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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.

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Sale

Any 2 Pairs for £40 or 3 for £50

Classic Oxford Shoe - Black

Classic Oxford Shoe - Black

(8339)

£27.50 £22.50 Save £5.00

Comparable High Street Price: £144.74

Sale

Any 2 Pairs for £40 or 3 for £50

Classic Cheltenham Brogue - Black

Classic Cheltenham Brogue - Black

(3251)

£27.50 £22.50 Save £5.00

Comparable High Street Price: £96.75

Sale

Any 2 Pairs for £40 or 3 for £50

Classic Penny Loafer Shoe - Black

Classic Penny Loafer Shoe - Black

(4123)

£27.50 £22.50 Save £5.00

Comparable High Street Price: £143.50

Sale

Any 2 Pairs for £40 or 3 for £50

Classic Oxford Shoe - Oxblood

Classic Oxford Shoe - Oxblood

(370)

£27.50 £22.50 Save £5.00

Comparable High Street Price: £144.74

Sale

Any 2 Pairs for £40 or 3 for £50

Classic Cheltenham Brogue - Oxblood

Classic Cheltenham Brogue - Oxblood

(316)

£27.50 £22.50 Save £5.00

Comparable High Street Price: £96.75

Sale

Any 2 Pairs for £40 or 3 for £50

Classic Deck Shoe

Classic Deck Shoe

(750)

£27.50 £22.50 Save £5.00

Comparable High Street Price: £83.25

Sale

Any 2 Pairs for £40 or 3 for £50

Classic Penny Loafer

Classic Penny Loafer

(386)

£27.50 £22.50 Save £5.00

Comparable High Street Price: £143.50

Sale

Any 2 Pairs for £40 or 3 for £50

Classic Kempton Shoe - Black

Classic Kempton Shoe - Black

(2089)

£27.50 £22.50 Save £5.00

Comparable High Street Price: £143.50

Sale

Any 2 Pairs for £40 or 3 for £50

Classic Kempton Shoe

Classic Kempton Shoe

(2654)

£27.50 £22.50 Save £5.00

Comparable High Street Price: £143.50

Sale

Any 2 Pairs for £40 or 3 for £50

Classic Cheltenham Brogue in Suede

Classic Cheltenham Brogue in Suede

(150)

£27.50 £22.50 Save £5.00

Comparable High Street Price: £96.75

Sale

Any 2 Pairs for £40 or 3 for £50

Classic Penny Loafer

Classic Penny Loafer

(961)

£27.50 £22.50 Save £5.00

Comparable High Street Price: £143.50

Sale

Any 2 Pairs for £40 or 3 for £50

Classic Quarter-Brogue - Black

Classic Quarter-Brogue - Black

(1787)

£27.50 £22.50 Save £5.00

Comparable High Street Price: £96.75

Sale

Any 2 Pairs for £40 or 3 for £50

Classic Monk Shoe

Classic Monk Shoe

(1667)

£27.50 £22.50 Save £5.00

Comparable High Street Price: £162.49

Sale

Any 2 Pairs for £40 or 3 for £50

Classic Penny Loafer

Classic Penny Loafer

(2126)

£27.50 £22.50 Save £5.00

Comparable High Street Price: £143.50

Sale

Any 2 Pairs for £40 or 3 for £50

Classic Cheltenham Brogue In Suede - Mid Brown

Classic Cheltenham Brogue In Suede - Mid Brown

(70)

£27.50 £22.50 Save £5.00

Comparable High Street Price: £96.75

Sale

Any 2 Pairs for £40 or 3 for £50

Classic Chichester Shoe - Oxblood

Classic Chichester Shoe - Oxblood

(167)

£27.50 £22.50 Save £5.00

Comparable High Street Price: £144.74

Sale

Any 2 Pairs for £40 or 3 for £50

Classic Penny Loafer

Classic Penny Loafer

(83)

£27.50 £22.50 Save £5.00

Comparable High Street Price: £143.50

Sale

Any 2 Pairs for £40 or 3 for £50

Classic Suede Oxford Shoe

Classic Suede Oxford Shoe

(79)

£27.50 £22.50 Save £5.00

Comparable High Street Price: £144.74

Sale

Any 2 Pairs for £40 or 3 for £50

Classic Derby Shoe - Black

Classic Derby Shoe - Black

(58)

£27.50 £22.50 Save £5.00

Comparable High Street Price: £138.25

Sale

Any 2 Pairs for £40 or 3 for £50

Classic Slip-On Deck Shoe

Classic Slip-On Deck Shoe

(431)

£27.50 £22.50 Save £5.00

Comparable High Street Price: £83.25

Sale

Any 2 Pairs for £40 or 3 for £50

Classic Deck Shoe - Blue

Classic Deck Shoe - Blue

(45)

£27.50 £22.50 Save £5.00

Comparable High Street Price: £83.25

Sale

Any 2 Pairs for £40 or 3 for £50

Classic Moccasin

Classic Moccasin

(119)

£27.50 £22.50 Save £5.00

Comparable High Street Price: £83.75

Sale

Any 2 Pairs for £40 or 3 for £50

Classic Deck Shoe - Tobacco

Classic Deck Shoe - Tobacco

(46)

£27.50 £22.50 Save £5.00

Comparable High Street Price: £83.25

Sale

Any 2 Pairs for £40 or 3 for £50

Classic Leather Driving Shoe

Classic Leather Driving Shoe

(86)

£27.50 £22.50 Save £5.00

Comparable High Street Price: £83.75

Sale

Any 2 Pairs for £40 or 3 for £50

Classic Oxford Shoe

Classic Oxford Shoe

(400)

£27.50 £22.50 Save £5.00

Comparable High Street Price: £144.74

Sale

Any 2 Pairs for £40 or 3 for £50

Classic Driving Shoe

Classic Driving Shoe

(110)

£27.50 £22.50 Save £5.00

Comparable High Street Price: £83.75

Sale

Any 2 Pairs for £40 or 3 for £50

Classic Derby Shoe - Suede

Classic Derby Shoe - Suede

(12)

£27.50 £22.50 Save £5.00

Comparable High Street Price: £138.25

Sale

Any 2 Pairs for £40 or 3 for £50

Classic Sandhurst Shoe - Black

Classic Sandhurst Shoe - Black

(370)

£27.50 £22.50 Save £5.00

Comparable High Street Price: £96.75

Sale

Any 2 Pairs for £40 or 3 for £50

Classic Derby Shoe - Black Suede

Classic Derby Shoe - Black Suede

(19)

£27.50 £22.50 Save £5.00

Comparable High Street Price: £138.25

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