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Classic Shoes

If you’re after a new pair of shoes, you’ve come to the right place. Here, we’ve got a wide selection of classic shoes, suitable for any occasion. Whether you’re looking for something formal or casual, we’ve got you covered. And our products are available now at a discounted price. Order today from Mirror Reader Offers.

Classic Semi-Brogue - Black

Classic Semi-Brogue - Black

£39.95 Was £100.00

Buy 2 pairs for £75

Sale Item
90% (3716)

Classic Semi-Brogues, designed by craftsmen at Samuel Windsor, allow the foot to flex in its most natural way, ensuring maximum comfort.

Classic Oxford Shoe - Black

Classic Oxford Shoe - Black

£39.95 Was £100.00

Buy 2 pairs for £75

Sale Item
92% (7277)

Oxford Shoes have been designed using time honoured shoe making techniques. These handmade five-eyelet Men's Classic Oxford Shoes, with sleek polished quarters and a definitive cap toe, are a gentleman's classic.

Classic Semi-Brogue

Classic Semi-Brogue

£39.95 Was £100.00

Buy 2 pairs for £75

Sale Item
90% (1512)

Classic Semi-Brogue Handmade Shoes are hand crafted office shoes using open channel hand stitching.

Classic Quarter-Brogue - Black

Classic Quarter-Brogue - Black

£39.95 Was £100.00

Buy 2 pairs for £75

Sale Item
90% (1589)

Classic Plain Toe Cap Quarter Brogues boast stitched quarters, and a definitive cap toe and are suitable for all occasions.

Classic Monk Shoe - Black

Classic Monk Shoe - Black

£39.95 Was £100.00

Buy 2 pairs for £75

Sale Item
90% (2086)

Classic Monk Shoes are another traditional classic from Samuel Windsor. Intricately constructed from over 50 natural components; from the polished leather sole to the full leather lining.

Classic Monk Shoe

Classic Monk Shoe

£39.95 Was £100.00

Buy 2 pairs for £75

Sale Item
90% (1417)

Classic Monk Shoes are another traditional classic from Samuel Windsor.

Classic Sandhurst Shoe

Classic Sandhurst Shoe

£39.95 Was £100.00

Buy 2 pairs for £75

Sale Item
90% (1187)

Classic Sandhurst Shoe, are handmade by Samuel Windsor craftsmen using Goodyear Welted construction and the finest, premium grade leathers. Timeless sophisticated, and understated

Classic Penny Loafer

Classic Penny Loafer

£39.95 Was £100.00

Buy 2 pairs for £75

Sale Item
88% (321)

Classic Penny Loafers are classic formal shoes combined with supple easy slip on access.

Classic Deck Shoe

Classic Deck Shoe

£39.95 Was £100.00

Buy 2 pairs for £75

Sale Item
90% (597)

Versatile options for town or country, Classic Deck Shoes will quickly become weekend favourites.

Classic Deck Shoe

Classic Deck Shoe

£45.00 Was £100.00

Buy 2 pairs for £75

Sale Item
92% (72)

Handmade from beautiful leather, the Classic Deck Shoes are enhanced by simple stitch detailing, contrasting leather laces and completed with a man-made slip resistant sole.

Classic Oxford Shoe

Classic Oxford Shoe

£39.95 Was £100.00

Buy 2 pairs for £75

Sale Item
94% (298)

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

Classic Slip-On Boat Shoe

Classic Slip-On Boat Shoe

£39.95 Was £100.00

Buy 2 pairs for £75

Sale Item
88% (348)

Classic Slip-On Boat Shoe, timeless, sophisticated, understated yet coolly confident – they will never go out of style.

Classic Lace-Up Boat Shoe

Classic Lace-Up Boat Shoe

£45.00 Was £100.00

Buy 2 pairs for £75

Sale Item
90% (150)

Classic Lace-Up Boat Shoe, timeless, sophisticated, understated yet coolly confident – they will never go out of style.

Classic Oxford Shoe

Classic Oxford Shoe

£39.95 Was £100.00

Buy 2 pairs for £75

Sale Item
94% (137)

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

Classic Driving Shoe

Classic Driving Shoe

£39.95 Was £100.00

Buy 2 pairs for £75

Sale Item
88% (79)

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

Classic Moccasin

Classic Moccasin

£39.95 Was £100.00

Buy 2 pairs for £75

Sale Item
92% (81)

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

Classic Monk Brogue - Black

Classic Monk Brogue - Black

£39.95 Was £100.00

Buy 2 pairs for £75

Sale Item
92% (175)

Handmade using a Goodyear Welted construction, this monk brogue shoes have been produced using the finest Italian leather uppers which offer an unbeatable combination of comfort and durability representing outstanding quality at an exceptional price.

Classic Cheltenham Brogue in Suede

Classic Cheltenham Brogue in Suede

£39.95 Was £100.00

Buy 2 pairs for £75

Sale Item
92% (81)

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

Classic Cheltenham Brogue

Classic Cheltenham Brogue

£39.95 Was £100.00

Buy 2 pairs for £75

Sale Item
92% (99)

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

Classic Oxford Shoe - Oxblood

Classic Oxford Shoe - Oxblood

£39.95 Was £100.00

Buy 2 pairs for £75

Sale Item
94% (112)

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

Classic Monk Shoe

Classic Monk Shoe

£39.95 Was £100.00

Buy 2 pairs for £75

Sale Item
98% (22)

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

Classic Penny Loafer

Classic Penny Loafer

£39.95 Was £100.00

Buy 2 pairs for £75

Sale Item
92% (24)

Classic Cheltenham Brogue

Classic Cheltenham Brogue

£39.95 Was £100.00

Buy 2 pairs for £75

Sale Item
94% (89)

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

Classic Suede Oxford Shoe

Classic Suede Oxford Shoe

£39.95 Was £100.00

Buy 2 pairs for £75

Sale Item
92% (41)

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

Classic Deck Shoe - Tobacco

Classic Deck Shoe - Tobacco

£39.95 Was £100.00

Buy 2 pairs for £75

98% (8)

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

Classic Deck Shoe - Blue

Classic Deck Shoe - Blue

£39.95 Was £100.00

Buy 2 pairs for £75

92% (12)

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

Classic Driving Shoe

Classic Driving Shoe

£39.95 Was £100.00

Buy 2 pairs for £75

92% (21)

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

Classic Moccasin - Brown

Classic Moccasin - Brown

£39.95 Was £100.00

Buy 2 pairs for £75

94% (10)

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

Classic Deck Shoe - Navy/Brown

Classic Deck Shoe - Navy/Brown

£39.95 Was £100.00

Buy 2 pairs for £75

88% (32)

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

Classic Penny Loafer Shoe - Black

Classic Penny Loafer Shoe - Black

£39.95 Was £100.00

Buy 2 pairs for £75

Sale Item
88% (3668)

Classic Penny Loafer Shoe, are a handmade classic dress style combined with easy slip-on access. The Penny Loafer Shoe's accommodating leather upper has been handcrafted, raising it to the highest level of shoe quality.

Classic Penny Loafer

Classic Penny Loafer

£39.95 Was £100.00

Buy 2 pairs for £75

Sale Item
90% (1897)

Classic Penny Loafer Shoe, are a handmade classic dress style combined with easy slip-on access. The Penny Loafer Shoe's accommodating leather upper has been handcrafted, raising it to the highest level of shoe quality.

Classic Oxford Shoe

Classic Oxford Shoe

£39.95 Was £100.00

Buy 2 pairs for £75

Sale Item
92% (2198)

Using time honoured shoe making techniques, these handmade five-eyelet Classic Oxford Shoes with sleek polished quarters and a definitive cap toe, are a gentleman's classic.

Classic City Shoe - Black

Classic City Shoe - Black

£39.95 Was £100.00

Buy 2 pairs for £75

Sale Item
86% (2667)

Classic City Shoe is ideal for the work place.

Classic Cheltenham Brogue - Black

Classic Cheltenham Brogue - Black

£39.95 Was £100.00

Buy 2 pairs for £75

Sale Item
90% (2019)

Classic Cheltenham Brogues retain the elegant craftsmanship personified by hand-stitching and make a very smart and highly traditional pair of Men's Shoes.

Classic Kempton Shoe - Black

Classic Kempton Shoe - Black

£39.95 Was £100.00

Buy 2 pairs for £75

Sale Item
92% (1814)

Classic Kempton Slip-On Shoes are designed to look as good as formal shoes, office shoes or with casual wear.

Classic Kempton Shoe

Classic Kempton Shoe

£39.95 Was £100.00

Buy 2 pairs for £75

Sale Item
92% (2246)

Classic Kempton Slip-On Shoes are designed to look as good as formal shoes, office shoes or with casual wear.

Classic Penny Loafer

Classic Penny Loafer

£39.95 Was £100.00

Buy 2 pairs for £75

Sale Item
88% (870)

Classic Penny Loafer, are a handmade classic dress style combined with easy slip-on access. The Penny Loafer Shoe's accommodating leather upper has been handcrafted, raising it to the highest level of shoe quality. The Goodyear

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