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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. CARLO SMOKE LEATHER / SUEDE SHOES

    CARLO SMOKE LEATHER / SUEDE SHOES

    Original Price $159.95 Special Price $111.97 30
  2. CARLO INK LEATHER / SUEDE SHOES

    CARLO INK LEATHER / SUEDE SHOES

    Original Price $159.95 Special Price $111.97 30
  3. CARLO BLACK LEATHER / SUEDE SHOES

    CARLO BLACK LEATHER / SUEDE SHOES

    Original Price $159.95 Special Price $111.97 30
  4. CARLO TOBACCO LEATHER / SUEDE SHOES

    CARLO TOBACCO LEATHER / SUEDE SHOES

    Original Price $159.95 Special Price $111.97 30
  5. WILL BLUE LEATHER SHOES

    WILL BLUE LEATHER SHOES

    Original Price $199.95 Special Price $139.97 30
  6. WILL KHAKI LEATHER SHOES

    WILL KHAKI LEATHER SHOES

    Original Price $199.95 Special Price $139.97 30
  7. BOSTON MARON SUEDE SHOES

    BOSTON MARON SUEDE SHOES

    Original Price $159.95 Special Price $111.97 30
  8. BOSTON TRUE NAVY SUEDE SHOES

    BOSTON TRUE NAVY SUEDE SHOES

    Original Price $159.95 Special Price $111.97 30
  9. BRONX NAVY CANVAS SHOES

    BRONX NAVY CANVAS SHOES

    Original Price $99.95 Special Price $69.97 30
  10. CODY MARON SUEDE SHOES

    CODY MARON SUEDE SHOES

    Original Price $159.95 Special Price $111.97 30
  11. TATE BLUE LEATHER SHOES

    TATE BLUE LEATHER SHOES

    Original Price $199.95 Special Price $139.97 30
  12. TATE KHAKI LEATHER SHOES

    TATE KHAKI LEATHER SHOES

    Original Price $199.95 Special Price $139.97 30
  13. HENDRIK TAN LEATHER SHOES

    HENDRIK TAN LEATHER SHOES

    Original Price $189.95 Special Price $132.97 30
  14. HENDRIK KHAKI LEATHER SHOES

    HENDRIK KHAKI LEATHER SHOES

    Original Price $189.95 Special Price $132.97 30
  15. 369 NAVY LEATHER LOAFERS

    369 NAVY LEATHER LOAFERS

    Original Price $179.95 Special Price $125.97 30
  16. 369 TAUPE LEATHER LOAFERS

    369 TAUPE LEATHER LOAFERS

    Original Price $179.95 Special Price $125.97 30
  17. 369 BROWN LEATHER LOAFERS

    369 BROWN LEATHER LOAFERS

    Original Price $179.95 Special Price $125.97 30
  18. URGE BLACK LEATHER BOOTS

    URGE BLACK LEATHER BOOTS

    Original Price $219.95 Special Price $153.97 30
  19. URGE COGNAC LEATHER BOOTS

    URGE COGNAC LEATHER BOOTS

    Original Price $219.95 Special Price $153.97 30
  20. TRECKKER TAN LEATHER BOOTS

    TRECKKER TAN LEATHER BOOTS

    Original Price $219.95 Special Price $153.97 30
  21. TRECKKER GREY LEATHER BOOTS

    TRECKKER GREY LEATHER BOOTS

    Original Price $219.95 Special Price $153.97 30
  22. CARTER TAN LEATHER SHOES

    CARTER TAN LEATHER SHOES

    Original Price $199.95 Special Price $139.97 30
  23. ART157 TAN LEATHER SHOES

    ART157 TAN LEATHER SHOES

    Original Price $189.95 Special Price $132.97 30
  24. ART157 BLACK LEATHER SHOES

    ART157 BLACK LEATHER SHOES

    Original Price $189.95 Special Price $132.97 30
  25. ART157 GREY LEATHER SHOES

    ART157 GREY LEATHER SHOES

    Original Price $189.95 Special Price $132.97 30
  26. RYAN NAVY CANVAS LOAFERS

    RYAN NAVY CANVAS LOAFERS

    Original Price $99.95 Special Price $69.97 30
  27. ROCCO NAVY SUEDE LOAFERS

    ROCCO NAVY SUEDE LOAFERS

    Original Price $149.95 Special Price $104.97 30
  28. ROCCO STEEL SUEDE LOAFERS

    ROCCO STEEL SUEDE LOAFERS

    Original Price $149.95 Special Price $104.97 30
  29. STANLEY BLACK CANVAS SHOES

    STANLEY BLACK CANVAS SHOES

    Original Price $89.95 Special Price $62.97 30
  30. STANLEY ASH CANVAS SHOES

    STANLEY ASH CANVAS SHOES

    Original Price $89.95 Special Price $62.97 30
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