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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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158 Items

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  1. SAXON BROWN OIL SUEDE BOOTS

    SAXON BROWN OIL SUEDE BOOTS

    $169.95
  2. SAXON BLACK OIL SUEDE BOOTS

    SAXON BLACK OIL SUEDE BOOTS

    $169.95
  3. HUNTER BLACK LEATHER BOOTS

    HUNTER BLACK LEATHER BOOTS

    $229.95
  4. SEBASTIAN BLACK OIL SUEDE LEATHER BOOTS

    SEBASTIAN BLACK OIL SUEDE LEATHER BOOTS

    $169.95
  5. SEBASTIAN TAUPE OIL SUEDE LEATHER BOOTS

    SEBASTIAN TAUPE OIL SUEDE LEATHER BOOTS

    $169.95
  6. SEBASTIAN BROWN OIL SUEDE LEATHER BOOTS

    SEBASTIAN BROWN OIL SUEDE LEATHER BOOTS

    $169.95
  7. BEAU BLACK LEATHER BOOTS

    BEAU BLACK LEATHER BOOTS

    $199.95
  8. BEAU DARK BROWN LEATHER BOOTS

    BEAU DARK BROWN LEATHER BOOTS

    $199.95
  9. BECKETT BLACK LEATHER BOOTS

    BECKETT BLACK LEATHER BOOTS

    $199.95
  10. BECKETT DARK BROWN LEATHER BOOTS

    BECKETT DARK BROWN LEATHER BOOTS

    $199.95
  11. ANSEL BLACK LEATHER BOOTS

    ANSEL BLACK LEATHER BOOTS

    $199.95
  12. ANSEL DARK BROWN LEATHER BOOTS

    ANSEL DARK BROWN LEATHER BOOTS

    $199.95
  13. ARLO BLACK LEATHER BOOTS

    ARLO BLACK LEATHER BOOTS

    $199.95
  14. ARLO DARK BROWN LEATHER BOOTS

    ARLO DARK BROWN LEATHER BOOTS

    $199.95
  15. ARLO TAN LEATHER BOOTS

    ARLO TAN LEATHER BOOTS

    $199.95
  16. ABEL BLACK LEATHER BOOTS

    ABEL BLACK LEATHER BOOTS

    $199.95
  17. ABEL DARK BROWN LEATHER BOOTS

    ABEL DARK BROWN LEATHER BOOTS

    $199.95
  18. ABEL TAN LEATHER BOOTS

    ABEL TAN LEATHER BOOTS

    $199.95
  19. ORION BLACK LEATHER BOOTS

    ORION BLACK LEATHER BOOTS

    $249.95
  20. DANIELE BLACK LEATHER BOOTS

    DANIELE BLACK LEATHER BOOTS

    $199.95
  21. DANIELE BLACK/NATURAL LEATHER BOOTS

    DANIELE BLACK/NATURAL LEATHER BOOTS

    $199.95
  22. DANIELE DARK BROWN LEATHER BOOTS

    DANIELE DARK BROWN LEATHER BOOTS

    $219.95
  23. STEPHAN BLACK LEATHER BOOTS

    STEPHAN BLACK LEATHER BOOTS

    $199.95
  24. STEPHAN DARK BROWN LEATHER BOOTS

    STEPHAN DARK BROWN LEATHER BOOTS

    $199.95
  25. STEPHAN TAN LEATHER BOOTS

    STEPHAN TAN LEATHER BOOTS

    $199.95
  26. SERGIO BLACK LEATHER BOOTS

    SERGIO BLACK LEATHER BOOTS

    $199.95
  27. SERGIO DARK BROWN LEATHER BOOTS

    SERGIO DARK BROWN LEATHER BOOTS

    $199.95
  28. SERGIO TAN LEATHER BOOTS

    SERGIO TAN LEATHER BOOTS

    $199.95
  29. NIALL BLACK LEATHER BOOTS

    NIALL BLACK LEATHER BOOTS

    $199.95
  30. NIALL BROWN LEATHER BOOTS

    NIALL BROWN LEATHER BOOTS

    $199.95
  31. MATTEO BLACK LEATHER BOOTS

    MATTEO BLACK LEATHER BOOTS

    $199.95
  32. MATTEO BROWN LEATHER BOOTS

    MATTEO BROWN LEATHER BOOTS

    $199.95
  33. GEORGE BLACK LEATHER BOOTS

    GEORGE BLACK LEATHER BOOTS

    $199.95
  34. GEORGE BROWN LEATHER BOOTS

    GEORGE BROWN LEATHER BOOTS

    $199.95
  35. Men's Black wedding dress boot

    STOCKMAN BLACK LEATHER BOOTS

    $229.95
  36. Men's Brown Dress Boot Wedding Groomsmen

    STOCKMAN T.MORRO LEATHER BOOTS

    $229.95
  37. Men's dress shoes

    MARI BLACK LEATHER BOOTS

    $189.95
  38. CORNELL BLACK LEATHER BOOTS

    CORNELL BLACK LEATHER BOOTS

    $189.95
  39. CORNELL BROWN LEATHER BOOTS

    CORNELL BROWN LEATHER BOOTS

    $189.95
  40. SAMUEL MARON SUEDE BOOTS

    SAMUEL MARON SUEDE BOOTS

    $179.95
  41. FEVERR BLACK LEATHER BOOTS

    FEVERR BLACK LEATHER BOOTS

    $229.95
  42. FEVERR COGNAC LEATHER BOOTS

    FEVERR COGNAC LEATHER BOOTS

    $229.95
  43. AIDAN BLACK LEATHER BOOTS

    AIDAN BLACK LEATHER BOOTS

    $229.95
  44. AIDAN DARK BROWN LEATHER BOOTS

    AIDAN DARK BROWN LEATHER BOOTS

    $229.95
  45. JUSTIN COGNAC LEATHER BOOTS

    JUSTIN COGNAC LEATHER BOOTS

    $229.95
  46. KRAB BLACK LEATHER BOOTS

    KRAB BLACK LEATHER BOOTS

    $189.95
  47. KRAB BROWN LEATHER BOOTS

    KRAB BROWN LEATHER BOOTS

    $189.95
  48. MYLES BLACK LEATHER BOOTS

    MYLES BLACK LEATHER BOOTS

    $199.95
  49. MYLES BROWN LEATHER BOOTS

    MYLES BROWN LEATHER BOOTS

    $199.95
  50. HOBB BLACK LEATHER BOOTS

    HOBB BLACK LEATHER BOOTS

    $189.95
  51. HOBB BROWN LEATHER BOOTS

    HOBB BROWN LEATHER BOOTS

    $189.95
  52. TOORAK SUEDE BLACK BOOTS

    TOORAK SUEDE BLACK BOOTS

    $179.95
  53. TOORAK SUEDE NAVY SUEDE BOOTS

    TOORAK SUEDE NAVY SUEDE BOOTS

    $179.95
  54. TOORAK SUEDE MARON BOOTS

    TOORAK SUEDE MARON BOOTS

    $179.95
  55. DENZEL BLACK LEATHER SHOES

    DENZEL BLACK LEATHER SHOES

    $179.95
  56. PEARSON BLACK LEATHER SHOES

    PEARSON BLACK LEATHER SHOES

    $129.95
  57. DENZEL BROWN LEATHER SHOES

    DENZEL BROWN LEATHER SHOES

    $189.95
  58. PITT BLACK PATENT SHOES

    PITT BLACK PATENT SHOES

    $169.95
  59. DAMIR BLACK LEATHER SHOES

    DAMIR BLACK LEATHER SHOES

    $169.95
  60. DAMIR BROWN LEATHER SHOES

    DAMIR BROWN LEATHER SHOES

    $179.95
  61. DIEGO BLACK LEATHER SHOES

    DIEGO BLACK LEATHER SHOES

    $169.95
  62. DAVIDE BLACK LEATHER SHOES

    DAVIDE BLACK LEATHER SHOES

    $169.95
  63. DAVIDE BROWN LEATHER SHOES

    DAVIDE BROWN LEATHER SHOES

    $179.95
  64. FRANCIS BLACK LEATHER SHOES

    FRANCIS BLACK LEATHER SHOES

    $129.95
  65. OSBORNE BLACK LEATHER SHOES

    OSBORNE BLACK LEATHER SHOES

    $179.95
  66. THEO BLACK LEATHER

    THEO BLACK LEATHER

    $119.95
  67. ROCKET BLACK LEATHER SHOES

    ROCKET BLACK LEATHER SHOES

    $149.95
  68. SAUL BLACK LEATHER SHOES

    SAUL BLACK LEATHER SHOES

    $159.95
  69. LUCA BLACK LEATHER SHOES

    LUCA BLACK LEATHER SHOES

    $169.95
  70. NOAH BLACK LEATHER SHOES

    NOAH BLACK LEATHER SHOES

    $169.95
  71. NOAH BROWN LEATHER SHOES

    NOAH BROWN LEATHER SHOES

    $169.95
  72. Men's black lace-up dress shoe for grooms and groomsmen.

    HARRY BLACK LEATHER SHOES

    $189.95
  73. Men's Tan Cognac Dress Shoes - side view. Windsor Smith

    HARRY COGNAC LEATHER SHOES

    $189.95
  74. Men's brown derby brogue shoes on side view - Edward by Windsor Smith

    EDWARD COGNAC SHOES

    $199.95
  75. DEREK BLACK LEATHER SHOES

    DEREK BLACK LEATHER SHOES

    $189.95
  76. DEREK CAMEL LEATHER SHOES

    DEREK CAMEL LEATHER SHOES

    $189.95
  77. JAGGER BLACK LEATHER SHOES

    JAGGER BLACK LEATHER SHOES

    $119.95
  78. JAKE BLACK LEATHER SHOES

    JAKE BLACK LEATHER SHOES

    $119.95
  79. WASSP NAVY SUEDE LOAFERS

    WASSP NAVY SUEDE LOAFERS

    $189.95
  80. WASSP TOBACCO SUEDE LOAFERS

    WASSP TOBACCO SUEDE LOAFERS

    $189.95
  81. URGE BLACK LEATHER BOOTS

    URGE BLACK LEATHER BOOTS

    $219.95
  82. URGE COGNAC LEATHER BOOTS

    URGE COGNAC LEATHER BOOTS

    $219.95
  83. TRECKKER TAN LEATHER BOOTS

    TRECKKER TAN LEATHER BOOTS

    $219.95
  84. TRECKKER GREY LEATHER BOOTS

    TRECKKER GREY LEATHER BOOTS

    $219.95
  85. WILL BLUE LEATHER SHOES

    WILL BLUE LEATHER SHOES

    $199.95
  86. WILL KHAKI LEATHER SHOES

    WILL KHAKI LEATHER SHOES

    $199.95
  87. BOSTON MARON SUEDE SHOES

    BOSTON MARON SUEDE SHOES

    $159.95
  88. BOSTON TRUE NAVY SUEDE SHOES

    BOSTON TRUE NAVY SUEDE SHOES

    $159.95
  89. BRONX NAVY CANVAS SHOES

    BRONX NAVY CANVAS SHOES

    $99.95
  90. CARLO BLACK LEATHER / SUEDE SHOES

    CARLO BLACK LEATHER / SUEDE SHOES

    $159.95
  91. CARLO SMOKE LEATHER / SUEDE SHOES

    CARLO SMOKE LEATHER / SUEDE SHOES

    $159.95
  92. CARLO INK LEATHER / SUEDE SHOES

    CARLO INK LEATHER / SUEDE SHOES

    $159.95
  93. CARLO TOBACCO LEATHER / SUEDE SHOES

    CARLO TOBACCO LEATHER / SUEDE SHOES

    $159.95
  94. CODY MARON SUEDE SHOES

    CODY MARON SUEDE SHOES

    $159.95
  95. TATE BLUE LEATHER SHOES

    TATE BLUE LEATHER SHOES

    $199.95
  96. TATE KHAKI LEATHER SHOES

    TATE KHAKI LEATHER SHOES

    $199.95
  97. CEDRIC NAVY CANVAS SHOES

    CEDRIC NAVY CANVAS SHOES

    $199.95
  98. CEDRIC KHAKI CANVAS SHOES

    CEDRIC KHAKI CANVAS SHOES

    $199.95
  99. HENDRIK TAN LEATHER SHOES

    HENDRIK TAN LEATHER SHOES

    $189.95
  100. HENDRIK KHAKI LEATHER SHOES

    HENDRIK KHAKI LEATHER SHOES

    $189.95
  101. 369 NAVY LEATHER LOAFERS

    369 NAVY LEATHER LOAFERS

    $179.95
  102. 369 BROWN LEATHER LOAFERS

    369 BROWN LEATHER LOAFERS

    $179.95
  103. 369 TAUPE LEATHER LOAFERS

    369 TAUPE LEATHER LOAFERS

    $179.95
  104. CARTER TAN LEATHER SHOES

    CARTER TAN LEATHER SHOES

    $199.95
  105. ART157 TAN LEATHER SHOES

    ART157 TAN LEATHER SHOES

    $189.95
  106. ART157 BLACK LEATHER SHOES

    ART157 BLACK LEATHER SHOES

    $189.95
  107. ART157 GREY LEATHER SHOES

    ART157 GREY LEATHER SHOES

    $189.95
  108. RYAN NAVY CANVAS LOAFERS

    RYAN NAVY CANVAS LOAFERS

    $99.95
  109. ROCCO NAVY SUEDE LOAFERS

    ROCCO NAVY SUEDE LOAFERS

    $149.95
  110. ROCCO STEEL SUEDE LOAFERS

    ROCCO STEEL SUEDE LOAFERS

    $149.95
  111. SCOTT NAVY SUEDE SHOES

    SCOTT NAVY SUEDE SHOES

    $119.95
  112. SCOTT FAWN SUEDE SHOES

    SCOTT FAWN SUEDE SHOES

    $119.95
  113. STANLEY BLACK CANVAS SHOES

    STANLEY BLACK CANVAS SHOES

    $89.95
  114. STANLEY ASH CANVAS SHOES

    STANLEY ASH CANVAS SHOES

    $89.95
  115. STANLEY NATURAL CANVAS SHOES

    STANLEY NATURAL CANVAS SHOES

    $89.95
  116. RAVEN BLACK LEATHER SANDALS

    RAVEN BLACK LEATHER SANDALS

    $159.95
  117. RAVEN DARK BROWN LEATHER SANDALS

    RAVEN DARK BROWN LEATHER SANDALS

    $159.95
  118. REIGN BLACK LEATHER SANDALS

    REIGN BLACK LEATHER SANDALS

    $149.95
  119. REIGN DARK BROWN LEATHER SANDALS

    REIGN DARK BROWN LEATHER SANDALS

    $149.95
  120. RAMSEY BLACK LEATHER SANDALS

    RAMSEY BLACK LEATHER SANDALS

    $149.95
  121. RAMSEY DARK BROWN LEATHER SANDALS

    RAMSEY DARK BROWN LEATHER SANDALS

    $149.95
  122. RIVER BLACK LEATHER SANDALS

    RIVER BLACK LEATHER SANDALS

    $149.95
  123. RIVER DARK BROWN LEATHER SANDALS

    RIVER DARK BROWN LEATHER SANDALS

    $149.95
  124. ROWDY BLACK LEATHER SANDALS

    ROWDY BLACK LEATHER SANDALS

    $149.95
  125. ROWDY DARK BROWN LEATHER SANDALS

    ROWDY DARK BROWN LEATHER SANDALS

    $149.95
  126. I don't give a fuck, mens white socks.

    NOVELTY SOCK I DON'T GIVE A F*CK

    $9.95
  127. Who's your daddy socks

    NOVELTY SOCK WHO'S YOUR DADDY

    $9.95
  128. White sport socks with No Bullshit - the bull is a logo - Windsor Smith

    NOVELTY SOCK NO BULLSH*T

    $9.95
  129. White Mother F*cker Sock in display packaging

    NOVELTY SOCK MOTHER F*CKER

    $9.95
  130. MEN'S CREW SOCK WHITE

    MEN'S CREW SOCK WHITE

    $9.95
  131. MEN'S LOW CUT SOCK WHITE

    MEN'S LOW CUT SOCK WHITE

    $7.95
  132. TRUE RIB MEN'S DRESS SOCK BLACK

    TRUE RIB MEN'S DRESS SOCK BLACK

    $12.95
  133. WINDOW CHECK MEN'S DRESS SOCK NAVY

    WINDOW CHECK MEN'S DRESS SOCK NAVY

    $12.95
  134. ARGYLE MEN'S DRESS SOCK GREY MARLE

    ARGYLE MEN'S DRESS SOCK GREY MARLE

    $12.95
  135. MEN'S INVISIBLE SOCK 3PK MULTI COLOUR

    MEN'S INVISIBLE SOCK 3PK MULTI COLOUR

    $19.95
  136. AUSTIN JEAN BELT BLACK LEATHER

    AUSTIN JEAN BELT BLACK LEATHER

    $69.95
  137. ALEC REVERSIBLE BELT BLACK/WHISKEY

    ALEC REVERSIBLE BELT BLACK/WHISKEY

    $79.95
  138. MEN'S DRESS BELT BLACK LEATHER

    MEN'S DRESS BELT BLACK LEATHER

    $79.95
  139. MEN'S DRESS BELT WHISKY LEATHER

    MEN'S DRESS BELT WHISKY LEATHER

    $79.95
  140. LOUIS JEAN BELT BLACK LEATHER

    LOUIS JEAN BELT BLACK LEATHER

    $69.95
  141. LOUIS JEAN BELT CHOCOLATE LEATHER

    LOUIS JEAN BELT CHOCOLATE LEATHER

    $69.95
  142. LOUIS JEAN BELT TAN LEATHER

    LOUIS JEAN BELT TAN LEATHER

    $69.95
  143. LACHLAN WALLET TAN LEATHER

    LACHLAN WALLET TAN LEATHER

    $79.95
  144. LAKEN CARD HOLDER TAN LEATHER

    LAKEN CARD HOLDER TAN LEATHER

    $39.95
  145. MENS DRESS 90CM BLACK 90cm

    MENS DRESS 90CM BLACK 90cm

    $3.95
  146. MENS DRESS 90CM BROWN 90cm

    MENS DRESS 90CM BROWN 90cm

    $3.95
  147. ECO WATER PROOFER

    ECO WATER PROOFER

    $15.95
  148. ESSENTIAL CREAM LEATHER BALM

    ESSENTIAL CREAM LEATHER BALM

    $12.00
  149. LIQUID SHOE POLISH BOTTLE

    SELF SHINE LIQUID RENO POLISH - -

    $5.00
  150. SUEDE BRUSH - -

    SUEDE BRUSH - -

    $8.00
  151. Clear gel heel shields

    WS GEL HEEL SHIELDS - -

    $10.00
  152. WS ANTI SLIP HEEL GRIP - -

    WS ANTI SLIP HEEL GRIP - -

    $10.00
  153. RENOVATING POLISH BLACK 45G - -

    RENOVATING POLISH BLACK 45G - -

    $10.00
  154. RENOVATING POLISH NEUTRAL 45G - -

    RENOVATING POLISH NEUTRAL 45G - -

    $10.00
  155. WS DUBBIN POLISH - -

    WS DUBBIN POLISH - -

    $10.00
  156. WS WAXY OILY SPONGE - -

    WS WAXY OILY SPONGE - -

    $12.00
  157. WS EXPRESS SHINE SPONGE - -

    WS EXPRESS SHINE SPONGE - -

    $8.00
  158. SUEDE AND NUBUCK SHAMPOO 55ML - -

    SUEDE AND NUBUCK SHAMPOO 55ML - -

    $8.00
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