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117,707

Independent customer reviews

Most Popular

  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 Kempton Shoe
    £37.50

  6. Prestige Gibson Shoe
    £26.95

  7. Classic Monk Shoe
    £37.50

  8. Prestige Oxford Shoe
    £49.95

  9. Outdoor Mule
    £32.50

  10. Classic Semi-Brogue
    £37.50

Classic Semi-Brogue - Black

Classic Semi-Brogue - Black

£37.50

Typical High Street Price: £130.75

ANY 2 FOR £70

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

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(3644 reviews)
Classic Oxford Shoe - Black

Classic Oxford Shoe - Black

£37.50

Typical High Street Price: £130.75

ANY 2 FOR £70

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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(6984 reviews)
Classic Semi-Brogue

Classic Semi-Brogue

£37.50

Typical High Street Price: £130.75

ANY 2 FOR £70

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

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(1471 reviews)
Classic Quarter-Brogue - Black

Classic Quarter-Brogue - Black

£37.50

Typical High Street Price: £130.75

ANY 2 FOR £70

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

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(1545 reviews)
Classic Monk Shoe - Black

Classic Monk Shoe - Black

£37.50

Typical High Street Price: £132.67

ANY 2 FOR £70

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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(2016 reviews)
Classic Monk Shoe

Classic Monk Shoe

£37.50

Typical High Street Price: £132.67

ANY 2 FOR £70

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

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(1367 reviews)
Classic Sandhurst Shoe

Classic Sandhurst Shoe

£37.50

Typical High Street Price: £130.75

ANY 2 FOR £70

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

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(57 reviews)
Classic Sandhurst Shoe - Black

Classic Sandhurst Shoe - Black

£37.50

Typical High Street Price: £130.75

ANY 2 FOR £70

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

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(288 reviews)
Classic Penny Loafer

Classic Penny Loafer

£37.50

Typical High Street Price: £132.67

ANY 2 FOR £70

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

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(291 reviews)
Classic Deck Shoe

Classic Deck Shoe

£37.50

Typical High Street Price: £88.50

ANY 2 FOR £70

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

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(554 reviews)
Classic Deck Shoe

SALE

Classic Deck Shoe

£23.50

Typical High Street Price: £88.50

Save £65.00

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

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(40 reviews)
Classic Derby Shoe

SALE

Classic Derby Shoe

£23.50

Typical High Street Price: £128.00

Save £104.50

Classic Derby Shoe - Blue, online from Samuel Windsor. Tailored quality at outstanding prices.

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(297 reviews)
Classic Derby Shoe

SALE

Classic Derby Shoe

£23.50

Typical High Street Price: £128.00

Save £104.50

Classic Derby Shoe - Tobacco, online from Samuel Windsor. Tailored quality at outstanding prices.

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(236 reviews)
Classic Oxford Shoe

Classic Oxford Shoe

£37.50

Typical High Street Price: £130.75

ANY 2 FOR £70

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

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(263 reviews)
Classic Slip-On Deck Shoe

Classic Slip-On Deck Shoe

£37.50

Typical High Street Price: £88.50

ANY 2 FOR £70

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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(311 reviews)
Classic Lace-Up Deck Shoe

SALE

Classic Lace-Up Deck Shoe

£23.50

Typical High Street Price: £88.50

Save £65.00

Our Classic Lace-Up Boat Shoes are handmade by Samuel Windsor. These designer lace-up shoes are crafted using only the finest leathers.

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(128 reviews)
Classic Oxford Shoe

Classic Oxford Shoe

£37.50

Typical High Street Price: £130.75

ANY 2 FOR £70

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

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(115 reviews)
Classic Driving Shoe

SALE

Classic Driving Shoe

£23.50

Typical High Street Price: £69.38

Save £45.88

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

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(48 reviews)
Classic Moccasin

SALE

Classic Moccasin

£23.95

Typical High Street Price: £69.38

Save £45.43

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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(53 reviews)
Classic Deck Shoe

SALE

Classic Deck Shoe

£23.50

Typical High Street Price: £88.50

Save £65.00

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

More Info
(41 reviews)
Classic Durham Shoe - Black

Classic Durham Shoe - Black

£37.50

Typical High Street Price: £130.75

ANY 2 FOR £70

Classic Durham Shoe, online from Samuel Windsor. Tailored quality at outstanding prices.

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(67 reviews)
Classic Monk Brogue - Black

Classic Monk Brogue - Black

£37.50

Typical High Street Price: £132.67

ANY 2 FOR £70

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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(101 reviews)
Classic Cheltenham Brogue

Classic Cheltenham Brogue

£37.50

Typical High Street Price: £130.75

ANY 2 FOR £70

Buy classic suede brogues from Samuel Windsor. Our handmade suede brogues offer a casual variation of this classic brogue design.

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(58 reviews)
Classic Cheltenham Brogue

Classic Cheltenham Brogue

£37.50

Typical High Street Price: £130.75

ANY 2 FOR £70

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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(64 reviews)
Classic Monk Shoe

NEW

Classic Monk Shoe

£37.50

Typical High Street Price: £132.67

ANY 2 FOR £70

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

More Info
(1 reviews)
Classic Penny Loafer Shoe - Black

Classic Penny Loafer Shoe - Black

£37.50

Typical High Street Price: £132.67

ANY 2 FOR £70

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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(3564 reviews)
Classic Penny Loafer

Classic Penny Loafer

£37.50

Typical High Street Price: £132.67

ANY 2 FOR £70

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

More Info
(1845 reviews)
Classic Oxford Shoe

Classic Oxford Shoe

£37.50

Typical High Street Price: £130.75

ANY 2 FOR £70

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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(2113 reviews)
Classic City Shoe - Black

Classic City Shoe - Black

£37.50

Typical High Street Price: £128.00

ANY 2 FOR £70

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

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(2633 reviews)
Classic Cheltenham Brogue - Black

Classic Cheltenham Brogue - Black

£37.50

Typical High Street Price: £130.75

ANY 2 FOR £70

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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(2644 reviews)
Classic Kempton Shoe - Black

Classic Kempton Shoe - Black

£37.50

Typical High Street Price: £132.67

ANY 2 FOR £70

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

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(1745 reviews)
Classic Kempton Shoe

Classic Kempton Shoe

£37.50

Typical High Street Price: £132.67

ANY 2 FOR £70

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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(2191 reviews)
Classic Penny Loafer

Classic Penny Loafer

£37.50

Typical High Street Price: £132.67

ANY 2 FOR £70

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

More Info
(833 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.