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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. DENZEL BROWN LEATHER SHOES

    DENZEL BROWN LEATHER SHOES

    $189.95
  2. DAMIR BLACK LEATHER SHOES

    DAMIR BLACK LEATHER SHOES

    $169.95
  3. DAMIR BROWN LEATHER SHOES

    DAMIR BROWN LEATHER SHOES

    $179.95
  4. DIEGO BLACK LEATHER SHOES

    DIEGO BLACK LEATHER SHOES

    $169.95
  5. DAVIDE BLACK LEATHER SHOES

    DAVIDE BLACK LEATHER SHOES

    $169.95
  6. DAVIDE BROWN LEATHER SHOES

    DAVIDE BROWN LEATHER SHOES

    $179.95
  7. FRANCIS BLACK LEATHER SHOES

    FRANCIS BLACK LEATHER SHOES

    $129.95
  8. THEO BLACK LEATHER SHOES

    THEO BLACK LEATHER SHOES

    $119.95
  9. EDWIN BLACK SUEDE SNEAKERS

    EDWIN BLACK SUEDE SNEAKERS

    $179.95
  10. EDWIN TOBACCO SUEDE SNEAKERS

    EDWIN TOBACCO SUEDE SNEAKERS

    $179.95
  11. EDWIN TAUPE SUEDE SNEAKERS

    EDWIN TAUPE SUEDE SNEAKERS

    $179.95
  12. CARLO SMOKE LEATHER / SUEDE SHOES

    CARLO SMOKE LEATHER / SUEDE SHOES

    $159.95
  13. CARLO INK LEATHER / SUEDE SHOES

    CARLO INK LEATHER / SUEDE SHOES

    $159.95
  14. CARLO BLACK LEATHER / SUEDE SHOES

    CARLO BLACK LEATHER / SUEDE SHOES

    $159.95
  15. CARLO TOBACCO LEATHER / SUEDE SHOES

    CARLO TOBACCO LEATHER / SUEDE SHOES

    $159.95
  16. CODY MARON SUEDE SHOES

    CODY MARON SUEDE SHOES

    $159.95
  17. HENDRIK KHAKI LEATHER SHOES

    HENDRIK KHAKI LEATHER SHOES

    $189.95
  18. ART157 BLACK LEATHER SHOES

    ART157 BLACK LEATHER SHOES

    $189.95
  19. ART157 GREY LEATHER SHOES

    ART157 GREY LEATHER SHOES

    $189.95
  20. RYAN NAVY CANVAS LOAFERS

    RYAN NAVY CANVAS LOAFERS

    $99.95
  21. ROCCO STEEL SUEDE LOAFERS

    ROCCO STEEL SUEDE LOAFERS

    Original Price $149.95 Special Price $89.97 40
  22. STANLEY BLACK CANVAS SHOES

    STANLEY BLACK CANVAS SHOES

    $89.95
  23. STANLEY ASH CANVAS SHOES

    STANLEY ASH CANVAS SHOES

    $89.95
  24. STANLEY NATURAL CANVAS SHOES

    STANLEY NATURAL CANVAS SHOES

    $89.95
  25. REY TEAK SUEDE SANDALS

    REY TEAK SUEDE SANDALS

    $149.95
  26. REIGN DARK BROWN LEATHER SANDALS

    REIGN DARK BROWN LEATHER SANDALS

    $149.95
  27. REIGN BLACK LEATHER SANDALS

    REIGN BLACK LEATHER SANDALS

    $149.95
  28. RAVEN BLACK LEATHER SANDALS

    RAVEN BLACK LEATHER SANDALS

    $159.95
  29. RAVEN DARK BROWN LEATHER SANDALS

    RAVEN DARK BROWN LEATHER SANDALS

    $159.95
  30. RAMSEY BLACK LEATHER SANDALS

    RAMSEY BLACK LEATHER SANDALS

    $149.95
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