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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 $160

Prestige Twin Monk Shoe - Tan
New

Any 2 Pairs for $160

Prestige Boat Shoe - Camel
New Prestige Fairfield Boot
New

Any 2 pairs for $140

Classic Slip-On Boat Shoe - Navy/Brown
New

Any 2 pairs for $140

Classic Slip-On Boat Shoe - Camel
New

Any 2 Pairs for $160

Prestige Boat Shoe - Navy
New

Any 2 pairs for $140

Classic Derby Shoe - Suede
New

Any 2 pairs for $140

Classic Derby Shoe - Black Suede
New

Any 2 pairs for $140

Classic Derby Shoe - Black
New

Any 2 pairs for $140

Classic Chicester Shoe - Oxblood

Any 2 pairs for $140

Prestige Lightweight Oxford - Brown

Any 2 pairs for $140

Prestige Lightweight Derby - Tan

Any 2 pairs for $140

Classic Moccasin - Brown

Any 2 pairs for $140

Classic Moccasin

Classic Moccasin

(112)

$69.00

Any 2 pairs for $140

Prestige Driving Shoe - Navy/Brown

Any 2 pairs for $140

Classic Suede Driving Shoe

Any 2 pairs for $140

Prestige Penny Loafer - Suede - Black

Any 2 pairs for $140

Prestige Tasselled Loafer - Sand

Any 2 pairs for $140

Classic Lightweight Brogue - Navy

Any 2 pairs for $140

Classic Lightweight Brogue - Sand

Any 2 pairs for $140

Classic Boat Shoe - Blue

Any 2 pairs for $140

Classic Boat Shoe - Tobacco

Any 2 pairs for $140

Classic Boat Shoe - Navy/Brown

Any 2 pairs for $140

Prestige Slip-On Boat Shoe - Brown

Any 2 pairs for $140

Classic Cheltenham Brogue In Suede - Mid Brown

Any 2 pairs for $140

Classic Chichester Shoe - Black

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

(236)

$85.00

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 Penny Loafer

Prestige Penny Loafer

(240)

$85.00

Any 2 pairs for $140

Prestige Semi-Brogue

Prestige Semi-Brogue

(578)

$85.00

Any 2 pairs for $140

Prestige Oxford Shoe - Black

Any 2 pairs for $140

Prestige Semi-Brogue - Black
Sale Outdoor Mule - Black

Outdoor Mule - Black

(33)

$40.00

Sale Outdoor Mule - Brown

Outdoor Mule - Brown

(33)

$40.00

Mule - Black

(188)

$55.00

Mule - Brown

(99)

$55.00

Fisherman's Sandals

(116)

$55.00

Any 2 pairs for $140

Classic Monk Shoe - Black

Any 2 pairs for $140

Classic Monk Shoe - Brown

Any 2 pairs for $140

Classic Penny Loafer Shoe - Black

Any 2 pairs for $140

Classic Penny Loafer - Brown

Any 2 pairs for $140

Classic Semi-Brogue

Classic Semi-Brogue

(1665)

$69.00

Any 2 pairs for $140

Classic Oxford Shoe - Brown

Any 2 pairs for $140

Classic Oxblood Cheltenham Brogue

Any 2 pairs for $140

Classic Suede Oxford Shoe

Any 2 pairs for $140

Classic Oxford Shoe - Oxblood

Any 2 pairs for $140

Classic Oxford Shoe - Mid-Brown

Any 2 pairs for $140

Classic Oxford Shoe - Tan

Any 2 pairs for $140

Classic Cheltenham Brogue in Suede

Any 2 pairs for $140

Classic Sandhurst Shoe

Classic Sandhurst Shoe

(1311)

$75.00

Any 2 pairs for $140

Classic Tan Cheltenham Brogue

Any 2 pairs for $140

Classic Penny Loafer - Black Suede

Any 2 pairs for $140

Classic Monk Brogue - Black

Any 2 pairs for $140

Classic Slip-On Boat Shoe

Any 2 pairs for $140

Classic Semi-Brogue - Black

Any 2 pairs for $140

Classic Boat Shoe

Classic Boat Shoe

(711)

$75.00

Any 2 pairs for $140

Classic Penny Loafer - Dark Brown Suede

Any 2 pairs for $140

Classic Penny Loafer - Brown Suede

Any 2 pairs for $140

Classic Oxford Shoe - Black

Any 2 pairs for $140

Classic Quarter-Brogue - Black

Any 2 pairs for $140

Classic Cheltenham Brogue - Black

Any 2 pairs for $140

Classic City Shoe - Black

Any 2 pairs for $140

Classic Kempton Shoe - Black

Any 2 pairs for $140

Classic Kempton Shoe

Classic Kempton Shoe

(2597)

$75.00

Outdoor Mule - Black

(553)

$55.00

Outdoor Mule - Brown

(1126)

$55.00

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