Choose Country:

Samuel Windsor Australia
Feefo
Done

Classic Shoes

Here at Samuel Windsor, our collection of men's classic shoes features footwear made only from premium grade leather and suede. Constructed using traditional methods, our classic collection offers a comfortable shoe for every occasion – from formal men's Oxford shoes through to relaxed boat shoes for the weekend.

Read More
Refine By
Sale

Any 2 for $150

Classic Boat Shoe - Navy/Brown

Classic Boat Shoe - Navy/Brown

(130)

$120.00 $85.00 Save $35.00

Sale

Any 2 for $150

Classic Boat Shoe - Tobacco

Classic Boat Shoe - Tobacco

(45)

$120.00 $85.00 Save $35.00

Sale

Any 2 for $150

Classic Boat Shoe - Blue

Classic Boat Shoe - Blue

(43)

$120.00 $85.00 Save $35.00

Sale

Any 2 for $150

Classic Leather Driving Shoe

Classic Leather Driving Shoe

(86)

$120.00 $85.00 Save $35.00

Sale

Any 2 for $150

Classic Suede Driving Shoe

Classic Suede Driving Shoe

(110)

$120.00 $85.00 Save $35.00

Sale

Any 2 for $150

Classic Moccasin

Classic Moccasin

(119)

$120.00 $85.00 Save $35.00

Sale

Any 2 for $150

Classic Lightweight Brogue - Navy

Classic Lightweight Brogue - Navy

(43)

$120.00 $85.00 Save $35.00

Sale

Any 2 for $150

Classic Chichester Shoe - Oxblood

Classic Chichester Shoe - Oxblood

(163)

$130.00 $85.00 Save $45.00

Sale

Any 2 for $150

Classic Slip-On Boat Shoe - Navy/Brown

Classic Slip-On Boat Shoe - Navy/Brown

(431)

$120.00 $85.00 Save $35.00

Sale

Any 2 for $150

Classic Slip-On Boat Shoe - Camel

Classic Slip-On Boat Shoe - Camel

(431)

$120.00 $85.00 Save $35.00

Sale

Any 2 for $150

Classic Derby Shoe - Black Suede

Classic Derby Shoe - Black Suede

(17)

$130.00 $85.00 Save $45.00

Sale

Any 2 for $150

Classic Derby Shoe - Black

Classic Derby Shoe - Black

(57)

$130.00 $85.00 Save $45.00

Sale

Any 2 for $150

Classic Derby Shoe - Suede

Classic Derby Shoe - Suede

(11)

$130.00 $85.00 Save $45.00

Sale

Any 2 for $150

Classic Cheltenham Brogue In Suede - Mid Brown

Classic Cheltenham Brogue In Suede - Mid Brown

(70)

$120.00 $85.00 Save $35.00

Sale

Any 2 for $150

Classic Oxford Shoe - Tan

Classic Oxford Shoe - Tan

(400)

$120.00 $85.00 Save $35.00

Sale

Any 2 for $150

Classic Chichester Shoe - Black

Classic Chichester Shoe - Black

(163)

$130.00 $85.00 Save $45.00

Sale

Any 2 for $150

Classic Oxblood Cheltenham Brogue

Classic Oxblood Cheltenham Brogue

(314)

$120.00 $85.00 Save $35.00

Sale

Any 2 for $150

Classic Suede Oxford Shoe

Classic Suede Oxford Shoe

(79)

$120.00 $85.00 Save $35.00

Sale

Any 2 for $150

Classic Oxford Shoe - Oxblood

Classic Oxford Shoe - Oxblood

(364)

$120.00 $85.00 Save $35.00

Sale

Any 2 for $150

Classic Cheltenham Brogue in Suede

Classic Cheltenham Brogue in Suede

(150)

$120.00 $85.00 Save $35.00

Sale

Any 2 for $150

Classic Sandhurst Shoe

Classic Sandhurst Shoe

(1333)

$120.00 $85.00 Save $35.00

Sale

Any 2 for $150

Classic Tan Cheltenham Brogue

Classic Tan Cheltenham Brogue

(178)

$120.00 $85.00 Save $35.00

Sale

Any 2 for $150

Classic Penny Loafer - Black Suede

Classic Penny Loafer - Black Suede

(79)

$105.00 $85.00 Save $20.00

Sale

Any 2 for $150

Classic Monk Brogue - Black

Classic Monk Brogue - Black

(283)

$120.00 $85.00 Save $35.00

Sale

Any 2 for $150

Classic Slip-On Deck Shoe

Classic Slip-On Deck Shoe

(431)

$120.00 $85.00 Save $35.00

Sale

Any 2 for $150

Classic Semi-Brogue - Black

Classic Semi-Brogue - Black

(4135)

$120.00 $85.00 Save $35.00

Sale

Any 2 for $150

Classic Deck Shoe

Classic Deck Shoe

(750)

$120.00 $85.00 Save $35.00

Sale

Any 2 for $150

Classic Penny Loafer - Dark Brown Suede

Classic Penny Loafer - Dark Brown Suede

(385)

$105.00 $85.00 Save $20.00

Sale

Any 2 for $150

Classic Oxford Shoe - Black

Classic Oxford Shoe - Black

(8335)

$120.00 $85.00 Save $35.00

Sale

Any 2 for $150

Classic Penny Loafer - Brown Suede

Classic Penny Loafer - Brown Suede

(959)

$120.00 $85.00 Save $35.00

Sale

Any 2 for $150

Classic Quarter-Brogue - Black

Classic Quarter-Brogue - Black

(1786)

$120.00 $85.00 Save $35.00

Sale

Any 2 for $150

Classic Cheltenham Brogue - Black

Classic Cheltenham Brogue - Black

(3249)

$120.00 $85.00 Save $35.00

Sale

Any 2 for $150

Classic Kempton Shoe - Black

Classic Kempton Shoe - Black

(2089)

$130.00 $85.00 Save $45.00

Sale

Any 2 for $150

Classic Kempton Shoe

Classic Kempton Shoe

(2652)

$105.00 $85.00 Save $20.00

Sale

Any 2 for $150

Classic Oxford Shoe - Brown

Classic Oxford Shoe - Brown

(2526)

$120.00 $85.00 Save $35.00

Sale

Any 2 for $150

Classic Monk Shoe - Black

Classic Monk Shoe - Black

(2438)

$120.00 $85.00 Save $35.00

Sale

Any 2 for $150

Classic Monk Shoe - Brown

Classic Monk Shoe - Brown

(1667)

$120.00 $85.00 Save $35.00

Sale

Any 2 for $150

Classic Penny Loafer Shoe - Black

Classic Penny Loafer Shoe - Black

(4123)

$105.00 $85.00 Save $20.00

Sale

Any 2 for $150

Classic Penny Loafer - Brown

Classic Penny Loafer - Brown

(2126)

$120.00 $85.00 Save $35.00

Sale

Any 2 for $150

Classic Sandhurst Shoe - Black

Classic Sandhurst Shoe - Black

(370)

$120.00 $85.00 Save $35.00

Facebook Pixel RedEye Pixel