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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 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 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)

Chelsea boots were made famous by The Beatles in the swinging sixties. Still on-trend today, these boots are a true statement of style. Samuel Windsor suede and leather Chelsea boots are handmade from the finest materials with Goodyear Welted construction. We stock shoes in sizes from 5 - 14, including many half sizes, so you can always find the right fit. Want more? Check out the Samuel Windsor blog, for our guide on how to wear Chelsea boots. For more quality leather and suede shoes, we also offer men's brogues, deck shoes and Oxford shoes.