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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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