special Price $139.97 30
  32. SAXON BROWN OIL SUEDE BOOTS

    SAXON BROWN OIL SUEDE BOOTS

    Original Price $169.95 Special Price $118.97 30
  33. SAXON BLACK OIL SUEDE BOOTS

    SAXON BLACK OIL SUEDE BOOTS

    Original Price $169.95 Special Price $118.97 30
  34. SEBASTIAN BLACK OIL SUEDE LEATHER BOOTS

    SEBASTIAN BLACK OIL SUEDE LEATHER BOOTS

    Original Price $169.95 Special Price $118.97 30
  35. SEBASTIAN BROWN OIL SUEDE BOOTS

    SEBASTIAN BROWN OIL SUEDE BOOTS

    Original Price $169.95 Special Price $118.97 30
  36. SEBASTIAN TAUPE OIL SUEDE LEATHER BOOTS

    SEBASTIAN TAUPE OIL SUEDE LEATHER BOOTS

    Original Price $169.95 Special Price $118.97 30
  37. STEPHAN BLACK LEATHER BOOTS

    STEPHAN BLACK LEATHER BOOTS

    Original Price $199.95 Special Price $139.97 30
  38. STEPHAN DARK BROWN LEATHER BOOTS

    STEPHAN DARK BROWN LEATHER BOOTS

    Original Price $199.95 Special Price $139.97 30
  39. STEPHAN TAN LEATHER BOOTS

    STEPHAN TAN LEATHER BOOTS

    Original Price $199.95 Special Price $139.97 30
  40. BEAU BLACK LEATHER BOOTS

    BEAU BLACK LEATHER BOOTS

    Original Price $199.95 Special Price $139.97 30
  41. BEAU DARK BROWN LEATHER BOOTS

    BEAU DARK BROWN LEATHER BOOTS

    Original Price $199.95 Special Price $139.97 30
  42. ANSEL BLACK LEATHER BOOTS

    ANSEL BLACK LEATHER BOOTS

    Original Price $199.95 Special Price $139.97 30
  43. ANSEL DARK BROWN LEATHER BOOTS

    ANSEL DARK BROWN LEATHER BOOTS

    Original Price $199.95 Special Price $139.97 30
  44. ABEL BLACK LEATHER BOOTS

    ABEL BLACK LEATHER BOOTS

    Original Price $199.95 Special Price $139.97 30
  45. ABEL DARK BROWN LEATHER BOOTS

    ABEL DARK BROWN LEATHER BOOTS

    Original Price $199.95 Special Price $139.97 30
  46. ABEL TAN LEATHER BOOTS

    ABEL TAN LEATHER BOOTS

    Original Price $199.95 Special Price $139.97 30
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