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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

Any 2 pairs for $120

Classic Chichester Shoe - Black

Any 2 pairs for $120

Classic Monk Shoe - Black

Any 2 pairs for $120

Classic Monk Shoe - Brown

Any 2 pairs for $120

Classic Penny Loafer Shoe - Black

Any 2 pairs for $120

Classic Penny Loafer - Brown

Any 2 pairs for $120

Classic Semi-Brogue

Classic Semi-Brogue

(1660)

$69.00

Any 2 pairs for $120

Classic Oxford Shoe - Brown

Any 2 pairs for $120

Classic Sandhurst Shoe - Black

Any 2 pairs for $120

Classic Boat Shoe - Blue

Any 2 pairs for $120

Classic Boat Shoe - Tobacco

Any 2 pairs for $120

Classic Oxblood Cheltenham Brogue

Any 2 pairs for $120

Classic Suede Oxford Shoe

Any 2 pairs for $120

Classic Oxford Shoe - Oxblood

Any 2 pairs for $120

Classic Oxford Shoe - Mid-Brown

Any 2 pairs for $120

Classic Oxford Shoe - Tan

Any 2 pairs for $120

Classic Cheltenham Brogue in Suede

Any 2 pairs for $120

Classic Sandhurst Shoe

Classic Sandhurst Shoe

(1296)

$69.00

Any 2 pairs for $120

Classic Tan Cheltenham Brogue

Any 2 pairs for $120

Classic Boat Shoe - Navy/Brown

Classic Monk Shoe

(24)

$59.00

Any 2 pairs for $120

Classic Penny Loafer - Black Suede

Any 2 pairs for $120

Classic Monk Brogue - Black

Any 2 pairs for $120

Classic Slip-On Boat Shoe

Any 2 pairs for $120

Classic Semi-Brogue - Black

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

Any 2 pairs for $120

Classic Penny Loafer - Brown Suede

Any 2 pairs for $120

Classic Oxford Shoe - Black

Any 2 pairs for $120

Classic Quarter-Brogue - Black

Any 2 pairs for $120

Classic Cheltenham Brogue - Black

Any 2 pairs for $120

Classic City Shoe - Black

Any 2 pairs for $120

Classic Kempton Shoe - Black

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

Any 2 pairs for $120

Classic Suede Driving Shoe

Any 2 pairs for $120

Classic Durham Shoe - Black