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Classic Semi-Brogue - Black

Classic Semi-Brogue - Black

£39.50

Typical High Street Price: £125.99

ANY 2 PAIRS FOR £75

Classic Semi-Brogues - Black, online from Samuel Windsor. Tailored quality at outstanding prices

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(3728 reviews)
Classic Oxford Shoe - Black

Classic Oxford Shoe - Black

£39.50

Typical High Street Price: £134.74

ANY 2 PAIRS FOR £75

The Samuel Windsor commitment to quality ensures these handmade Classic black Oxford shoes will prove to be the finest, most comfortable and hardest wearing men's leather shoes you will ever invest in.

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(7312 reviews)
Classic Semi-Brogue

Classic Semi-Brogue

£39.50

Typical High Street Price: £125.99

ANY 2 PAIRS FOR £75

Classic Suede Semi-Brogues - Brown Suede, online from Samuel Windsor. Tailored quality at outstanding prices.

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(1516 reviews)
Classic Quarter-Brogue - Black

Classic Quarter-Brogue - Black

£39.50

Typical High Street Price: £125.99

ANY 2 PAIRS FOR £75

Classic Plain Toe Cap Quarter Brogue - Black, online from Samuel Windsor. Tailored quality at outstanding prices.

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(1605 reviews)
Classic Monk Shoe - Black

Classic Monk Shoe - Black

£39.50

Typical High Street Price: £124.33

ANY 2 PAIRS FOR £75

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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(2091 reviews)
Classic Monk Shoe

Classic Monk Shoe

£39.50

Typical High Street Price: £124.33

ANY 2 PAIRS FOR £75

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

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(1426 reviews)
Classic Sandhurst Shoe

Classic Sandhurst Shoe

£39.50

Typical High Street Price: £125.99

ANY 2 PAIRS FOR £75

Classic Sandhurst Shoe - Tan, online from Samuel Windsor. Tailored quality at outstanding prices.

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(1195 reviews)
Classic Penny Loafer

Classic Penny Loafer

£39.50

Typical High Street Price: £124.33

ANY 2 PAIRS FOR £75

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

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(325 reviews)
Classic Deck Shoe

Classic Deck Shoe

£39.50

Typical High Street Price: £94.75

ANY 2 PAIRS FOR £75

Classic Deck Shoe - Brown, online from Samuel Windsor. Tailored quality at outstanding prices.

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(607 reviews)
Classic Oxford Shoe

Classic Oxford Shoe

£39.50

Typical High Street Price: £134.74

ANY 2 PAIRS FOR £75

Classic Oxford Shoes - Tan, online from Samuel Windsor. Tailored quality at outstanding prices.

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(309 reviews)
Classic Slip-On Deck Shoe

Classic Slip-On Deck Shoe

£39.50

Typical High Street Price: £94.75

ANY 2 PAIRS FOR £75

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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(353 reviews)
Classic Oxford Shoe

Classic Oxford Shoe

£39.50

Typical High Street Price: £134.74

ANY 2 PAIRS FOR £75

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

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(141 reviews)
Classic Monk Brogue - Black

Classic Monk Brogue - Black

£39.50

Typical High Street Price: £124.33

ANY 2 PAIRS FOR £75

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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(182 reviews)
Classic Cheltenham Brogue in Suede

Classic Cheltenham Brogue in Suede

£39.50

Typical High Street Price: £125.99

ANY 2 PAIRS FOR £75

Buy classic suede brogues in dark brown from Samuel Windsor. Our handmade suede brogues offer a casual variation on this popular brogue design.

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(87 reviews)
Classic Cheltenham Brogue

Classic Cheltenham Brogue

£39.50

Typical High Street Price: £125.99

ANY 2 PAIRS FOR £75

Buy classic leather brogues. Our handmade tan leather brogues are stylish and comfortable, treading the line perfectly between smart and casual.

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(103 reviews)
Classic Oxford Shoe - Oxblood

Classic Oxford Shoe - Oxblood

£39.50

Typical High Street Price: £134.74

ANY 2 PAIRS FOR £75

Classic Oxford Shoes, online from Samuel Windsor. Tailored quality at outstanding prices.

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(133 reviews)
Classic Monk Shoe

Classic Monk Shoe

£28.95

Typical High Street Price: £124.33

Save £95.38

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

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(23 reviews)
Classic Penny Loafer

Classic Penny Loafer

£39.50

Typical High Street Price: £124.33

ANY 2 PAIRS FOR £75

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(28 reviews)
Classic Cheltenham Brogue

Classic Cheltenham Brogue

£39.50

Typical High Street Price: £125.99

ANY 2 PAIRS FOR £75

Buy classic black brogues from Samuel Windsor. Our handmade brogues offer Goodyear welted construction for long lasting quality. Visit now for great offers.

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(114 reviews)
Classic Suede Oxford Shoe

Classic Suede Oxford Shoe

£39.50

Typical High Street Price: £134.74

ANY 2 PAIRS FOR £75

Classic Suede Oxford Shoes in black from Samuel Windsor. Visit now for outstanding quality and fantastic offers.

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(44 reviews)
Classic Deck Shoe - Tobacco

Classic Deck Shoe - Tobacco

£26.50

Typical High Street Price: £94.75

Save £68.25

Classic Deck Shoe from Samuel Windsor online. Visit us today for discount prices on top quality mens shoes and clothing.

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(19 reviews)
Classic Deck Shoe - Blue

Classic Deck Shoe - Blue

£26.50

Typical High Street Price: £94.75

Save £68.25

Classic Deck Shoe in blue from Samuel Windsor online. Visit us today for discount prices on top quality mens shoes and clothing.

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(17 reviews)
Classic Deck Shoe - Navy/Brown

Classic Deck Shoe - Navy/Brown

£39.50

Typical High Street Price: £94.75

ANY 2 PAIRS FOR £75

Classic Deck Shoe in navy and brown from Samuel Windsor online. Visit us today for discount prices on top quality mens shoes and clothing.

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(37 reviews)
Classic Cheltenham Brogue In Suede - Mid Brown

NEW

Classic Cheltenham Brogue In Suede - Mid Brown

£39.50

Typical High Street Price: £125.99

ANY 2 PAIRS FOR £75

Buy classic suede brogues in light brown from Samuel Windsor. Our handmade suede brogues offer a casual variation on this popular brogue design.

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(3 reviews)
Classic Chichester Shoe - Black

NEW

Classic Chichester Shoe - Black

£39.50

Typical High Street Price: £134.74

ANY 2 PAIRS FOR £75

Made using time honoured shoemaking techniques, these handmade five-eyelet Classic Oxford shoes are a traditional Oxford with a modern twist.

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(5 reviews)
Classic Penny Loafer Shoe - Black

Classic Penny Loafer Shoe - Black

£39.50

Typical High Street Price: £124.33

ANY 2 PAIRS FOR £75

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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(3682 reviews)
Classic Penny Loafer

Classic Penny Loafer

£39.50

Typical High Street Price: £124.33

ANY 2 PAIRS FOR £75

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

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(1901 reviews)
Classic Oxford Shoe

Classic Oxford Shoe

£39.50

Typical High Street Price: £134.74

ANY 2 PAIRS FOR £75

Crafted using time honoured shoe making techniques, these Samuel Windsor Classic Oxford Shoes in chestnut brown are classic formal shoes or office shoes.

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(2209 reviews)
Classic City Shoe - Black

Classic City Shoe - Black

£39.50

Typical High Street Price: £129.98

ANY 2 PAIRS FOR £75

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

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(2672 reviews)
Classic Cheltenham Brogue - Black

Classic Cheltenham Brogue - Black

£39.50

Typical High Street Price: £125.99

ANY 2 PAIRS FOR £75

Buy classic black brogues. A staple shoe for the modern man, our handmade classic cheltenham brogues are the perfect shoe for formal and casual occasions.

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(2789 reviews)
Classic Kempton Shoe - Black

Classic Kempton Shoe - Black

£39.50

Typical High Street Price: £124.33

ANY 2 PAIRS FOR £75

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

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(1823 reviews)
Classic Kempton Shoe

Classic Kempton Shoe

£39.50

Typical High Street Price: £124.33

ANY 2 PAIRS FOR £75

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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(2266 reviews)
Classic Penny Loafer

Classic Penny Loafer

£39.50

Typical High Street Price: £124.33

ANY 2 PAIRS FOR £75

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

More Info
(872 reviews)

Our classic shoes collection features both formal and casual designs. Samuel Windsor's traditional shoe styles include classic tan Sandhurst shoes, formal chestnut brown Oxfords, brown suede penny loafers and casual blue deck shoes. Order your classic leather and suede shoes today. Available in UK sizes 5 to 14.