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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 £75

Classic Oxford Shoe - Black

Classic Oxford Shoe - Black

(8041)

£39.95

Typical High Street Price: £133.74

Any 2 pairs for £75

Classic Cheltenham Brogue - Black

Classic Cheltenham Brogue - Black

(3052)

£39.95

Typical High Street Price: £127.24

Any 2 pairs for £75

Classic Penny Loafer Shoe - Black

Classic Penny Loafer Shoe - Black

(4020)

£39.95

Typical High Street Price: £112.98

Any 2 pairs for £75

Classic Oxford Shoe - Oxblood

Classic Oxford Shoe - Oxblood

(211)

£39.95

Typical High Street Price: £133.74

Any 2 pairs for £75

Classic Oxford Shoe

Classic Oxford Shoe

(2431)

£39.95

Typical High Street Price: £133.74

Any 2 pairs for £75

Classic Deck Shoe

Classic Deck Shoe

(674)

£39.95

Typical High Street Price: £94.75

Any 2 pairs for £75

Classic Cheltenham Brogue

Classic Cheltenham Brogue

(184)

£39.95

Typical High Street Price: £127.24

Any 2 pairs for £75

Classic Penny Loafer

Classic Penny Loafer

(352)

£39.95

Typical High Street Price: £112.98

Any 2 pairs for £75

Classic Monk Shoe - Black

Classic Monk Shoe - Black

(2366)

£39.95

Typical High Street Price: £153.00

Any 2 pairs for £75

Classic Chichester Shoe - Black

Classic Chichester Shoe - Black

(49)

£39.95

Typical High Street Price: £133.74

Any 2 pairs for £75

Classic Kempton Shoe - Black

Classic Kempton Shoe - Black

(2015)

£39.95

Typical High Street Price: £112.98

Any 2 pairs for £75

Classic Semi-Brogue - Black

Classic Semi-Brogue - Black

(4091)

£39.95

Typical High Street Price: £127.24

Any 2 pairs for £75

Classic Kempton Shoe

Classic Kempton Shoe

(2565)

£39.95

Typical High Street Price: £112.98

Any 2 pairs for £75

Classic Cheltenham Brogue in Suede

Classic Cheltenham Brogue in Suede

(114)

£39.95

Typical High Street Price: £127.24

Any 2 pairs for £75

Classic Monk Brogue - Black

Classic Monk Brogue - Black

(218)

£39.95

Typical High Street Price: £153.00

Any 2 pairs for £75

Classic Penny Loafer

Classic Penny Loafer

(928)

£39.95

Typical High Street Price: £112.98

Any 2 pairs for £75

Classic Quarter-Brogue - Black

Classic Quarter-Brogue - Black

(1755)

£39.95

Typical High Street Price: £127.24

Any 2 pairs for £75

Classic Cheltenham Brogue

Classic Cheltenham Brogue

(140)

£39.95

Typical High Street Price: £127.24

Any 2 pairs for £75

Classic Sandhurst Shoe

Classic Sandhurst Shoe

(1296)

£39.95

Typical High Street Price: £127.24

Any 2 pairs for £75

Classic City Shoe - Black

Classic City Shoe - Black

(2911)

£39.95

Typical High Street Price: £114.98

Any 2 pairs for £75

Classic Penny Loafer

Classic Penny Loafer

(2091)

£39.95

Typical High Street Price: £112.98

New

Any 2 pairs for £75

Classic Deck Shoe - Navy/Brown

Classic Deck Shoe - Navy/Brown

(56)

£39.95

Typical High Street Price: £94.75

Any 2 pairs for £75

Classic Suede Oxford Shoe

Classic Suede Oxford Shoe

(58)

£39.95

Typical High Street Price: £133.74

Any 2 pairs for £75

Classic Cheltenham Brogue In Suede - Mid Brown

Classic Cheltenham Brogue In Suede - Mid Brown

(30)

£39.95

Typical High Street Price: £127.24

Any 2 pairs for £75

Classic Semi-Brogue

Classic Semi-Brogue

(1660)

£39.95

Typical High Street Price: £127.24

Any 2 pairs for £75

Classic Monk Shoe

Classic Monk Shoe

(1618)

£39.95

Typical High Street Price: £153.00

Any 2 pairs for £75

Classic Penny Loafer

Classic Penny Loafer

(49)

£39.95

Typical High Street Price: £112.98

Any 2 pairs for £75

Classic Durham Shoe - Black

Classic Durham Shoe - Black

(108)

£39.95

Typical High Street Price: £127.24

Any 2 pairs for £75

Classic Oxford Shoe

Classic Oxford Shoe

(158)

£39.95

Typical High Street Price: £133.74

Any 2 pairs for £75

Classic Slip-On Deck Shoe

Classic Slip-On Deck Shoe

(376)

£39.95

Typical High Street Price: £94.75

Any 2 pairs for £75

Classic Sandhurst Shoe - Black

Classic Sandhurst Shoe - Black

(339)

£39.95

Typical High Street Price: £127.24

Any 2 pairs for £75

Classic Oxford Shoe

Classic Oxford Shoe

(341)

£39.95

Typical High Street Price: £133.74

New

Any 2 pairs for £75

Classic Deck Shoe - Blue

Classic Deck Shoe - Blue

(21)

£39.95

Typical High Street Price: £94.75

New

Any 2 pairs for £75

Classic Moccasin

Classic Moccasin

(99)

£39.95

Typical High Street Price: £67.24

New

Any 2 pairs for £75

Classic Deck Shoe - Tobacco

Classic Deck Shoe - Tobacco

(26)

£39.95

Typical High Street Price: £94.75

New

Any 2 pairs for £75

Classic Moccasin - Brown

Classic Moccasin - Brown

(22)

£39.95

Typical High Street Price: £67.24

New

Any 2 pairs for £75

Classic Driving Shoe

Classic Driving Shoe

(43)

£39.95

Typical High Street Price: £67.24

New

Any 2 pairs for £75

Classic Driving Shoe

Classic Driving Shoe

(99)

£39.95

Typical High Street Price: £67.24

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