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  1. Classic Oxford Shoe
    £47.95

  2. Flat Front Chino
    £15.00

  3. Classic Cheltenham Brogue
    £47.95

  4. Classic Penny Loafer Shoe
    £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

Prestige Kensington Boot - Rubber Sole

Prestige Kensington Boot - Rubber Sole

£59.95

Typical High Street Price: £152.00

Save £92.05

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

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90% (50)
Prestige Kensington Boot - Rubber Sole - Black

Prestige Kensington Boot - Rubber Sole - Black

£59.95

Typical High Street Price: £152.00

Save £92.05

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

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86% (48)
Prestige Cumbria Boot

Prestige Cumbria Boot

£54.95

Typical High Street Price: £81.00

Save £26.05

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% (56)
Prestige Country Boot - Rubber Sole

Prestige Country Boot - Rubber Sole

£59.95

Typical High Street Price: £152.00

Save £92.05

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

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94% (49)
Prestige Country Boot - Rubber Sole

Prestige Country Boot - Rubber Sole

£59.95

Typical High Street Price: £152.00

Save £92.05

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

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92% (50)
Prestige Belgravia Shoe

Prestige Belgravia Shoe

£54.95

Typical High Street Price: £81.00

Save £26.05

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

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94% (62)
Prestige Chelsea Boot

Prestige Chelsea Boot

£54.95

Typical High Street Price: £152.00

Save £97.05

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

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94% (86)
Prestige Chelsea Brogue Boot - Rubber Sole

Prestige Chelsea Brogue Boot - Rubber Sole

£59.95

Typical High Street Price: £152.00

Save £92.05

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

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86% (42)
Prestige Chukka Boot - Rubber Sole

Prestige Chukka Boot - Rubber Sole

£54.95

Typical High Street Price: £81.00

Save £26.05

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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92% (28)
Prestige Chukka Boot - Rubber Sole

Prestige Chukka Boot - Rubber Sole

£54.95

Typical High Street Price: £81.00

Save £26.05

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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92% (19)
Prestige Balham Boot - Brown

NEW

Prestige Balham Boot - Brown

£54.95

Typical High Street Price: £81.00

Save £26.05

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

£54.95

Typical High Street Price: £81.00

Save £26.05

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

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no reviews
Prestige Chelsea Boot - Black

Prestige Chelsea Boot - Black

£54.95

Typical High Street Price: £152.00

Save £97.05

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

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94% (157)
Prestige Suede Chelsea Boot

Prestige Suede Chelsea Boot

£54.95

Typical High Street Price: £152.00

Save £97.05

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

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94% (75)

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.