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94%
98,608 Reviews

Most Popular

  1. Classic Oxford Shoe
    £35.00 Was £100.00

  2. Classic Penny Loafer Shoe
    £35.00 Was £100.00

  3. Classic Cheltenham Brogue
    £35.00 Was £100.00

  4. Churchill Suede Moccasin
    £19.99 Was £60.00

  5. Prestige Oxford
    £45.00 Was £115.00

  6. Prestige Brogue
    £27.50 Was £115.00

  7. Classic Monk Shoe
    £35.00 Was £100.00

  8. Prestige Oxford Shoe
    £45.00 Was £115.00

  9. Classic Semi-Brogue
    £35.00 Was £100.00

  10. Gentlemen's Umbrella
    £7.50 Was £50.00

Mens Classic Leather ShoesFROM £27.50

Classic Driving Shoe

NEW

Classic Driving Shoe

£35.00 Was £100.00

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

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Classic Moccasin

NEW

Classic Moccasin

£35.00 Was £100.00

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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100% (2 reviews)
Classic Deck Shoe

NEW

Classic Deck Shoe

£35.00 Was £100.00

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

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100% (2 reviews)
Nubuck Trainer - Earth Sole

NEW

Nubuck Trainer - Earth Sole

£35.00 Was £100.00

Nubuck Trainer - Earth Sole, online from Samuel Windsor. Tailored quality at outstanding prices.

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100% (3 reviews)
Casual lace-up

NEW

Casual lace-up

£35.00 Was £100.00

Casual Lace Up shoes, online from Samuel Windsor. Tailored quality at outstanding prices.

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100% (2 reviews)
Classic Semi-Brogue

Classic Semi-Brogue

£35.00 Was £100.00

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

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95% (94 reviews)
Classic Quarter-Brogue

Classic Quarter-Brogue

£35.00 Was £100.00

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

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92% (76 reviews)
Classic Sandhurst Shoe

Classic Sandhurst Shoe

£35.00 Was £100.00

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

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96% (77 reviews)
Classic Slip-On Boat Shoe

Classic Slip-On Boat Shoe

£35.00 Was £100.00

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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88% (107 reviews)
Classic Lace-Up Boat Shoe

Classic Lace-Up Boat Shoe

£35.00 Was £100.00

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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92% (37 reviews)
Classic Oxford Shoe

Classic Oxford Shoe

£35.00 Was £100.00

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

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98% (94 reviews)
Classic Oxford Shoe - Cigar

Classic Oxford Shoe - Cigar

£35.00 Was £100.00

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

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95% (148 reviews)
Classic Deck Shoe

Classic Deck Shoe

£35.00 Was £100.00

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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99% (70 reviews)
Classic Derby Shoe

SALE

Classic Derby Shoe

£27.50 Was £100.00

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

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98% (84 reviews)
Classic Derby Shoe

SALE

Classic Derby Shoe

£27.50 Was £100.00

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

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98% (59 reviews)
Classic Durham Shoe

Classic Durham Shoe

£35.00 Was £100.00

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

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89% (57 reviews)
Classic Penny Loafer

Classic Penny Loafer

£35.00 Was £100.00

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

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85% (93 reviews)
Classic Deck Shoe

Classic Deck Shoe

£35.00 Was £100.00

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

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95% (113 reviews)
Classic Deck Shoe

Classic Deck Shoe

£35.00 Was £100.00

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

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80% (152 reviews)
Classic Sandhurst Shoe - Black

Classic Sandhurst Shoe - Black

£35.00 Was £100.00

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

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93% (99 reviews)
Classic Leather Lace-Up Trainer

SALE

Classic Leather Lace-Up Trainer

£27.50 Was £100.00

Classic Leather Trainer Brown, online from Samuel Windsor. Tailored quality at outstanding prices.

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83% (48 reviews)
Classic Sandhurst Shoe

Classic Sandhurst Shoe

£35.00 Was £100.00

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

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91% (174 reviews)
Classic Penny Loafer

Classic Penny Loafer

£35.00 Was £100.00

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

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94% (93 reviews)
Classic Semi-Brogue - Black

Classic Semi-Brogue - Black

£35.00 Was £100.00

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

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96% (223 reviews)
Classic Oxford Shoe - Black

Classic Oxford Shoe - Black

£35.00 Was £100.00

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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97% (760 reviews)
Classic Semi-Brogue

Classic Semi-Brogue

£35.00 Was £100.00

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

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98% (98 reviews)
Classic Quarter-Brogue - Black

Classic Quarter-Brogue - Black

£35.00 Was £100.00

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

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99% (148 reviews)
Classic Monk Shoe - Black

Classic Monk Shoe - Black

£35.00 Was £100.00

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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95% (192 reviews)
Classic Monk Shoe

Classic Monk Shoe

£35.00 Was £100.00

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

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96% (141 reviews)
Classic Penny Loafer Shoe - Black

Classic Penny Loafer Shoe - Black

£35.00 Was £100.00

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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94% (397 reviews)
Classic Penny Loafer

Classic Penny Loafer

£35.00 Was £100.00

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

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93% (164 reviews)
Classic Oxford Shoe

Classic Oxford Shoe

£35.00 Was £100.00

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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96% (190 reviews)
Classic City Shoe - Black

Classic City Shoe - Black

£35.00 Was £100.00

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

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93% (137 reviews)
Classic Richmond Shoe - Black

Classic Richmond Shoe - Black

£35.00 Was £100.00

Great office shoes, these Samuel Windsor Richmond Classics mens black shoes are handmade, incorporating a leather lining which is both breathable and seamless.

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90% (92 reviews)
Classic Cheltenham Brogue - Black

Classic Cheltenham Brogue - Black

£35.00 Was £100.00

Cheltenham Half Brogues mens leather shoes, formal shoes or office shoes, mens brogue shoes which retain the elegant craftmanship personified by hand-stitching.

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94% (420 reviews)
Classic Kempton Shoe - Black

Classic Kempton Shoe - Black

£35.00 Was £100.00

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

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94% (174 reviews)
Classic Kempton Shoe

Classic Kempton Shoe

£35.00 Was £100.00

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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98% (248 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 in sizes 5, 6, 6.5, 7, 7.5, 8, 8.5, 9, 9.5, 10, 10.5, 11, 12, 13, and 14.

Our 'was' pricing refers to the original selling prices offered on our website www.swshoes.co.uk, and in our retail store between January 27 2016 and April 29 2016 (items sold at 'was' prices represent the lower proportion of sales).