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Classic Monk Shoe - Black

Classic Monk Shoe - Black

$69.00
Was $135.00

Buy 2 pairs for $130

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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(2099 reviews)
Classic Monk Shoe

Classic Monk Shoe

$69.00
Was $135.00

Buy 2 pairs for $130

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

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(1429 reviews)
Prestige Tasselled Loafer - Black

Prestige Tasselled Loafer - Black

$75.00
Was $149.00

Save $74.00

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

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(533 reviews)
Prestige Tasselled Suede Loafer

Prestige Tasselled Suede Loafer

$75.00
Was $149.00

Save $74.00

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

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(265 reviews)
Classic Penny Loafer

Classic Penny Loafer

$69.00
Was $135.00

Buy 2 pairs for $130

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

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(327 reviews)
Prestige Penny Loafer - Black

Prestige Penny Loafer - Black

$75.00
Was $149.00

Save $74.00

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

More Info
(256 reviews)
Prestige Penny Loafer

Prestige Penny Loafer

$75.00
Was $149.00

Save $74.00

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

More Info
(209 reviews)
Prestige Slip-On Deck Shoe

Prestige Slip-On boat Shoe

$75.00
Was $149.00

Save $74.00

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

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(297 reviews)
Classic Slip-On Deck Shoe

Classic Slip-On boat Shoe

$69.00
Was $135.00

Buy 2 pairs for $130

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

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(354 reviews)
Prestige Slip-On Deck Shoe

Prestige Slip-On boat Shoe

$75.00
Was $149.00

Save $74.00

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

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(297 reviews)
Classic Driving Shoe

Classic Driving Shoe

$59.00
Was $135.00

Save $76.00

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

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(85 reviews)
Classic Moccasin

Classic Moccasin

$59.00
Was $135.00

Save $76.00

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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(86 reviews)
Prestige Twin Monk - Black

Prestige Twin Monk - Black

$75.00
Was $149.00

Save $74.00

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

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(108 reviews)
Classic Monk Brogue - Black

Classic Monk Brogue - Black

$69.00
Was $135.00

Buy 2 pairs for $130

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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(184 reviews)
Prestige Penny Loafer Suede - Navy

Prestige Penny Loafer Suede - Navy

$79.00
Was $159.00

Save $80.00

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

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(50 reviews)
Prestige Penny Loafer Suede - Brown

Prestige Penny Loafer Suede - Brown

$79.00
Was $159.00

Save $80.00

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

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(35 reviews)
Classic Monk Shoe

Classic Monk Shoe

$59.00
Was $135.00

Save $76.00

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

More Info
(23 reviews)
Classic Penny Loafer

Classic Penny Loafer

$69.00
Was $135.00

Buy 2 pairs for $130

More Info
(28 reviews)
Prestige Twin Monk Shoe - Oxblood

Prestige Twin Monk Shoe - Oxblood

$75.00
Was $149.00

Save $74.00

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

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(36 reviews)
Classic Leather Driving Shoe

Classic Leather Driving Shoe

$59.00
Was $135.00

Save $76.00

Classic leather driving shoes are the perfect shoes for your travels. Visit now for great offers at Samuel Windsor.

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(34 reviews)
Classic Moccasin - Brown

Classic Moccasin - Brown

$59.00
Was $135.00

Save $76.00

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

More Info
(17 reviews)
Prestige Penny Loafer - Suede - Black

Prestige Penny Loafer - Suede - Black

$79.00
Was $159.00

Save $80.00

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

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(8 reviews)
Prestige Tasselled Loafer - Sand

Prestige Tasselled Loafer - Sand

$69.00
Was $149.00

Save $80.00

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

More Info
(11 reviews)
Prestige Driving Shoe - Navy/Brown

Prestige Driving Shoe - Navy/Brown

$69.00
Was $149.00

Save $80.00

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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(15 reviews)
Classic Penny Loafer Shoe - Black

Classic Penny Loafer Shoe - Black

$69.00
Was $135.00

Buy 2 pairs for $130

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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(3690 reviews)
Classic Penny Loafer

Classic Penny Loafer

$69.00
Was $135.00

Buy 2 pairs for $130

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

More Info
(1904 reviews)
Classic Kempton Shoe - Black

Classic Kempton Shoe - Black

$69.00
Was $135.00

Buy 2 pairs for $130

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

More Info
(1827 reviews)
Classic Kempton Shoe

Classic Kempton Shoe

$69.00
Was $135.00

Buy 2 pairs for $130

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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(2267 reviews)
Classic Penny Loafer

Classic Penny Loafer

$69.00
Was $135.00

Buy 2 pairs for $130

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

More Info
(873 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.