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  1. Classic Oxford Shoe
    £47.95

  2. Flat Front Chino
    £15.00

  3. Classic Penny Loafer Shoe
    £47.95

  4. Classic Cheltenham Brogue
    £47.95

  5. Pleated Chino Trousers
    £15.00

  6. Classic Oxford Shoe
    £47.95

  7. Flat Front Chino
    £15.00

  8. Flat Front Chino
    £15.00

  9. Moleskin Jeans
    £20.00

  10. Long Sleeve Weekend Shirt
    £22.50

Classic Semi-Brogue - Black

Classic Semi-Brogue - Black

£47.95

Typical High Street Price: £130.75

ANY TWO FOR £80

Classic Semi-Brogues - Black, online from Samuel Windsor. Tailored quality at outstanding prices.

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94% (165)
Classic Oxford Shoe - Black

Classic Oxford Shoe - Black

£47.95

Typical High Street Price: £130.75

ANY TWO FOR £80

The Samuel Windsor commitment to quality ensures these handmade Classic black Oxford shoes will prove to be the finest, most comfortable and hardest wearing men's leather shoes you will ever invest in.

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92% (838)
Classic Semi-Brogue

Classic Semi-Brogue

£47.95

Typical High Street Price: £130.75

ANY TWO FOR £80

Classic Suede Semi-Brogues - Brown Suede, online from Samuel Windsor. Tailored quality at outstanding prices.

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92% (118)
Classic Quarter-Brogue - Black

Classic Quarter-Brogue - Black

£47.95

Typical High Street Price: £130.75

ANY TWO FOR £80

Classic Plain Toe Cap Quarter Brogue - Black, online from Samuel Windsor. Tailored quality at outstanding prices.

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92% (126)
Classic Monk Shoe - Black

Classic Monk Shoe - Black

£47.95

Typical High Street Price: £132.67

ANY TWO FOR £80

These handmade Monk Shoes is another traditional classic from Samuel Windsor, painstakingly constructed from over 50 natural components. The monk strap leather design is powerful in appearance.

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94% (244)
Classic Monk Shoe

Classic Monk Shoe

£47.95

Typical High Street Price: £132.67

ANY TWO FOR £80

Classic Monk Shoes - Chestnut Brown, online from Samuel Windsor. Tailored quality at outstanding prices.

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90% (153)
Classic Sandhurst Shoe

Classic Sandhurst Shoe

£47.95

Typical High Street Price: £130.75

ANY TWO FOR £80

Classic Sandhurst Shoe - Tan, online from Samuel Windsor. Tailored quality at outstanding prices.

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92% (202)
Classic Sandhurst Shoe - Black

Classic Sandhurst Shoe - Black

£47.95

Typical High Street Price: £130.75

ANY TWO FOR £80

Classic Sandhurst Shoe - Black, online from Samuel Windsor. Tailored quality at outstanding prices.

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90% (62)
Classic Durham Shoe

Classic Durham Shoe

£47.95

Typical High Street Price: £130.75

ANY TWO FOR £80

Classic Durham Shoe - Tan, online from Samuel Windsor. Tailored quality at outstanding prices.

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90% (60)
Classic Penny Loafer

Classic Penny Loafer

£47.95

Typical High Street Price: £132.67

ANY TWO FOR £80

Classic Penny Loafer - Dark Brown Suede, online from Samuel Windsor. Tailored quality at outstanding prices.

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86% (77)
Classic Deck Shoe

Classic Deck Shoe

£47.95

Typical High Street Price: £88.50

ANY TWO FOR £80

Classic Deck Shoe - Brown, online from Samuel Windsor. Tailored quality at outstanding prices.

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90% (138)
Classic Deck Shoe

Classic Deck Shoe

£47.95

Typical High Street Price: £88.50

ANY TWO FOR £80

Classic Deck Shoe in Navy from Samuel Windsor online. Visit us today for discount prices on top quality mens shoes and clothing.

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78% (7)
Classic Derby Shoe

SALE

Classic Derby Shoe

£29.99

Typical High Street Price: £128.00

Save £98.01

Classic Derby Shoe - Blue, online from Samuel Windsor. Tailored quality at outstanding prices.

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88% (68)
Classic Derby Shoe

SALE

Classic Derby Shoe

£29.99

Typical High Street Price: £128.00

Save £98.01

Classic Derby Shoe - Tobacco, online from Samuel Windsor. Tailored quality at outstanding prices.

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94% (50)
Classic Oxford Shoe

Classic Oxford Shoe

£47.95

Typical High Street Price: £130.75

ANY TWO FOR £80

Classic Oxford Shoes - Tan, online from Samuel Windsor. Tailored quality at outstanding prices.

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94% (112)
Classic Slip-On Deck Shoe

Classic Slip-On Deck Shoe

£47.95

Typical High Street Price: £88.50

ANY TWO FOR £80

These Classic Slip-On Boat Shoes are handmade by Samuel Windsor. These designer slip-on shoes are crafted using only the finest leathers.

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86% (135)
Classic Lace-Up Deck Shoe

Classic Lace-Up Deck Shoe

£47.95

Typical High Street Price: £88.50

ANY TWO FOR £80

Our Classic Lace-Up Boat Shoes are handmade by Samuel Windsor. These designer lace-up shoes are crafted using only the finest leathers.

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88% (49)
Classic Oxford Shoe - Cigar

Classic Oxford Shoe - Cigar

£47.95

Typical High Street Price: £130.75

ANY TWO FOR £80

Classic Oxford Shoes - Brown, online from Samuel Windsor. Tailored quality at outstanding prices.

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92% (54)
Classic Semi-Brogue

Classic Semi-Brogue

£47.95

Typical High Street Price: £130.75

ANY TWO FOR £80

Classic Semi-Brogues - Brown, online from Samuel Windsor. Tailored quality at outstanding prices.

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88% (69)
Classic Quarter-Brogue

Classic Quarter-Brogue

£47.95

Typical High Street Price: £130.75

ANY TWO FOR £80

Classic Quarter-Brogues - Brown, online from Samuel Windsor. Tailored quality at outstanding prices.

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92% (39)
Classic Sandhurst Shoe

Classic Sandhurst Shoe

£47.95

Typical High Street Price: £130.75

ANY TWO FOR £80

Classic Sandhurst Shoe - Brown, online from Samuel Windsor. Tailored quality at outstanding prices.

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92% (47)
Classic Driving Shoe

Classic Driving Shoe

£47.95

Typical High Street Price: £76.13

ANY TWO FOR £80

Classic Driving Shoe are comfortable to wear which is perfect for the summer.

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84% (5)
Classic Moccasin

Classic Moccasin

£47.95

Typical High Street Price: £76.13

ANY TWO FOR £80

Made from the finest, soft Italian leather, our Classic moccasins are carefully hand stitched, creating a wonderfully comfortable and durable casual shoe.

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90% (4)
Classic Deck Shoe

Classic Deck Shoe

£47.95

Typical High Street Price: £88.50

ANY TWO FOR £80

Classic Deck Shoe from Samuel Windsor online. Visit us today for discount prices on top quality mens shoes and clothing.

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88% (10)
Classic Durham Shoe

Classic Durham Shoe

£47.95

Typical High Street Price: £130.75

ANY TWO FOR £80

Classic Durham Shoe, online from Samuel Windsor. Tailored quality at outstanding prices.

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88% (45)
Classic Monk Brogue

Classic Monk Brogue

£47.95

Typical High Street Price: £132.67

ANY TWO FOR £80

These monk brogue shoes have been producted using the finest Italian leathers and using a goodyear welted construction which offers and unbeatable combination of durability and comfort and an exceptional price.

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90% (55)
Classic Cheltenham Brogue

Classic Cheltenham Brogue

£47.95

Typical High Street Price: £130.75

ANY TWO FOR £80

Buy classic suede brogues from Samuel Windsor. Our handmade suede brogues offer a casual variation of this classic brogue design.

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94% (33)
Classic Cheltenham Brogue

Classic Cheltenham Brogue

£47.95

Typical High Street Price: £130.75

ANY TWO FOR £80

Buy classic leather brogues. Our handmade tan leather brogues are stylish and comfortable, treading the line perfectly between smart and casual.

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94% (40)
Classic Penny Loafer Shoe - Black

Classic Penny Loafer Shoe - Black

£47.95

Typical High Street Price: £132.67

ANY TWO FOR £80

These black Penny Loafer men's leather shoes from Samuel Windsor are classic formal shoes combined with supple, easy slip-on access.

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90% (413)
Classic Penny Loafer

Classic Penny Loafer

£47.95

Typical High Street Price: £132.67

ANY TWO FOR £80

Classic Penny Loafer Shoe - Chestnut Brown, online from Samuel Windsor. Tailored quality at outstanding prices.

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90% (189)
Classic Oxford Shoe

Classic Oxford Shoe

£47.95

Typical High Street Price: £130.75

ANY TWO FOR £80

Crafted using time honoured shoe making techniques, these Samuel Windsor Classic Oxford Shoes in chestnut brown are classic formal shoes or office shoes.

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94% (294)
Classic City Shoe - Black

Classic City Shoe - Black

£47.95

Typical High Street Price: £128.00

ANY TWO FOR £80

Classic City Shoe - Black, online from Samuel Windsor. Tailored quality at outstanding prices.

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86% (104)
Classic Richmond Shoe - Black

Classic Richmond Shoe - Black

£47.95

Typical High Street Price: £128.00

ANY TWO FOR £80

Great office shoes, these Samuel Windsor Richmond Classics mens black shoes are handmade, incorporating a leather lining which is both breathable and seamless.

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88% (73)
Classic Cheltenham Brogue - Black

Classic Cheltenham Brogue - Black

£47.95

Typical High Street Price: £130.75

ANY TWO FOR £80

Buy classic black brogues. A staple shoe for the modern man, our handmade classic cheltenham brogues are the perfect shoe for formal and casual occasions.

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92% (459)
Classic Kempton Shoe - Black

Classic Kempton Shoe - Black

£47.95

Typical High Street Price: £132.67

ANY TWO FOR £80

Classic Kempton Black Shoe - Slip-On, online from Samuel Windsor. Tailored quality at outstanding prices.

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92% (173)
Classic Kempton Shoe

Classic Kempton Shoe

£47.95

Typical High Street Price: £132.67

ANY TWO FOR £80

Designed to look good with formal or casual wear, these Samuel Windsor real leather Kempton men's leather shoes, men's brown shoes, are an essential addition to any gentleman's wardrobe.

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94% (333)
Nubuck Trainer

SALE

Nubuck Trainer

£27.50

Nubuck Trainer, online from Samuel Windsor. Tailored quality at outstanding prices.

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88% (62)
Casual lace-up

SALE

Casual lace-up

£25.00

Casual Lace Up shoes, online from Samuel Windsor. Tailored quality at outstanding prices.

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88% (53)
Classic Penny Loafer

Classic Penny Loafer

£47.95

Typical High Street Price: £132.67

ANY TWO FOR £80

Classic Penny Loafer Suede, online from Samuel Windsor. Tailored quality at outstanding prices.

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90% (102)

Our classic shoes collection features both formal and casual designs. Samuel Windsor's traditional shoe styles include classic tan Sandhurst shoes, formal chestnut brown Oxfords, brown suede penny loafers and casual blue deck shoes. Order your classic leather and suede shoes today. Available in UK sizes 5 to 14.