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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. STANLEY NATURAL CANVAS SHOES

    STANLEY NATURAL CANVAS SHOES

    Original Price $89.95 Special Price $62.97 30
  2. REY TEAK SUEDE SANDALS

    REY TEAK SUEDE SANDALS

    Original Price $149.95 Special Price $104.97 30
  3. REIGN DARK BROWN LEATHER SANDALS

    REIGN DARK BROWN LEATHER SANDALS

    Original Price $149.95 Special Price $104.97 30
  4. REIGN BLACK LEATHER SANDALS

    REIGN BLACK LEATHER SANDALS

    Original Price $149.95 Special Price $104.97 30
  5. RAVEN BLACK LEATHER SANDALS

    RAVEN BLACK LEATHER SANDALS

    Original Price $159.95 Special Price $111.97 30
  6. RAVEN DARK BROWN LEATHER SANDALS

    RAVEN DARK BROWN LEATHER SANDALS

    Original Price $159.95 Special Price $111.97 30
  7. RAMSEY BLACK LEATHER SANDALS

    RAMSEY BLACK LEATHER SANDALS

    Original Price $149.95 Special Price $104.97 30
  8. RAMSEY DARK BROWN LEATHER SANDALS

    RAMSEY DARK BROWN LEATHER SANDALS

    Original Price $149.95 Special Price $104.97 30
  9. RIVER BLACK LEATHER SANDALS

    RIVER BLACK LEATHER SANDALS

    Original Price $149.95 Special Price $104.97 30
  10. RIVER DARK BROWN LEATHER SANDALS

    RIVER DARK BROWN LEATHER SANDALS

    Original Price $149.95 Special Price $104.97 30
  11. ROWDY BLACK LEATHER SANDALS

    ROWDY BLACK LEATHER SANDALS

    Original Price $149.95 Special Price $104.97 30
  12. ROWDY DARK BROWN LEATHER SANDALS

    ROWDY DARK BROWN LEATHER SANDALS

    Original Price $149.95 Special Price $104.97 30
  13. I don't give a fuck, mens white socks.

    NOVELTY SOCK I DON'T GIVE A F*CK

    Original Price $9.95 Special Price $6.97 30
  14. Who's your daddy socks

    NOVELTY SOCK WHO'S YOUR DADDY

    Original Price $9.95 Special Price $6.97 30
  15. White sport socks with No Bullshit - the bull is a logo - Windsor Smith

    NOVELTY SOCK NO BULLSH*T

    Original Price $9.95 Special Price $6.97 30
  16. White Mother F*cker Sock in display packaging

    NOVELTY SOCK MOTHER F*CKER

    Original Price $9.95 Special Price $6.97 30
  17. MEN'S CREW SOCK WHITE

    MEN'S CREW SOCK WHITE

    Original Price $9.95 Special Price $6.97 30
  18. MEN'S LOW CUT SOCK WHITE

    MEN'S LOW CUT SOCK WHITE

    Original Price $7.95 Special Price $5.57 30
  19. WINDOW CHECK MEN'S DRESS SOCK NAVY

    WINDOW CHECK MEN'S DRESS SOCK NAVY

    Original Price $12.95 Special Price $9.07 30
  20. ARGYLE MEN'S DRESS SOCK GREY MARLE

    ARGYLE MEN'S DRESS SOCK GREY MARLE

    Original Price $12.95 Special Price $9.07 30
  21. MEN'S INVISIBLE SOCK 3PK MULTI COLOUR

    MEN'S INVISIBLE SOCK 3PK MULTI COLOUR

    Original Price $19.95 Special Price $13.97 30
  22. AUSTIN JEAN BELT BLACK LEATHER

    AUSTIN JEAN BELT BLACK LEATHER

    Original Price $69.95 Special Price $48.97 30
  23. ALEC REVERSIBLE BELT BLACK/WHISKEY

    ALEC REVERSIBLE BELT BLACK/WHISKEY

    Original Price $79.95 Special Price $55.97 30
  24. MEN'S DRESS BELT BLACK LEATHER

    MEN'S DRESS BELT BLACK LEATHER

    Original Price $79.95 Special Price $55.97 30
  25. MEN'S DRESS BELT WHISKY LEATHER

    MEN'S DRESS BELT WHISKY LEATHER

    Original Price $79.95 Special Price $55.97 30
  26. LOUIS JEAN BELT BLACK LEATHER

    LOUIS JEAN BELT BLACK LEATHER

    Original Price $69.95 Special Price $48.97 30
  27. LOUIS JEAN BELT CHOCOLATE LEATHER

    LOUIS JEAN BELT CHOCOLATE LEATHER

    Original Price $69.95 Special Price $48.97 30
  28. LOUIS JEAN BELT TAN LEATHER

    LOUIS JEAN BELT TAN LEATHER

    Original Price $69.95 Special Price $48.97 30
  29. LACHLAN WALLET TAN LEATHE one siz

    LACHLAN WALLET TAN LEATHE one siz

    Original Price $79.95 Special Price $55.97 30
  30. MENS DRESS 90CM BLACK 90cm

    MENS DRESS 90CM BLACK 90cm

    Original Price $3.95 Special Price $2.77 30
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