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  1. Classic Oxford Shoe
    £37.50

  2. Classic Cheltenham Brogue
    £37.50

  3. Classic Penny Loafer Shoe
    £37.50

  4. Classic Oxford Shoe
    £37.50

  5. Classic Monk Shoe
    £37.50

  6. Classic Semi-Brogue
    £37.50

  7. Classic Penny Loafer
    £37.50

  8. Classic Penny Loafer
    £37.50

  9. Classic Sandhurst Shoe
    £37.50

  10. Classic Kempton Shoe
    £37.50

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% (44)
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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84% (40)
Prestige Cumbria Boot

Prestige Cumbria Boot

£54.95

Typical High Street Price: £85.75

Save £30.80

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% (53)
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% (44)
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% (42)
Prestige Belgravia Shoe

Prestige Belgravia Shoe

£54.95

Typical High Street Price: £85.75

Save £30.80

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

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92% (60)
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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92% (78)
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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82% (31)
Prestige Chukka Boot - Rubber Sole

Prestige Chukka Boot - Rubber Sole

£54.95

Typical High Street Price: £85.75

Save £30.80

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% (34)
Prestige Chukka Boot - Rubber Sole

Prestige Chukka Boot - Rubber Sole

£54.95

Typical High Street Price: £85.75

Save £30.80

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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94% (23)
Prestige Balham Boot - Brown

NEW

Prestige Balham Boot - Brown

£54.95

Typical High Street Price: £85.75

Save £30.80

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

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90% (2)
Prestige Balham Boot - Black

NEW

Prestige Balham Boot - Black

£54.95

Typical High Street Price: £85.75

Save £30.80

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

£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% (153)
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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92% (70)

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.