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Mens Classic Leather ShoesFROM £14.99

Classic Slip-On Boat Shoe - Light Brown More Info

Classic Slip-On Boat Shoe - Light Brown

£44.95 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.

BUY ANY 2 PAIRS FOR £75

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no reviews

Classic Lace-Up Boat Shoe - Ochre More Info

Classic Lace-Up Boat Shoe - Ochre

£44.95 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.

BUY ANY 2 PAIRS FOR £75

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no reviews

Classic Oxford Shoe - Tan More Info

Classic Oxford Shoe - Tan

£44.95 was £100.00

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

BUY ANY 2 PAIRS FOR £75

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24 reviews

Classic Oxford Shoe - Brown More Info

Classic Oxford Shoe - Brown

£44.95 was £100.00

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

BUY ANY 2 PAIRS FOR £75

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11 reviews

Classic Semi-Brogue - Brown More Info

Classic Semi-Brogue - Brown

£44.95 was £100.00

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

BUY ANY 2 PAIRS FOR £75

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17 reviews

Classic Quarter-Brogue - Brown More Info

Classic Quarter-Brogue - Brown

£44.95 was £100.00

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

BUY ANY 2 PAIRS FOR £75

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11 reviews

Classic Sandhurst Shoe - Brown More Info

Classic Sandhurst Shoe - Brown

£44.95 was £100.00

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

BUY ANY 2 PAIRS FOR £75

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16 reviews

Classic Deck Shoe - Navy More Info

Classic Deck Shoe - Navy

£44.95 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.

BUY ANY 2 PAIRS FOR £75

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33 reviews

Classic Deck Shoe - Nubuck More Info

Classic Deck Shoe - Nubuck

£44.95 was £100.00

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

BUY ANY 2 PAIRS FOR £75

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27 reviews

Classic Derby Shoe - Blue More Info

Classic Derby Shoe - Blue

£44.95 was £100.00

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

BUY ANY 2 PAIRS FOR £75

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66 reviews

Classic Derby Shoe - Tobacco More Info

Classic Derby Shoe - Tobacco

£44.95 was £100.00

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

BUY ANY 2 PAIRS FOR £75

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68 reviews

Classic Royal Brogue - Brown Suede More Info

Classic Royal Brogue - Brown Suede

£44.95 was £100.00

Classic Royal Brogue - Brown Suede, online from Samuel Windsor. Tailored quality at outstanding prices.

BUY ANY 2 PAIRS FOR £75

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72 reviews

Classic Durham Shoe - Tan More Info

Classic Durham Shoe - Tan

£44.95 was £100.00

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

BUY ANY 2 PAIRS FOR £75

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54 reviews

Classic Penny Loafer - Dark Brown Suede More Info

Classic Penny Loafer - Dark Brown Suede

£44.95 was £100.00

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

BUY ANY 2 PAIRS FOR £75

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64 reviews

Classic Claridge Shoe - Black More Info

Classic Claridge Shoe - Black

£44.95 was £100.00

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

BUY ANY 2 PAIRS FOR £75

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43 reviews

Classic Deck Shoe - Brown More Info

Classic Deck Shoe - Brown

£44.95 was £100.00

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

BUY ANY 2 PAIRS FOR £75

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116 reviews

Classic Deck Shoe - Blue/Brown More Info

Classic Deck Shoe - Blue/Brown

£44.95 was £100.00

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

BUY ANY 2 PAIRS FOR £75

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48 reviews

Classic Deck Shoe - Blue/Brown/White More Info

Classic Deck Shoe - Blue/Brown/White

£44.95 was £100.00

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

BUY ANY 2 PAIRS FOR £75

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21 reviews

Classic Sandhurst Shoe - Black More Info

Classic Sandhurst Shoe - Black

£44.95 was £100.00

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

BUY ANY 2 PAIRS FOR £75

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51 reviews

Classic Gibson Shoe - Black More Info

SALE

Classic Gibson Shoe - Black

£25.00 was £100.00

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

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97 reviews

Classic Leather Trainer - Brown More Info

Classic Leather Trainer - Brown

£44.95 was £100.00

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

BUY ANY 2 PAIRS FOR £75

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53 reviews

Classic Camden Shoe More Info

SALE

Classic Camden Shoe

£14.99 was £100.00

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

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12 reviews

Classic Sandhurst Shoe - Tan More Info

Classic Sandhurst Shoe - Tan

£44.95 was £100.00

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

BUY ANY 2 PAIRS FOR £75

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173 reviews

Classic Leather Trainer More Info

Classic Leather Trainer

£44.95 was £100.00

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

BUY ANY 2 PAIRS FOR £75

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31 reviews

Classic Penny Loafer - Brown Suede More Info

Classic Penny Loafer - Brown Suede

£44.95 was £100.00

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

BUY ANY 2 PAIRS FOR £75

More Info

71 reviews

Classic Semi-Brogue - Black More Info

Classic Semi-Brogue - Black

£44.95 was £100.00

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

BUY ANY 2 PAIRS FOR £75

More Info

124 reviews

Classic Oxford Shoe - Black More Info

Classic Oxford Shoe - Black

£44.95 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.

BUY ANY 2 PAIRS FOR £75

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382 reviews

Classic Semi-Brogue - Brown Suede More Info

Classic Semi-Brogue - Brown Suede

£44.95 was £100.00

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

BUY ANY 2 PAIRS FOR £75

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57 reviews

Classic Quarter-Brogue - Black More Info

Classic Quarter-Brogue - Black

£44.95 was £100.00

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

BUY ANY 2 PAIRS FOR £75

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90 reviews

Classic Monk Shoe -  Black More Info

Classic Monk Shoe - Black

£44.95 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.

BUY ANY 2 PAIRS FOR £75

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145 reviews

Classic Monk Shoe - Chestnut Brown More Info

Classic Monk Shoe - Chestnut Brown

£44.95 was £100.00

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

BUY ANY 2 PAIRS FOR £75

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114 reviews

Classic Penny Loafer Shoe - Black More Info

Classic Penny Loafer Shoe - Black

£44.95 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.

BUY ANY 2 PAIRS FOR £75

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236 reviews

Classic Penny Loafer - Chestnut Brown More Info

Classic Penny Loafer - Chestnut Brown

£44.95 was £100.00

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

BUY ANY 2 PAIRS FOR £75

More Info

109 reviews

Classic Oxford Shoe - Chestnut Brown More Info

Classic Oxford Shoe - Chestnut Brown

£44.95 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.

BUY ANY 2 PAIRS FOR £75

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194 reviews

Classic City Shoe - Black More Info

Classic City Shoe - Black

£44.95 was £100.00

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

BUY ANY 2 PAIRS FOR £75

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163 reviews

Classic Richmond Shoe - Black More Info

Classic Richmond Shoe - Black

£44.95 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.

BUY ANY 2 PAIRS FOR £75

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43 reviews

Classic Cheltenham Brogue - Black More Info

Classic Cheltenham Brogue - Black

£44.95 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.

BUY ANY 2 PAIRS FOR £75

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303 reviews

Classic Kempton Shoe - Black More Info

Classic Kempton Shoe - Black

£44.95 was £100.00

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

BUY ANY 2 PAIRS FOR £75

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105 reviews

Classic Kempton Shoe - Burgundy More Info

Classic Kempton Shoe - Burgundy

£44.95 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.

BUY ANY 2 PAIRS FOR £75

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124 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.