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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

(8142)

£39.95

Comparable High Street Price: £133.49

Any 2 Pairs for £75

Classic Cheltenham Brogue - Black

Classic Cheltenham Brogue - Black

(3116)

£39.95

Comparable High Street Price: £128.49

Any 2 Pairs for £75

Classic Penny Loafer Shoe - Black

Classic Penny Loafer Shoe - Black

(4053)

£39.95

Comparable High Street Price: £113.25

Any 2 Pairs for £75

Classic Oxford Shoe - Oxblood

Classic Oxford Shoe - Oxblood

(264)

£39.95

Comparable High Street Price: £133.49

Any 2 Pairs for £75

Classic Deck Shoe

Classic Deck Shoe

(712)

£39.95

Comparable High Street Price: £93.75

Any 2 Pairs for £75

Classic Oxford Shoe

Classic Oxford Shoe

(2464)

£39.95

Comparable High Street Price: £133.49

Any 2 Pairs for £75

Classic Cheltenham Brogue - Oxblood

Classic Cheltenham Brogue - Oxblood

(228)

£39.95

Comparable High Street Price: £128.49

Any 2 Pairs for £75

Classic Penny Loafer

Classic Penny Loafer

(363)

£39.95

Comparable High Street Price: £113.25

Any 2 Pairs for £75

Classic Kempton Shoe - Black

Classic Kempton Shoe - Black

(2049)

£39.95

Comparable High Street Price: £113.25

Any 2 Pairs for £75

Classic Monk Shoe - Black

Classic Monk Shoe - Black

(2392)

£39.95

Comparable High Street Price: £141.00

Any 2 Pairs for £75

Classic Semi-Brogue - Black

Classic Semi-Brogue - Black

(4106)

£39.95

Comparable High Street Price: £128.49

Any 2 Pairs for £75

Classic Kempton Shoe

Classic Kempton Shoe

(2597)

£39.95

Comparable High Street Price: £113.25

Any 2 Pairs for £75

Classic Deck Shoe - Navy/Brown

Classic Deck Shoe - Navy/Brown

(99)

£39.95

Comparable High Street Price: £93.75

Any 2 Pairs for £75

Classic Chichester Shoe - Black

Classic Chichester Shoe - Black

(71)

£39.95

Comparable High Street Price: £133.49

Any 2 Pairs for £75

Classic Cheltenham Brogue in Suede

Classic Cheltenham Brogue in Suede

(128)

£39.95

Comparable High Street Price: £128.49

Any 2 Pairs for £75

Classic Penny Loafer

Classic Penny Loafer

(944)

£39.95

Comparable High Street Price: £113.25

Any 2 Pairs for £75

Classic Cheltenham Brogue

Classic Cheltenham Brogue

(163)

£39.95

Comparable High Street Price: £128.49

Any 2 Pairs for £75

Classic Monk Brogue - Black

Classic Monk Brogue - Black

(240)

£39.95

Comparable High Street Price: £141.00

Any 2 Pairs for £75

Classic Quarter-Brogue - Black

Classic Quarter-Brogue - Black

(1760)

£39.95

Comparable High Street Price: £128.49

Sale Classic Durham Shoe - Black

Classic Durham Shoe - Black

(137)

£39.95 £25.00 Save £14.95

Comparable High Street Price: £128.49

Any 2 Pairs for £75

Classic Penny Loafer

Classic Penny Loafer

(2103)

£39.95

Comparable High Street Price: £113.25

Any 2 Pairs for £75

Classic Sandhurst Shoe

Classic Sandhurst Shoe

(1311)

£39.95

Comparable High Street Price: £128.49

Any 2 Pairs for £75

Classic City Shoe - Black

Classic City Shoe - Black

(2923)

£39.95

Comparable High Street Price: £128.50

Any 2 Pairs for £75

Classic Cheltenham Brogue In Suede - Mid Brown

Classic Cheltenham Brogue In Suede - Mid Brown

(41)

£39.95

Comparable High Street Price: £128.49

Sale Classic Semi-Brogue

Classic Semi-Brogue

(1665)

£39.95 £27.50 Save £12.45

Comparable High Street Price: £128.49

Any 2 Pairs for £75

Classic Suede Oxford Shoe

Classic Suede Oxford Shoe

(67)

£39.95

Comparable High Street Price: £133.49

Any 2 Pairs for £75

Classic Penny Loafer

Classic Penny Loafer

(62)

£39.95

Comparable High Street Price: £113.25

Sale Classic Oxford Shoe

Classic Oxford Shoe

(176)

£39.95 £27.50 Save £12.45

Comparable High Street Price: £133.49

Sale Classic Sandhurst Shoe - Black

Classic Sandhurst Shoe - Black

(362)

£39.95 £27.50 Save £12.45

Comparable High Street Price: £128.49

Any 2 Pairs for £75

Classic Monk Shoe

Classic Monk Shoe

(1636)

£39.95

Comparable High Street Price: £141.00

Any 2 Pairs for £75

Classic Slip-On Deck Shoe

Classic Slip-On Deck Shoe

(389)

£39.95

Comparable High Street Price: £93.75

Sale Classic Deck Shoe - Blue

Classic Deck Shoe - Blue

(32)

£39.95 £32.50 Save £7.45

Comparable High Street Price: £93.75

Sale Classic Oxford Shoe

Classic Oxford Shoe

(350)

£39.95 £27.50 Save £12.45

Comparable High Street Price: £133.49

Sale Classic Deck Shoe - Tobacco

Classic Deck Shoe - Tobacco

(38)

£39.95 £32.50 Save £7.45

Comparable High Street Price: £93.75

Any 2 Pairs for £75

Classic Lightweight Brogue - Navy

Classic Lightweight Brogue - Navy

(23)

£39.95

Comparable High Street Price: £78.49

Sale Classic Moccasin

Classic Moccasin

(112)

£39.95 £32.50 Save £7.45

Comparable High Street Price: £73.99

Sale Classic Driving Shoe

Classic Driving Shoe

(55)

£39.95 £32.50 Save £7.45

Comparable High Street Price: £73.99

Any 2 Pairs for £75

Classic Moccasin - Brown

Classic Moccasin - Brown

(28)

£39.95

Comparable High Street Price: £73.99

Sale Classic Driving Shoe

Classic Driving Shoe

(108)

£39.95 £32.50 Save £7.45

Comparable High Street Price: £73.99

Any 2 Pairs for £75

Classic Lightweight Brogue - Sand

Classic Lightweight Brogue - Sand

(25)

£39.95

Comparable High Street Price: £78.49

New

Any 2 Pairs for £75

Classic Derby Shoe - Black

Classic Derby Shoe - Black

(1)

£39.95

Comparable High Street Price: £128.50

New

Any 2 Pairs for £75

Classic Chicester Shoe - Oxblood

Classic Chicester Shoe - Oxblood

(0)

£39.95

Comparable High Street Price: £133.49

New

Any 2 Pairs for £75

Classic Derby Shoe - Suede

Classic Derby Shoe - Suede

(0)

£39.95

Comparable High Street Price: £128.50

New

Any 2 Pairs for £75

Classic Derby Shoe - Black Suede

Classic Derby Shoe - Black Suede

(0)

£39.95

Comparable High Street Price: £128.50

New

Any 2 Pairs for £75

Classic Slip-On Deck Shoe - Navy/Brown

Classic Slip-On Deck Shoe - Navy/Brown

(0)

£39.95

Comparable High Street Price: £93.75

New

Any 2 Pairs for £75

Classic Slip-On Deck Shoe - Camel

Classic Slip-On Deck Shoe - Camel

(0)

£39.95

Comparable High Street Price: £93.75

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