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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. WILLEM BROWN OIL SUEDE BOOTS

    WILLEM BROWN OIL SUEDE BOOTS

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

    WILLEM BLACK LEATHER BOOTS

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

    WALKER BROWN OIL SUEDE BOOTS

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

    WALKER BLACK LEATHER CHELSEA BOOTS

    Original Price $219.95 Special Price $153.97 30
  5. GRAYSON BROWN OIL SUEDE BOOTS

    GRAYSON BROWN OIL SUEDE BOOTS

    Original Price $199.95 Special Price $139.97 30
  6. GRAYSON BLACK OIL SUEDE BOOTS

    GRAYSON BLACK OIL SUEDE BOOTS

    Original Price $199.95 Special Price $139.97 30
  7. GARNER BLACK OIL SUEDE BOOTS

    GARNER BLACK OIL SUEDE BOOTS

    Original Price $199.95 Special Price $139.97 30
  8. GARNER BROWN OIL SUEDE BOOTS

    GARNER BROWN OIL SUEDE BOOTS

    Original Price $199.95 Special Price $139.97 30
  9. EDWIN TOBACCO SUEDE SNEAKERS

    EDWIN TOBACCO SUEDE SNEAKERS

    Original Price $179.95 Special Price $125.97 30
  10. AUSTIN BLACK LEATHER BOOTS

    AUSTIN BLACK LEATHER BOOTS

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

    AUSTIN T.MORRO LEATHER BOOTS

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

    FABIAN BLACK LEATHER BOOTS

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

    FABIAN BROWN LEATHER BOOTS

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

    JENSEN TAUPE SUEDE BOOTS

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

    JENSEN BLACK LEATHER BOOTS

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

    JENSEN TOBACCO LEATHER BOOTS

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

    JULIUS BLACK LEATHER BOOTS

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

    JULIUS TOBACCO LEATHER BOOTS

    Original Price $199.95 Special Price $139.97 30
  19. JACE TAUPE SUEDE BOOTS

    JACE TAUPE SUEDE BOOTS

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

    JACE BLACK LEATHER BOOTS

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

    JACE TAN WASHED SUEDE BOOTS

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

    JACE TOBACCO LEATHER BOOTS

    Original Price $199.95 Special Price $139.97 30
  23. SAXON BROWN OIL SUEDE BOOTS

    SAXON BROWN OIL SUEDE BOOTS

    Original Price $169.95 Special Price $118.97 30
  24. SAXON BLACK OIL SUEDE BOOTS

    SAXON BLACK OIL SUEDE BOOTS

    Original Price $169.95 Special Price $118.97 30
  25. SEBASTIAN BLACK OIL SUEDE LEATHER BOOTS

    SEBASTIAN BLACK OIL SUEDE LEATHER BOOTS

    Original Price $169.95 Special Price $118.97 30
  26. SEBASTIAN TAUPE OIL SUEDE LEATHER BOOTS

    SEBASTIAN TAUPE OIL SUEDE LEATHER BOOTS

    Original Price $169.95 Special Price $118.97 30
  27. SEBASTIAN BROWN OIL SUEDE BOOTS

    SEBASTIAN BROWN OIL SUEDE BOOTS

    Original Price $169.95 Special Price $118.97 30
  28. BEAU BLACK LEATHER BOOTS

    BEAU BLACK LEATHER BOOTS

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

    BEAU DARK BROWN LEATHER BOOTS

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

    BECKETT BLACK LEATHER BOOTS

    Original Price $199.95 Special Price $139.97 30
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