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Classic Monk Shoe - Black

Classic Monk Shoe - Black

£45.00

Typical High Street Price: £137.67

ANY 2 PAIRS FOR £80

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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(2080 reviews)
Classic Monk Shoe

Classic Monk Shoe

£45.00

Typical High Street Price: £137.67

ANY 2 PAIRS FOR £80

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

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(1410 reviews)
Prestige Tasselled Loafer - Black

Prestige Tasselled Loafer - Black

£49.95

Typical High Street Price: £124.33

ANY 2 PAIRS FOR £95

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

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(528 reviews)
Prestige Tasselled Suede Loafer

Prestige Tasselled Suede Loafer

£49.95

Typical High Street Price: £124.33

ANY 2 PAIRS FOR £95

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

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(257 reviews)
Classic Penny Loafer

Classic Penny Loafer

£45.00

Typical High Street Price: £124.33

ANY 2 PAIRS FOR £80

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

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(315 reviews)
Prestige Penny Loafer - Black

Prestige Penny Loafer - Black

£49.95

Typical High Street Price: £124.33

ANY 2 PAIRS FOR £95

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

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(250 reviews)
Prestige Penny Loafer

Prestige Penny Loafer

£49.95

Typical High Street Price: £124.33

ANY 2 PAIRS FOR £95

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

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(203 reviews)
Prestige Slip-On Deck Shoe

Prestige Slip-On Deck Shoe

£49.95

Typical High Street Price: £116.00

ANY 2 PAIRS FOR £95

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

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(267 reviews)
Classic Slip-On Deck Shoe

Classic Slip-On Deck Shoe

£45.00

Typical High Street Price: £87.88

ANY 2 PAIRS FOR £80

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

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(341 reviews)
Prestige Slip-On Deck Shoe

Prestige Slip-On Deck Shoe

£49.95

Typical High Street Price: £116.00

ANY 2 PAIRS FOR £95

Our Prestige Slip-on Boat Shoes with contrasting colours is the epitome of casual sophistication. Visit us now for great offers on leather deck shoes.

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(289 reviews)
Classic Driving Shoe

Classic Driving Shoe

£45.00

Typical High Street Price: £80.50

ANY 2 PAIRS FOR £80

Classic Driving Shoe are comfortable to wear which is perfect for the summer.

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(72 reviews)
Classic Moccasin

Classic Moccasin

£45.00

Typical High Street Price: £80.50

ANY 2 PAIRS FOR £80

Made from the finest, soft Italian leather, our Classic moccasins are carefully hand stitched, creating a wonderfully comfortable and durable casual shoe.

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(74 reviews)
Prestige Twin Monk - Black

Prestige Twin Monk - Black

£49.95

Typical High Street Price: £137.67

ANY 2 PAIRS FOR £95

Prestige Twin Monk, online from Samuel Windsor. Tailored quality at outstanding prices.

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(103 reviews)
Classic Monk Brogue - Black

Classic Monk Brogue - Black

£45.00

Typical High Street Price: £137.67

ANY 2 PAIRS FOR £80

These monk brogue shoes have been producted using the finest Italian leathers and using a goodyear welted construction which offers and unbeatable combination of durability and comfort and an exceptional price.

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(166 reviews)
Prestige Penny Loafer Suede - Navy

Prestige Penny Loafer Suede - Navy

£59.50

Typical High Street Price: £124.33

ANY 2 FOR £110

Classic Black Suede Penny loafers from Samuel Windsor. Visit now for outstanding offers.

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(38 reviews)
Prestige Penny Loafer Suede - Brown

Prestige Penny Loafer Suede - Brown

£59.50

Typical High Street Price: £124.33

ANY 2 FOR £110

Classic Brown Suede Penny loafers from Samuel Windsor. Visit now for outstanding offers.

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(32 reviews)
Classic Monk Shoe

Classic Monk Shoe

£45.00

Typical High Street Price: £137.67

ANY 2 PAIRS FOR £80

These handmade Monk Shoes are another traditional classic from Samuel Windsor, painstakingly constructed from over 50 natural components.

More Info
(19 reviews)
Classic Penny Loafer

Classic Penny Loafer

£45.00

Typical High Street Price: £124.33

ANY 2 PAIRS FOR £80

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(23 reviews)
Prestige Twin Monk Shoe - Oxblood

Prestige Twin Monk Shoe - Oxblood

£49.95

Typical High Street Price: £137.67

ANY 2 PAIRS FOR £95

Suave and sophisticated; the wonderfully hand crafted Prestige Oxblood Twin Monk.

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(30 reviews)
Classic Driving Shoe

NEW

Classic Driving Shoe

£45.00

Typical High Street Price: £80.50

ANY 2 PAIRS FOR £80

Classic Driving Shoe are comfortable to wear which is perfect for the summer.

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(6 reviews)
Classic Moccasin - Brown

NEW

Classic Moccasin - Brown

£45.00

Typical High Street Price: £80.50

ANY 2 PAIRS FOR £80

Made from the finest, soft Italian leather, our Classic moccasins are carefully hand stitched, creating a wonderfully comfortable and durable casual shoe.

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(2 reviews)
Prestige Penny Loafer - Suede - Black

NEW

Prestige Penny Loafer - Suede - Black

£59.50

Typical High Street Price: £124.33

ANY 2 FOR £110

Classic Black Suede Penny loafers from Samuel Windsor. Visit now for outstanding offers.

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(1 reviews)
Prestige Tasselled Loafer - Sand

NEW

Prestige Tasselled Loafer - Sand

£49.95

Typical High Street Price: £124.33

ANY 2 PAIRS FOR £95

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

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(2 reviews)
Prestige Driving Shoe - Navy/Brown

NEW

Prestige Driving Shoe - Navy/Brown

£49.95

Typical High Street Price: £116.00

ANY 2 PAIRS FOR £95

Made from the finest, super-soft Italian Nubuck leather, our two-tone Prestige driving shoes are carefully handmade using genuine moccasin stitching

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(2 reviews)
Classic Penny Loafer Shoe - Black

Classic Penny Loafer Shoe - Black

£45.00

Typical High Street Price: £124.33

ANY 2 PAIRS FOR £80

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

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(3659 reviews)
Classic Penny Loafer

Classic Penny Loafer

£45.00

Typical High Street Price: £124.33

ANY 2 PAIRS FOR £80

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

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(1891 reviews)
Classic Kempton Shoe - Black

Classic Kempton Shoe - Black

£45.00

Typical High Street Price: £124.33

ANY 2 PAIRS FOR £80

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

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(1804 reviews)
Classic Kempton Shoe

Classic Kempton Shoe

£45.00

Typical High Street Price: £124.33

ANY 2 PAIRS FOR £80

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.

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(2239 reviews)
Classic Penny Loafer

Classic Penny Loafer

£45.00

Typical High Street Price: £124.33

ANY 2 PAIRS FOR £80

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

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(866 reviews)

These luxury leather slip-on shoes are available to order in sizes from 5 to 14. Find a pair for every occasion, there's tasselled loafers for going out in town and leather slippers for lounging about at home. Need shoes for more formal occasions? Don't miss our Oxford shoes, Brogues and Derbys plus many more in the Samuel Windsor lace ups collection.