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All Men's Shoes

Discover handmade men's shoes at incredible prices, here at Samuel Windsor. Made from the finest leather and suede, our high quality men's shoes are available in a wide choice of styles and colors. Need some formal shoes? Our smart leather Oxfords take you everywhere from the office to black tie events. Something more sturdy? Check out our prestige men's boots with non-slip rubber soles for rugged, hardwearing comfort.

New

Any 2 pairs for $140

Prestige Slip-On Deck Shoe - Brown

Any 2 pairs for $140

Prestige Tasselled Loafer - Sand

Any 2 pairs for $120

Classic Boat Shoe - Blue

Any 2 pairs for $120

Classic Boat Shoe - Tobacco

Any 2 pairs for $120

Classic Boat Shoe - Navy/Brown

Any 2 pairs for $140

Prestige Lightweight Oxford - Brown

Any 2 pairs for $140

Prestige Suede Chelsea Boot - Navy

Any 2 pairs for $140

Prestige Lightweight Brogue - Navy

Any 2 pairs for $140

Prestige Lightweight Brogue - Sand

Any 2 pairs for $140

Prestige Suede Chelsea Boot - Sand

Any 2 pairs for $140

Prestige Lightweight Derby - Tan

Any 2 pairs for $140

Prestige Driving Shoe - Navy/Brown

Any 2 pairs for $120

Classic Moccasin

Classic Moccasin

(99)

$69.00

Any 2 pairs for $120

Classic Moccasin - Brown

Any 2 pairs for $120

Classic Suede Driving Shoe

Any 2 pairs for $140

Prestige Penny Loafer - Suede - Black

Any 2 pairs for $120

Classic Cheltenham Brogue In Suede - Mid Brown

Any 2 pairs for $120

Classic Chichester Shoe - Black

Any 2 pairs for $120

Classic Monk Shoe - Black

Any 2 pairs for $120

Classic Monk Shoe - Brown

Any 2 pairs for $120

Classic Penny Loafer Shoe - Black

Any 2 pairs for $120

Classic Penny Loafer - Brown

Any 2 pairs for $120

Classic Semi-Brogue

Classic Semi-Brogue

(1660)

$69.00

Any 2 pairs for $120

Classic Oxford Shoe - Brown

Any 2 pairs for $120

Classic Oxblood Cheltenham Brogue

Any 2 pairs for $120

Classic Suede Oxford Shoe

Any 2 pairs for $120

Classic Oxford Shoe - Oxblood

Any 2 pairs for $120

Classic Oxford Shoe - Mid-Brown

Any 2 pairs for $120

Classic Oxford Shoe - Tan

Any 2 pairs for $120

Classic Cheltenham Brogue in Suede

Any 2 pairs for $120

Classic Sandhurst Shoe

Classic Sandhurst Shoe

(1296)

$69.00

Any 2 pairs for $120

Classic Tan Cheltenham Brogue

Any 2 pairs for $120

Classic Penny Loafer - Black Suede

Any 2 pairs for $120

Classic Monk Brogue - Black

Any 2 pairs for $120

Classic Slip-On Boat Shoe

Any 2 pairs for $120

Classic Semi-Brogue - Black

Any 2 pairs for $120

Classic Boat Shoe

Classic Boat Shoe

(674)

$69.00

Any 2 pairs for $120

Classic Penny Loafer - Dark Brown Suede

Any 2 pairs for $120

Classic Penny Loafer - Brown Suede

Any 2 pairs for $120

Classic Oxford Shoe - Black

Any 2 pairs for $120

Classic Quarter-Brogue - Black

Any 2 pairs for $120

Classic Cheltenham Brogue - Black

Any 2 pairs for $120

Classic City Shoe - Black

Any 2 pairs for $120

Classic Kempton Shoe - Black

Any 2 pairs for $120

Classic Kempton Shoe

Classic Kempton Shoe

(2565)

$69.00

Any 2 pairs for $140

Prestige Tasselled Loafer - Black

Any 2 pairs for $140

Prestige Dress Shoe - Black

Any 2 pairs for $140

Prestige Oxford Dress Shoe - Black

Any 2 pairs for $140

Prestige Leather Lace-Up Boat Shoe

Any 2 pairs for $140

Prestige Lace-Up Boat Shoe

Any 2 pairs for $140

Prestige Boat Shoe

Prestige Boat Shoe

(218)

$79.00

Any 2 pairs for $140

Prestige Cumbria Boot

Prestige Cumbria Boot

(168)

$79.00

Any 2 pairs for $140

Prestige Tasselled Suede Loafer

Any 2 pairs for $140

Prestige Twin Monk Shoe - Oxblood

Any 2 pairs for $140

Prestige Twin Monk - Black

Any 2 pairs for $140

Prestige Slip-On Boat Shoe - Brown

Any 2 pairs for $140

Prestige Slip-On Boat Shoe - Green

Any 2 pairs for $140

Prestige Penny Loafer - Black

Any 2 pairs for $140

Prestige Semi-Brogue

Prestige Semi-Brogue

(564)

$79.00

Any 2 pairs for $140

Prestige Oxford Shoe - Black

Any 2 pairs for $140

Prestige Chelsea Boot

Prestige Chelsea Boot

(305)

$79.00

Any 2 pairs for $140

Prestige Chelsea Boot - Black

Any 2 pairs for $140

Prestige Suede Chelsea Boot

Any 2 pairs for $140

Prestige Semi-Brogue - Black

Any 2 pairs for $140

Prestige Belgravia Shoe

Mule - Black

(181)

$52.50

Mule - Brown

(94)

$52.50

Fisherman's Sandals

(103)

$55.00

Outdoor Mule - Black

(536)

$52.50

Outdoor Mule - Brown

(1075)

$52.50

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