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Welcome to the latest additions in Windsorsmith men's footwear collection. Explore our fresh collection of black leather boots, brown leather boots and tan leather boots, in a range of styles from timeless Chelsea boots, Derby boots and Chukka boots. Discover our range of casual shoes, dress shoes, black leather shoes, brown leather shoes, leather sandals, slides and suede shoes to enhance your style.

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51 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 MARRON LEATHER BOOTS

    WILLEM MARRON LEATHER BOOTS

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

    WILLEM BLACK 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 BLACK LEATHER CHELSEA BOOTS

    WALKER BLACK LEATHER CHELSEA BOOTS

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

    WALKER BROWN OIL SUEDE 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 BROWN OIL SUEDE BOOTS

    GARNER BROWN OIL 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 DARK STONE SUEDE BOOTS

    GARNER DARK STONE SUEDE BOOTS

    Original Price $199.95 Special Price $139.97 30
  15. BRONSON TOBACCO SUEDE SHOES

    BRONSON TOBACCO SUEDE SHOES

    Original Price $159.95 Special Price $111.97 30
  16. BRONSON DARK STONE SUEDE SHOES

    BRONSON DARK STONE SUEDE SHOES

    Original Price $159.95 Special Price $111.97 30
  17. BRONSON WHEAT SUEDE SHOES

    BRONSON WHEAT SUEDE SHOES

    Original Price $159.95 Special Price $111.97 30
  18. BARRET DARK STONE SUEDE BOATSHOES

    BARRET DARK STONE SUEDE BOATSHOES

    Original Price $159.95 Special Price $111.97 30
  19. BARRET CEDAR BOATSHOES

    BARRET CEDAR BOATSHOES

    Original Price $179.95 Special Price $125.97 30
  20. BARRET TOBACCO SUEDE BOATSHOES

    BARRET TOBACCO SUEDE BOATSHOES

    Original Price $159.95 Special Price $111.97 30
  21. ELROY DARK INK SNEAKERS

    ELROY DARK INK SNEAKERS

    Original Price $179.95 Special Price $125.97 30
  22. ELROY CEDAR CASUAL SNEAKERS

    ELROY CEDAR CASUAL SNEAKERS

    Original Price $179.95 Special Price $125.97 30
  23. EDWIN TOBACCO SUEDE SNEAKERS

    EDWIN TOBACCO SUEDE SNEAKERS

    Original Price $179.95 Special Price $125.97 30
  24. EDWIN BLACK SUEDE SNEAKERS

    EDWIN BLACK SUEDE SNEAKERS

    Original Price $179.95 Special Price $125.97 30
  25. EDWIN TAUPE SUEDE SNEAKERS

    EDWIN TAUPE SUEDE SNEAKERS

    Original Price $179.95 Special Price $125.97 30
  26. REY TEAK SUEDE SANDALS

    REY TEAK SUEDE SANDALS

    Original Price $149.95 Special Price $104.97 30
  27. JACE TAUPE SUEDE BOOTS

    JACE TAUPE SUEDE BOOTS

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

    JACE BLACK LEATHER BOOTS

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

    JACE TAN WASHED SUEDE BOOTS

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

    JACE TOBACCO LEATHER BOOTS

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

    JENSEN TAUPE SUEDE BOOTS

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

    JENSEN BLACK LEATHER BOOTS

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

    JENSEN TOBACCO LEATHER BOOTS

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

    JULIUS BLACK LEATHER BOOTS

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

    JULIUS TOBACCO LEATHER BOOTS

    Original Price $199.95 Special Price $139.97 30
  36. AUSTIN T.MORRO LEATHER BOOTS

    AUSTIN T.MORRO LEATHER BOOTS

    Original Price $199.95 Special Price $139.97 30
  37. AUSTIN BLACK LEATHER BOOTS

    AUSTIN BLACK LEATHER BOOTS

    Original Price $199.95 Special Price $139.97 30
  38. FABIAN BLACK LEATHER BOOTS

    FABIAN BLACK LEATHER BOOTS

    Original Price $199.95 Special Price $139.97 30
  39. FABIAN BROWN LEATHER BOOTS

    FABIAN BROWN LEATHER BOOTS

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

    BEAU DARK BROWN LEATHER BOOTS

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

    BEAU BLACK LEATHER BOOTS

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

    BECKETT BLACK LEATHER BOOTS

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

    BECKETT DARK BROWN LEATHER BOOTS

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

    ANSEL BLACK LEATHER BOOTS

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

    ANSEL DARK BROWN LEATHER BOOTS

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

    ABEL BLACK LEATHER BOOTS

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

    ABEL DARK BROWN LEATHER BOOTS

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

    ABEL TAN LEATHER BOOTS

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

    ARLO BLACK LEATHER BOOTS

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

    ARLO DARK BROWN LEATHER BOOTS

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

    ARLO TAN LEATHER BOOTS

    Original Price $199.95 Special Price $139.97 30
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