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Most Popular

  1. Classic Oxford Shoe £35.00

  2. Prestige Chelsea Boot £45.00

  3. Classic Cheltenham Brogue £35.00

  4. Classic Penny Loafer Shoe - Black £35.00

  5. Prestige Chelsea Boot £45.00

  6. Prestige Oxford Shoe - Rubber Sole £45.00

  7. Prestige Semi-Brogue £45.00

  8. Prestige Oxford Shoe £45.00

  9. Classic Semi-Brogue £35.00

  10. Classic Penny Loafer £35.00

Mens Slip-On Leather ShoesFROM £35.00

Prestige Slip-On Boat Shoe More Info

Prestige Slip-On Boat Shoe

£45.00 WAS £59.95

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

SAVE £14.95

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6 reviews

Classic Slip-On Boat Shoe More Info

Classic Slip-On Boat Shoe

£35.00 WAS £44.95

These Classic Slip-On Boat Shoes are handmade by Samuel Windsor. These designer slip-on shoes are crafted using only the finest leathers.

SAVE £9.95

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9 reviews

Prestige Slip-On Boat Shoe More Info

Prestige Slip-On Boat Shoe

£45.00 WAS £59.95

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

SAVE £14.95

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11 reviews

Prestige Moccasin More Info

Prestige Moccasin

£45.00 WAS £59.95

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

SAVE £14.95

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no reviews

Prestige Dealer Boot - Rubber Sole More Info

Prestige Dealer Boot - Rubber Sole

£45.00 WAS £59.95

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

SAVE £14.95

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21 reviews

Prestige Dealer Boot - Rubber Sole More Info

Prestige Dealer Boot - Rubber Sole

£45.00 WAS £59.95

Prestige Dealer Boot - Tobacco, online from Samuel Windsor. Tailored quality at outstanding prices.

SAVE £14.95

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no reviews

Prestige Tasselled Loafer More Info

Prestige Tasselled Loafer

£45.00 WAS £59.95

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

SAVE £14.95

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12 reviews

Prestige Hereford Shoe More Info

Prestige Hereford Shoe

£45.00 WAS £59.95

Prestige Hereford Shoes - Navy Suede, online from Samuel Windsor. Tailored quality at outstanding prices.

SAVE £14.95

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25 reviews

Prestige Pembroke Shoe - Brown More Info

Prestige Pembroke Shoe - Brown

£45.00 WAS £59.95

Prestige Pembroke Shoe - Brown, online from Samuel Windsor. Tailored quality at outstanding prices.

SAVE £14.95

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no reviews

Prestige Penny Loafer More Info

Prestige Penny Loafer

£45.00 WAS £59.95

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

SAVE £14.95

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46 reviews

Prestige Penny Loafer More Info

Prestige Penny Loafer

£45.00 WAS £59.95

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

SAVE £14.95

More Info

37 reviews

Prestige Monk Shoe - Rubber Sole More Info

Prestige Monk Shoe - Rubber Sole

£45.00 WAS £59.95

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

SAVE £14.95

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32 reviews

Classic Penny Loafer More Info

Classic Penny Loafer

£35.00 WAS £44.95

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

SAVE £9.95

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68 reviews

Classic Claridge Shoe More Info

Classic Claridge Shoe

£35.00 WAS £44.95

Classic Claridge Shoe - Black, online from Samuel Windsor. Tailored quality at outstanding prices.

SAVE £9.95

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47 reviews

Prestige Hereford Shoe More Info

Prestige Hereford Shoe

£45.00 WAS £59.95

Prestige Hereford - Sand, online from Samuel Windsor. Tailored quality at outstanding prices.

SAVE £14.95

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no reviews

Prestige Lincoln Shoe More Info

Prestige Lincoln Shoe

£45.00 WAS £59.95

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

SAVE £14.95

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25 reviews

Prestige Tasselled Loafer More Info

Prestige Tasselled Loafer

£45.00 WAS £59.95

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

SAVE £14.95

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59 reviews

Prestige Hereford Shoe More Info

Prestige Hereford Shoe

£45.00 WAS £59.95

Prestige Hereford - Slate, online from Samuel Windsor. Tailored quality at outstanding prices.

SAVE £14.95

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no reviews

Prestige Belgravia Boot More Info

Prestige Belgravia Boot

£45.00 WAS £59.95

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

SAVE £14.95

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42 reviews

Prestige Monk Shoe - Rubber Sole More Info

Prestige Monk Shoe - Rubber Sole

£45.00 WAS £59.95

Prestige Monk Shoe - Brown - Rubber Sole, online from Samuel Windsor. Tailored quality at outstanding prices.

SAVE £14.95

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26 reviews

Prestige Tasselled Loafer More Info

Prestige Tasselled Loafer

£45.00 WAS £59.95

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

SAVE £14.95

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48 reviews

Classic Penny Loafer More Info

Classic Penny Loafer

£35.00 WAS £44.95

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

SAVE £9.95

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74 reviews

Classic Monk Shoe More Info

Classic Monk Shoe

£35.00 WAS £44.95

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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124 reviews

Classic Monk Shoe - Chestnut Brown More Info

Classic Monk Shoe - Chestnut Brown

£35.00 WAS £44.95

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

SAVE £9.95

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99 reviews

Classic Penny Loafer Shoe - Black More Info

Classic Penny Loafer Shoe - Black

£35.00 WAS £44.95

These black Penny Loafer men's leather shoes from Samuel Windsor are classic formal shoes combined with supple, easy slip-on access.

SAVE £9.95

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219 reviews

Classic Penny Loafer More Info

Classic Penny Loafer

£35.00 WAS £44.95

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

SAVE £9.95

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108 reviews

Classic Kempton Shoe More Info

Classic Kempton Shoe

£35.00 WAS £44.95

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

SAVE £9.95

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97 reviews

Classic Kempton Shoe More Info

Classic Kempton Shoe

£35.00 WAS £44.95

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.

SAVE £9.95

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116 reviews

These handmade leather slip-on shoes are available to order in sizes 5, 6, 6.5, 7, 7.5, 8, 8.5, 9, 9.5, 10, 10.5, 11, 12, 13, and 14. This range includes tasselled loafers, driving shoes, and moccasins. Why not order a pair with our mens jumbo cord trousers and a long sleeve cotton twill shirt?