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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. JAKE BLACK LEATHER SHOES

    JAKE BLACK LEATHER SHOES

    $119.95
  2. PEARSON BLACK LEATHER SHOES

    PEARSON BLACK LEATHER SHOES

    $129.95
  3. PITT BLACK PATENT SHOES

    PITT BLACK PATENT SHOES

    $169.95
  4. HUNTER BLACK LEATHER BOOTS

    HUNTER BLACK LEATHER BOOTS

    $229.95
  5. SEBASTIAN BLACK OIL SUEDE LEATHER BOOTS

    SEBASTIAN BLACK OIL SUEDE LEATHER BOOTS

    $169.95
  6. SEBASTIAN TAUPE OIL SUEDE LEATHER BOOTS

    SEBASTIAN TAUPE OIL SUEDE LEATHER BOOTS

    $169.95
  7. SEBASTIAN BROWN OIL SUEDE LEATHER BOOTS

    SEBASTIAN BROWN OIL SUEDE LEATHER BOOTS

    $169.95
  8. BEAU BLACK LEATHER BOOTS

    BEAU BLACK LEATHER BOOTS

    $199.95
  9. BEAU DARK BROWN LEATHER BOOTS

    BEAU DARK BROWN LEATHER BOOTS

    $199.95
  10. BECKETT BLACK LEATHER BOOTS

    BECKETT BLACK LEATHER BOOTS

    $199.95
  11. BECKETT DARK BROWN LEATHER BOOTS

    BECKETT DARK BROWN LEATHER BOOTS

    $199.95
  12. ANSEL BLACK LEATHER BOOTS

    ANSEL BLACK LEATHER BOOTS

    $199.95
  13. ANSEL DARK BROWN LEATHER BOOTS

    ANSEL DARK BROWN LEATHER BOOTS

    $199.95
  14. ARLO BLACK LEATHER BOOTS

    ARLO BLACK LEATHER BOOTS

    $199.95
  15. ARLO DARK BROWN LEATHER BOOTS

    ARLO DARK BROWN LEATHER BOOTS

    $199.95
  16. ARLO TAN LEATHER BOOTS

    ARLO TAN LEATHER BOOTS

    $199.95
  17. ABEL BLACK LEATHER BOOTS

    ABEL BLACK LEATHER BOOTS

    $199.95
  18. ABEL DARK BROWN LEATHER BOOTS

    ABEL DARK BROWN LEATHER BOOTS

    $199.95
  19. ABEL TAN LEATHER BOOTS

    ABEL TAN LEATHER BOOTS

    $199.95
  20. ORION BLACK LEATHER BOOTS

    ORION BLACK LEATHER BOOTS

    $249.95
  21. DANIELE BLACK LEATHER BOOTS

    DANIELE BLACK LEATHER BOOTS

    $199.95
  22. DANIELE BLACK/NATURAL LEATHER BOOTS

    DANIELE BLACK/NATURAL LEATHER BOOTS

    $199.95
  23. DANIELE DARK BROWN LEATHER BOOTS

    DANIELE DARK BROWN LEATHER BOOTS

    $219.95
  24. STEPHAN BLACK LEATHER BOOTS

    STEPHAN BLACK LEATHER BOOTS

    $199.95
  25. STEPHAN DARK BROWN LEATHER BOOTS

    STEPHAN DARK BROWN LEATHER BOOTS

    $199.95
  26. STEPHAN TAN LEATHER BOOTS

    STEPHAN TAN LEATHER BOOTS

    $199.95
  27. SERGIO BLACK LEATHER BOOTS

    SERGIO BLACK LEATHER BOOTS

    $199.95
  28. SERGIO DARK BROWN LEATHER BOOTS

    SERGIO DARK BROWN LEATHER BOOTS

    $199.95
  29. SERGIO TAN LEATHER BOOTS

    SERGIO TAN LEATHER BOOTS

    $199.95
  30. NIALL BLACK LEATHER BOOTS

    NIALL BLACK LEATHER BOOTS

    $199.95
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