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Welcome to the Windsorsmith Men's Shoes and Boots Collection. Explore our classic and timeless range of premium leather shoes, including black men's leather shoes, men's leather boots and leather slides. From dress shoes to Chelsea boots, Derby shoes to Oxford lace-up shoes, we offer a variety of styles to suit every occasion. Embrace sophistication with our selection of brown shoes and tan shoes, perfect for any occasion. Complete your ensemble with our smart casual sneakers, canvas slip-ons and loafers. Upgrade your footwear game with Windsorsmith.

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  1. BOSTON TRUE NAVY SUEDE SHOES

    BOSTON TRUE NAVY SUEDE SHOES

    $159.95
  2. BRONX NAVY CANVAS SHOES

    BRONX NAVY CANVAS SHOES

    $99.95
  3. CARLO BLACK LEATHER / SUEDE SHOES

    CARLO BLACK LEATHER / SUEDE SHOES

    $159.95
  4. CARLO SMOKE LEATHER / SUEDE SHOES

    CARLO SMOKE LEATHER / SUEDE SHOES

    $159.95
  5. CARLO INK LEATHER / SUEDE SHOES

    CARLO INK LEATHER / SUEDE SHOES

    $159.95
  6. CARLO TOBACCO LEATHER / SUEDE SHOES

    CARLO TOBACCO LEATHER / SUEDE SHOES

    $159.95
  7. CODY MARON SUEDE SHOES

    CODY MARON SUEDE SHOES

    $159.95
  8. TATE BLUE LEATHER SHOES

    TATE BLUE LEATHER SHOES

    $199.95
  9. TATE KHAKI LEATHER SHOES

    TATE KHAKI LEATHER SHOES

    $199.95
  10. CEDRIC NAVY CANVAS SHOES

    CEDRIC NAVY CANVAS SHOES

    $199.95
  11. CEDRIC KHAKI CANVAS SHOES

    CEDRIC KHAKI CANVAS SHOES

    $199.95
  12. HENDRIK TAN LEATHER SHOES

    HENDRIK TAN LEATHER SHOES

    $189.95
  13. HENDRIK KHAKI LEATHER SHOES

    HENDRIK KHAKI LEATHER SHOES

    $189.95
  14. 369 NAVY LEATHER LOAFERS

    369 NAVY LEATHER LOAFERS

    $179.95
  15. 369 BROWN LEATHER LOAFERS

    369 BROWN LEATHER LOAFERS

    $179.95
  16. 369 TAUPE LEATHER LOAFERS

    369 TAUPE LEATHER LOAFERS

    $179.95
  17. EDWIN TAUPE SUEDE SNEAKERS

    EDWIN TAUPE SUEDE SNEAKERS

    $179.95
  18. CARTER TAN LEATHER SHOES

    CARTER TAN LEATHER SHOES

    $199.95
  19. ART157 TAN LEATHER SHOES

    ART157 TAN LEATHER SHOES

    $189.95
  20. ART157 BLACK LEATHER SHOES

    ART157 BLACK LEATHER SHOES

    $189.95
  21. ART157 GREY LEATHER SHOES

    ART157 GREY LEATHER SHOES

    $189.95
  22. RYAN NAVY CANVAS LOAFERS

    RYAN NAVY CANVAS LOAFERS

    $99.95
  23. ROCCO NAVY SUEDE LOAFERS

    ROCCO NAVY SUEDE LOAFERS

    $149.95
  24. ROCCO STEEL SUEDE LOAFERS

    ROCCO STEEL SUEDE LOAFERS

    $149.95
  25. STANLEY BLACK CANVAS SHOES

    STANLEY BLACK CANVAS SHOES

    $89.95
  26. STANLEY ASH CANVAS SHOES

    STANLEY ASH CANVAS SHOES

    $89.95
  27. STANLEY NATURAL CANVAS SHOES

    STANLEY NATURAL CANVAS SHOES

    $89.95
  28. REY TEAK SUEDE SANDALS

    REY TEAK SUEDE SANDALS

    $149.95
  29. REIGN DARK BROWN LEATHER SANDALS

    REIGN DARK BROWN LEATHER SANDALS

    $149.95
  30. REIGN BLACK LEATHER SANDALS

    REIGN BLACK LEATHER SANDALS

    $149.95
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