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All Men's Leather Shoes

Our men's leather shoes feature the finest materials, classic designs and traditional craftsmanship. Whether you're looking for a formal pair of black Oxford shoes or a relaxed pair of brown brogues, Samuel Windsor leather shoes are a sound investment.

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Sale Classic Boat Shoe - Blue

Classic Boat Shoe - Blue

(39)

Was $135.00 $45.00

Sale Classic Boat Shoe - Tobacco

Classic Boat Shoe - Tobacco

(42)

Was $135.00 $45.00

Sale

Any 2 pairs for $120

Classic Boat Shoe - Navy/Brown

Classic Boat Shoe - Navy/Brown

(111)

Was $135.00 $69.00

Sale Prestige Lightweight Derby - Tan

Prestige Lightweight Derby - Tan

(30)

Was $149.00 $50.00

Sale

Any 2 pairs for $120

Classic Derby Shoe - Suede

Classic Derby Shoe - Suede

(2)

Was $135.00 $69.00

Sale

Any 2 pairs for $120

Classic Derby Shoe - Black Suede

Classic Derby Shoe - Black Suede

(6)

Was $135.00 $69.00

Sale

Any 2 pairs for $120

Classic Derby Shoe - Black

Classic Derby Shoe - Black

(22)

Was $135.00 $69.00

Sale

Any 2 pairs for $120

Classic Chichester Shoe - Oxblood

Classic Chichester Shoe - Oxblood

(104)

Was $135.00 $69.00

Sale Prestige Derby Shoe - Tan

Prestige Derby Shoe - Tan

(7)

Was $159.00 $79.00

Sale Prestige Chelsea Boot - Rubber Sole - Black
Sale

Any 2 Pairs for $140

Prestige Twin Monk Shoe - Tan

Prestige Twin Monk Shoe - Tan

(157)

Was $149.00 $75.00

Sale Prestige Davington Brogue - Tan

Prestige Davington Brogue - Tan

(13)

Was $159.00 $79.00

Sale

Any 2 Pairs for $140

Prestige Boat Shoe - Camel

Prestige Boat Shoe - Camel

(265)

Was $149.00 $75.00

Sale Prestige Fairfield Boots - Brown

Prestige Fairfield Boots - Brown

(14)

Was $159.00 $79.00

Sale Prestige Chukka Boots - Tan

Prestige Chukka Boots - Tan

(18)

Was $189.00 $85.00

Sale Prestige Whitworth Brogue - Tan

Prestige Whitworth Brogue - Tan

(160)

Was $159.00 $79.00

Sale Prestige Davington Brogue - Black

Prestige Davington Brogue - Black

(14)

Was $159.00 $79.00

Sale Prestige Oxford Shoe - Tan

Prestige Oxford Shoe - Tan

(4)

Was $159.00 $79.00

Sale

Any 2 pairs for $120

Classic Slip-On Boat Shoe - Navy/Brown

Classic Slip-On Boat Shoe - Navy/Brown

(405)

Was $135.00 $69.00

Sale

Any 2 pairs for $120

Classic Slip-On Boat Shoe - Camel

Classic Slip-On Boat Shoe - Camel

(405)

Was $135.00 $69.00

Sale

Any 2 Pairs for $140

Prestige Boat Shoe - Navy

Prestige Boat Shoe - Navy

(265)

Was $149.00 $75.00

Sale Prestige Country Boot In Tweed

Prestige Country Boot In Tweed

(31)

Was $189.00 $90.00

Sale

Any 2 pairs for $120

Classic Cheltenham Brogue In Suede - Mid Brown
Sale

Any 2 pairs for $120

Classic Chichester Shoe - Black

Classic Chichester Shoe - Black

(104)

Was $135.00 $69.00

Sale Prestige Suede Chelsea Boot - Black

Prestige Suede Chelsea Boot - Black

(15)

Was $189.00 $85.00

Sale Prestige Suede Chelsea Boot - Brown

Prestige Suede Chelsea Boot - Brown

(25)

Was $189.00 $85.00

Sale Prestige Monk Boot - Black

Prestige Monk Boot - Black

(27)

Was $159.00 $79.00

Sale Prestige Leyton Boot - Burgundy

Prestige Leyton Boot - Burgundy

(34)

Was $159.00 $59.00

Sale Prestige Country Boot - Black

Prestige Country Boot - Black

(73)

Was $189.00 $85.00

Sale Prestige Bartlett Brogue In Tweed

Prestige Bartlett Brogue In Tweed

(35)

Was $189.00 $85.00

Sale

Any 2 pairs for $120

Classic Oxblood Cheltenham Brogue

Classic Oxblood Cheltenham Brogue

(272)

Was $135.00 $69.00

Sale

Any 2 pairs for $120

Classic Suede Oxford Shoe

Classic Suede Oxford Shoe

(72)

Was $135.00 $69.00

Sale

Any 2 pairs for $120

Classic Oxford Shoe - Oxblood

Classic Oxford Shoe - Oxblood

(314)

Was $135.00 $69.00

Sale Classic Oxford Shoe - Tan

Classic Oxford Shoe - Tan

(374)

Was $135.00 $45.00

Sale

Any 2 pairs for $120

Classic Penny Loafer - Black Suede

Classic Penny Loafer - Black Suede

(70)

Was $135.00 $69.00

Sale

Any 2 pairs for $120

Classic Slip-On Boat Shoe

Classic Slip-On Boat Shoe

(405)

Was $135.00 $69.00

Sale

Any 2 pairs for $120

Classic Semi-Brogue - Black

Classic Semi-Brogue - Black

(4119)

Was $135.00 $69.00

Sale

Any 2 pairs for $120

Classic Boat Shoe

Classic Boat Shoe

(734)

Was $135.00 $69.00

Sale

Any 2 pairs for $120

Classic Penny Loafer - Dark Brown Suede

Classic Penny Loafer - Dark Brown Suede

(375)

Was $135.00 $69.00

Sale

Any 2 pairs for $120

Classic Penny Loafer - Brown Suede

Classic Penny Loafer - Brown Suede

(949)

Was $135.00 $69.00

Sale

Any 2 pairs for $120

Classic Oxford Shoe - Black

Classic Oxford Shoe - Black

(8242)

Was $135.00 $69.00

Sale

Any 2 Pairs for $140

Prestige Dress Shoe - Black

Prestige Dress Shoe - Black

(238)

Was $149.00 $75.00

Sale

Any 2 Pairs for $140

Prestige Oxford Dress Shoe - Black

Prestige Oxford Dress Shoe - Black

(122)

Was $149.00 $75.00

Sale Prestige Whitworth Brogue

Prestige Whitworth Brogue

(160)

Was $159.00 $79.00

Sale Prestige Bartlett Brogue - Tan

Prestige Bartlett Brogue - Tan

(121)

Was $159.00 $79.00

Sale Prestige Split Brogue - Two-Tone

Prestige Split Brogue - Two-Tone

(72)

Was $149.00 $59.00

Sale Prestige Whitworth Brogue - Black

Prestige Whitworth Brogue - Black

(75)

Was $159.00 $79.00

Sale Prestige Oxford Shoe - Rubber Sole

Prestige Oxford Shoe - Rubber Sole

(41)

Was $179.00 $59.00

Sale

Any 2 Pairs for $140

Prestige Leather Lace-Up Boat Shoe

Prestige Leather Lace-Up Boat Shoe

(390)

Was $149.00 $75.00

Sale

Any 2 Pairs for $140

Prestige Lace-Up Boat Shoe

Prestige Lace-Up Boat Shoe

(233)

Was $149.00 $75.00

Sale

Any 2 Pairs for $140

Prestige Boat Shoe

Prestige Boat Shoe

(265)

Was $149.00 $75.00

Sale Prestige Cumbria Boot

Prestige Cumbria Boot

(181)

Was $159.00 $79.00

Sale

Any 2 Pairs for $140

Prestige Twin Monk Shoe - Oxblood

Prestige Twin Monk Shoe - Oxblood

(122)

Was $149.00 $75.00

Sale

Any 2 Pairs for $140

Prestige Slip-On Boat Shoe - Brown

Prestige Slip-On Boat Shoe - Brown

(333)

Was $149.00 $75.00

Sale

Any 2 Pairs for $140

Prestige Slip-On Boat Shoe - Green

Prestige Slip-On Boat Shoe - Green

(326)

Was $149.00 $75.00

Sale

Any 2 Pairs for $140

Prestige Semi-Brogue

Prestige Semi-Brogue

(582)

Was $149.00 $75.00

Sale

Any 2 Pairs for $140

Prestige Oxford Shoe - Black

Prestige Oxford Shoe - Black

(796)

Was $149.00 $75.00

Sale Prestige Chelsea Boot

Prestige Chelsea Boot

(328)

Was $159.00 $79.00

Sale Prestige Chelsea Boot - Black

Prestige Chelsea Boot - Black

(1463)

Was $159.00 $79.00

Sale Classic Durham Shoe - Black

Classic Durham Shoe - Black

(150)

Was $135.00 $45.00

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