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    Classic Shoes

    Here at Samuel Windsor, our collection of men's classic shoes features footwear made only from premium grade leather and suede. Constructed using traditional methods, our classic collection offers a comfortable shoe for every occasion – from formal men's Oxford shoes through to relaxed boat shoes for the weekend.

    Any 2 pairs for $120

    Classic Cheltenham Brogue In Suede - Mid Brown

    Classic Cheltenham Brogue In Suede - Mid Brown

    (30)

    $69.00

    Any 2 pairs for $120

    Classic Chichester Shoe - Black

    Classic Chichester Shoe - Black

    (49)

    $69.00

    Any 2 pairs for $120

    Classic Monk Shoe - Black

    Classic Monk Shoe - Black

    (2366)

    $69.00

    Any 2 pairs for $120

    Classic Monk Shoe - Brown

    Classic Monk Shoe - Brown

    (1618)

    $69.00

    Any 2 pairs for $120

    Classic Penny Loafer Shoe - Black

    Classic Penny Loafer Shoe - Black

    (4020)

    $69.00

    Any 2 pairs for $120

    Classic Penny Loafer - Brown

    Classic Penny Loafer - Brown

    (2091)

    $69.00

    Any 2 pairs for $120

    Classic Semi-Brogue

    Classic Semi-Brogue

    (1660)

    $69.00

    Any 2 pairs for $120

    Classic Oxford Shoe - Brown

    Classic Oxford Shoe - Brown

    (2431)

    $69.00

    Any 2 pairs for $120

    Classic Sandhurst Shoe - Black

    Classic Sandhurst Shoe - Black

    (339)

    $79.00

    Any 2 pairs for $120

    Classic Boat Shoe - Blue

    Classic Boat Shoe - Blue

    (21)

    $69.00

    Any 2 pairs for $120

    Classic Boat Shoe - Tobacco

    Classic Boat Shoe - Tobacco

    (26)

    $69.00

    Any 2 pairs for $120

    Classic Oxblood Cheltenham Brogue

    Classic Oxblood Cheltenham Brogue

    (184)

    $69.00

    Any 2 pairs for $120

    Classic Suede Oxford Shoe

    Classic Suede Oxford Shoe

    (58)

    $69.00

    Any 2 pairs for $120

    Classic Oxford Shoe - Oxblood

    Classic Oxford Shoe - Oxblood

    (211)

    $69.00

    Any 2 pairs for $120

    Classic Oxford Shoe - Mid-Brown

    Classic Oxford Shoe - Mid-Brown

    (158)

    $69.00

    Any 2 pairs for $120

    Classic Oxford Shoe - Tan

    Classic Oxford Shoe - Tan

    (341)

    $69.00

    Any 2 pairs for $120

    Classic Cheltenham Brogue in Suede

    Classic Cheltenham Brogue in Suede

    (114)

    $69.00

    Any 2 pairs for $120

    Classic Sandhurst Shoe

    Classic Sandhurst Shoe

    (1296)

    $69.00

    Any 2 pairs for $120

    Classic Tan Cheltenham Brogue

    Classic Tan Cheltenham Brogue

    (140)

    $69.00

    Any 2 pairs for $120

    Classic Boat Shoe - Navy/Brown

    Classic Boat Shoe - Navy/Brown

    (56)

    $69.00

    Classic Monk Shoe

    Classic Monk Shoe

    (24)

    $59.00

    Any 2 pairs for $120

    Classic Penny Loafer - Black Suede

    Classic Penny Loafer - Black Suede

    (49)

    $69.00

    Any 2 pairs for $120

    Classic Monk Brogue - Black

    Classic Monk Brogue - Black

    (218)

    $69.00

    Any 2 pairs for $120

    Classic Slip-On Boat Shoe

    Classic Slip-On Boat Shoe

    (376)

    $69.00

    Any 2 pairs for $120

    Classic Semi-Brogue - Black

    Classic Semi-Brogue - Black

    (4091)

    $69.00

    Any 2 pairs for $120

    Classic Boat Shoe

    Classic Boat Shoe

    (674)

    $69.00

    Any 2 pairs for $120

    Classic Penny Loafer - Dark Brown Suede

    Classic Penny Loafer - Dark Brown Suede

    (352)

    $69.00

    Any 2 pairs for $120

    Classic Penny Loafer - Brown Suede

    Classic Penny Loafer - Brown Suede

    (928)

    $69.00

    Any 2 pairs for $120

    Classic Oxford Shoe - Black

    Classic Oxford Shoe - Black

    (8041)

    $69.00

    Any 2 pairs for $120

    Classic Quarter-Brogue - Black

    Classic Quarter-Brogue - Black

    (1755)

    $69.00

    Any 2 pairs for $120

    Classic Cheltenham Brogue - Black

    Classic Cheltenham Brogue - Black

    (3052)

    $69.00

    Any 2 pairs for $120

    Classic City Shoe - Black

    Classic City Shoe - Black

    (2911)

    $69.00

    Any 2 pairs for $120

    Classic Kempton Shoe - Black

    Classic Kempton Shoe - Black

    (2015)

    $69.00

    Any 2 pairs for $120

    Classic Kempton Shoe

    Classic Kempton Shoe

    (2565)

    $69.00

    Any 2 pairs for $120

    Classic Moccasin

    Classic Moccasin

    (99)

    $69.00

    Any 2 pairs for $120

    Classic Moccasin - Brown

    Classic Moccasin - Brown

    (22)

    $69.00

    Any 2 pairs for $120

    Classic Suede Driving Shoe

    Classic Suede Driving Shoe

    (99)

    $69.00

    Any 2 pairs for $120

    Classic Durham Shoe - Black

    Classic Durham Shoe - Black

    (108)

    $69.00

    Samuel Windsor

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