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92%
112,952

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Most Popular

  1. Classic Oxford Shoe
    £47.95

  2. Classic Cheltenham Brogue
    £47.95

  3. Classic Penny Loafer Shoe
    £47.95

  4. Pleated Chino Trousers
    £17.50

  5. Classic Oxford Shoe
    £47.95

  6. Moleskin Jeans
    £20.00

  7. Classic Monk Shoe
    £47.95

  8. Flat Front Chino
    £17.50

  9. Prestige Oxford Shoe
    £64.95

  10. Classic Semi-Brogue
    £47.95

Prestige Kensington Boot - Rubber Sole

Prestige Kensington Boot - Rubber Sole

£64.95

Typical High Street Price: £150.75

ANY 2 PAIRS £99

Prestige Kensington Boot - Brown, online from Samuel Windsor. Tailored quality at outstanding prices.

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90% (57)
Prestige Kensington Boot - Rubber Sole - Black

Prestige Kensington Boot - Rubber Sole - Black

£64.95

Typical High Street Price: £150.75

ANY 2 PAIRS £99

Prestige Kensington Boot - Black, online from Samuel Windsor. Tailored quality at outstanding prices.

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86% (53)
Prestige Cumbria Boot

Prestige Cumbria Boot

£64.95

Typical High Street Price: £81.00

ANY 2 PAIRS £99

Prestige Cumbria Boot - Mid Brown, a lace-up shoe with an exquisite design and exclusive quality, our prestige range are the epitome of British style and elegance.

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92% (57)
Prestige Country Boot - Rubber Sole

Prestige Country Boot - Rubber Sole

£64.95

Typical High Street Price: £150.75

ANY 2 PAIRS £99

Prestige Country Boot - Antique Tan, online from Samuel Windsor. Tailored quality at outstanding prices.

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94% (55)
Prestige Country Boot - Rubber Sole

Prestige Country Boot - Rubber Sole

£64.95

Typical High Street Price: £150.75

ANY 2 PAIRS £99

Prestige Country Boot, online from Samuel Windsor. Tailored quality at outstanding prices.

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94% (58)
Prestige Belgravia Shoe

Prestige Belgravia Shoe

£64.95

Typical High Street Price: £81.00

ANY 2 PAIRS £99

These nubuck men’s boots are a great addition to any gent’s wardrobe.

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94% (58)
Prestige Chelsea Boot

Prestige Chelsea Boot

£64.95

Typical High Street Price: £150.75

ANY 2 PAIRS £99

Prestige Chelsea Boot, online from Samuel Windsor. Tailored quality at outstanding prices.

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94% (88)
Prestige Chelsea Brogue Boot - Rubber Sole

Prestige Chelsea Brogue Boot - Rubber Sole

£64.95

Typical High Street Price: £150.75

ANY 2 PAIRS £99

Prestige Chelsea Brogue Boot - Rubber Sole is made by hand using Goodyear Welted construction.

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84% (40)
Prestige Chukka Boot - Rubber Sole

Prestige Chukka Boot - Rubber Sole

£64.95

Typical High Street Price: £81.00

ANY 2 PAIRS £99

Buy Prestige Chukka Boots from Samuel Windsor. Rubber soles and Italian leather suede make this classic boot the perfect choice for a smart casual outfit.

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94% (22)
Prestige Chukka Boot - Rubber Sole

Prestige Chukka Boot - Rubber Sole

£64.95

Typical High Street Price: £81.00

ANY 2 PAIRS £99

Buy Burgundy Chukka Boots from Samuel Windsor. Rubber soles and Italian leather suede make this classic boot the perfect choice for a smart casual outfit.

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90% (11)
Prestige Balham Boot - Brown

NEW

Prestige Balham Boot - Brown

£64.95

Typical High Street Price: £81.00

ANY 2 PAIRS £99

Prestige Balham Boot - Brown, online from Samuel Windsor. Tailored quality at outstanding prices.

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80% (1)
Prestige Balham Boot - Black

NEW

Prestige Balham Boot - Black

£64.95

Typical High Street Price: £81.00

ANY 2 PAIRS £99

Prestige Balham Boot - Black, online from Samuel Windsor. Tailored quality at outstanding prices.

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Prestige Chelsea Boot - Black

Prestige Chelsea Boot - Black

£64.95

Typical High Street Price: £150.75

ANY 2 PAIRS £99

Prestige Chelsea Boots: Black, online from Samuel Windsor. Tailored quality at outstanding prices.

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94% (161)
Prestige Suede Chelsea Boot

Prestige Suede Chelsea Boot

£64.95

Typical High Street Price: £150.75

ANY 2 PAIRS £99

Prestige Chelsea Boots: Brown Suede, online from Samuel Windsor. Tailored quality at outstanding prices.

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94% (80)

Samuel Windsor boots are handmade from premium leather and suede. They are available to order in all sizes (including half sizes) from 5 to 14. Our selection includes classics such as desert boots and chukka boots. All of our high quality leather boots can be found in our Prestige range.