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Most Popular

  1. Classic Oxford Shoe £35.00

  2. Classic Cheltenham Brogue £35.00

  3. Classic Penny Loafer Shoe - Black £35.00

  4. Prestige Chelsea Boot £45.00

  5. Prestige Oxford Shoe - Rubber Sole £45.00

  6. Prestige Semi-Brogue £45.00

  7. Classic Semi-Brogue £35.00

  8. Classic Penny Loafer £35.00

  9. Tweed Jacket - Chester £39.00

  10. Classic City Shoe £35.00

Mens Classic Leather ShoesFROM £14.99

Classic Slip-On Boat Shoe More Info

Classic Slip-On Boat Shoe

£35.00 WAS £44.95

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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8 reviews

Classic Lace-Up Boat Shoe More Info

Classic Lace-Up Boat Shoe

£35.00 WAS £44.95

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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4 reviews

Classic Oxford Shoe More Info

Classic Oxford Shoe

£35.00 WAS £44.95

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

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31 reviews

Classic Oxford Shoe More Info

Classic Oxford Shoe

£35.00 WAS £44.95

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

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16 reviews

Classic Semi-Brogue More Info

Classic Semi-Brogue

£35.00 WAS £44.95

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

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26 reviews

Classic Quarter-Brogue More Info

Classic Quarter-Brogue

£35.00 WAS £44.95

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

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21 reviews

Classic Sandhurst Shoe More Info

Classic Sandhurst Shoe

£35.00 WAS £44.95

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

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20 reviews

Classic Deck Shoe More Info

Classic Deck Shoe

£35.00 WAS £44.95

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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39 reviews

Classic Deck Shoe More Info

Classic Deck Shoe

£35.00 WAS £44.95

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

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30 reviews

Classic Derby Shoe More Info

Classic Derby Shoe

£35.00 WAS £44.95

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

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52 reviews

Classic Derby Shoe More Info

Classic Derby Shoe

£35.00 WAS £44.95

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

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60 reviews

Classic Royal Brogue More Info

Classic Royal Brogue

£35.00 WAS £44.95

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

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65 reviews

Classic Durham Shoe More Info

Classic Durham Shoe

£35.00 WAS £44.95

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

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50 reviews

Classic Penny Loafer More Info

Classic Penny Loafer

£35.00 WAS £44.95

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

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67 reviews

Classic Claridge Shoe More Info

Classic Claridge Shoe

£35.00 WAS £44.95

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

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47 reviews

Classic Deck Shoe More Info

Classic Deck Shoe

£35.00 WAS £44.95

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

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98 reviews

Classic Deck Shoe More Info

Classic Deck Shoe

£35.00 WAS £44.95

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

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40 reviews

Classic Deck Shoe More Info

Classic Deck Shoe

£35.00 WAS £44.95

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

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no reviews

Classic Sandhurst Shoe More Info

Classic Sandhurst Shoe

£35.00 WAS £44.95

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

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49 reviews

Classic Leather Trainer More Info

Classic Leather Trainer

£35.00 WAS £44.95

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

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41 reviews

Classic Camden Shoe More Info

Classic Camden Shoe

£14.99 WAS £44.95

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

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12 reviews

Classic Sandhurst Shoe More Info

Classic Sandhurst Shoe

£35.00 WAS £44.95

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

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147 reviews

Classic Penny Loafer More Info

Classic Penny Loafer

£35.00 WAS £44.95

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

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71 reviews

Classic Semi-Brogue More Info

Classic Semi-Brogue

£35.00 WAS £44.95

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

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102 reviews

Classic Oxford Shoe More Info

Classic Oxford Shoe

£35.00 WAS £44.95

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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367 reviews

Classic Semi-Brogue More Info

Classic Semi-Brogue

£35.00 WAS £44.95

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

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54 reviews

Classic Quarter-Brogue More Info

Classic Quarter-Brogue

£35.00 WAS £44.95

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

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98 reviews

Classic Monk Shoe More Info

Classic Monk Shoe

£35.00 WAS £44.95

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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123 reviews

Classic Monk Shoe - Chestnut Brown More Info

Classic Monk Shoe - Chestnut Brown

£35.00 WAS £44.95

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

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99 reviews

Classic Penny Loafer Shoe - Black More Info

Classic Penny Loafer Shoe - Black

£35.00 WAS £44.95

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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213 reviews

Classic Penny Loafer More Info

Classic Penny Loafer

£35.00 WAS £44.95

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

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106 reviews

Classic Oxford Shoe More Info

Classic Oxford Shoe

£35.00 WAS £44.95

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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169 reviews

Classic City Shoe More Info

Classic City Shoe

£35.00 WAS £44.95

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

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142 reviews

Classic Richmond Shoe More Info

Classic Richmond Shoe

£35.00 WAS £44.95

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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45 reviews

Classic Cheltenham Brogue More Info

Classic Cheltenham Brogue

£35.00 WAS £44.95

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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266 reviews

Classic Kempton Shoe More Info

Classic Kempton Shoe

£35.00 WAS £44.95

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

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93 reviews

Classic Kempton Shoe More Info

Classic Kempton Shoe

£35.00 WAS £44.95

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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114 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.