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113,189

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  1. Classic Oxford Shoe
    £47.95

  2. Classic Cheltenham Brogue
    £47.95

  3. Pleated Chino Trousers
    £17.50

  4. Classic Penny Loafer Shoe
    £47.95

  5. Classic Oxford Shoe
    £47.95

  6. Moleskin Jeans
    £20.00

  7. Flat Front Chino
    £17.50

  8. Classic Tweed Jacket
    £69.00

  9. Prestige Oxford Shoe
    £64.95

  10. Classic Monk Shoe
    £47.95

Classic Monk Shoe - Black

Classic Monk Shoe - Black

£47.95

Typical High Street Price: £131.00

ANY 2 PAIRS £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% (248)
Classic Monk Shoe

Classic Monk Shoe

£47.95

Typical High Street Price: £131.00

ANY 2 PAIRS £80

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

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90% (158)
Prestige Tasselled Loafer - Black

Prestige Tasselled Loafer - Black

£64.95

Typical High Street Price: £131.00

ANY 2 PAIRS £99

Prestige Tasselled Loafer - Black, online from Samuel Windsor. Tailored quality at outstanding prices.

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92% (68)
Prestige Tasselled Suede Loafer

Prestige Tasselled Suede Loafer

£64.95

Typical High Street Price: £131.00

ANY 2 PAIRS £99

Prestige Tasselled Loafer - Blue Suede, online from Samuel Windsor. Tailored quality at outstanding prices.

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88% (45)
Classic Penny Loafer

Classic Penny Loafer

£47.95

Typical High Street Price: £131.00

ANY 2 PAIRS £80

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

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84% (79)
Prestige Penny Loafer - Black

Prestige Penny Loafer - Black

£64.95

Typical High Street Price: £131.00

ANY 2 PAIRS £99

Prestige Penny Loafer - Black, online from Samuel Windsor. Tailored quality at outstanding prices.

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90% (80)
Prestige Penny Loafer

Prestige Penny Loafer

£64.95

Typical High Street Price: £131.00

ANY 2 PAIRS £99

Prestige Penny Loafer - Brown, online from Samuel Windsor. Tailored quality at outstanding prices.

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90% (72)
Prestige Monk Shoe - Rubber Sole - Black

Prestige Monk Shoe - Rubber Sole - Black

£64.95

Typical High Street Price: £106.17

ANY 2 PAIRS £99

Prestige Monk Shoe - Black, online from Samuel Windsor. Tailored quality at outstanding prices.

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92% (32)
Prestige Slip-On Deck Shoe

Prestige Slip-On Deck Shoe

£64.95

Typical High Street Price: £111.00

ANY 2 PAIRS £99

Prestige Leather Slip-On Boat Shoe - made with the finest Italian leather uppers or a luxury finish and unbeatable comfort and durability.

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90% (126)
Classic Slip-On Deck Shoe

Classic Slip-On Deck Shoe

£47.95

Typical High Street Price: £88.50

ANY 2 PAIRS £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% (159)
Prestige Slip-On Deck Shoe

Prestige Slip-On Deck Shoe

£64.95

Typical High Street Price: £111.00

ANY 2 PAIRS £99

Our Prestige Slip-on Boat Shoes with contrasting colours is the epitome of casual sophistication. Visit us now for great offers on leather deck shoes.

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88% (138)
Prestige Tasselled Loafer

Prestige Tasselled Loafer

£64.95

Typical High Street Price: £131.00

ANY 2 PAIRS £99

Prestige Tasselled Loafer - Brown, online from Samuel Windsor. Tailored quality at outstanding prices.

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76% (23)
Classic Driving Shoe

Classic Driving Shoe

£47.95

Typical High Street Price: £80.00

ANY 2 PAIRS £80

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

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Classic Moccasin

Classic Moccasin

£47.95

Typical High Street Price: £80.00

ANY 2 PAIRS £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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100% (2)
Prestige Twin Monk

Prestige Twin Monk

£64.95

Typical High Street Price: £131.00

ANY 2 PAIRS £99

Prestige Twin Monk, online from Samuel Windsor. Tailored quality at outstanding prices.

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88% (60)
Classic Monk Brogue

Classic Monk Brogue

£47.95

Typical High Street Price: £131.00

ANY 2 PAIRS £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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92% (51)
Classic Penny Loafer Shoe - Black

Classic Penny Loafer Shoe - Black

£47.95

Typical High Street Price: £131.00

ANY 2 PAIRS £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% (420)
Classic Penny Loafer

Classic Penny Loafer

£47.95

Typical High Street Price: £131.00

ANY 2 PAIRS £80

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

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90% (196)
Classic Kempton Shoe - Black

Classic Kempton Shoe - Black

£47.95

Typical High Street Price: £131.00

ANY 2 PAIRS £80

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

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92% (175)
Classic Kempton Shoe

Classic Kempton Shoe

£47.95

Typical High Street Price: £131.00

ANY 2 PAIRS £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% (337)
Classic Penny Loafer

Classic Penny Loafer

£47.95

Typical High Street Price: £131.00

ANY 2 PAIRS £80

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

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90% (102)

These luxury leather slip-on shoes are available to order in sizes from 5 to 14. Find a pair for every occasion, there's tasselled loafers for going out in town and leather slippers for lounging about at home. Need shoes for more formal occasions? Don't miss our Oxford shoes, Brogues and Derbys plus many more in the Samuel Windsor lace ups collection.