Call us: 1844 258 0365*

Choose Country:

Samuel Windsor US
Feefo
Close

Classic Shoes

Our classic shoes for men are handstitched by master craftsmen to ensure exquisite detail and long lasting quality. We have a classic shoe for every occasion, from Oxford shoes for formal events to the casually capable boat shoe. If you're looking for timeless style, outstanding value and exceptional quality our men's classic shoe collection is unbeatable.

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
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

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

Classic Moccasin - Brown

Any 2 pairs for $140

Classic Moccasin

Classic Moccasin

(112)

$69.00

Any 2 pairs for $140

Classic Suede Driving Shoe

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

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 Sandhurst Shoe - Black

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

(1310)

$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

Any 2 pairs for $140

Classic Durham Shoe - Black
Facebook Pixel RedEye Pixel