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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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Any 2 for $140

Prestige Suede Sneakers - Gray

Prestige Suede Sneakers - Gray

(4)

Was $149.00 $79.00

Any 2 for $140

Prestige Suede Sneakers - Navy

Prestige Suede Sneakers - Navy

(7)

Was $149.00 $79.00

Any 2 for $140

Prestige Suede Sneakers - Tan

Prestige Suede Sneakers - Tan

(3)

Was $149.00 $79.00

Sale Prestige Crepe Sole Chelsea Boots - Tan

Prestige Crepe Sole Chelsea Boots - Tan

(3)

Was $159.00 $85.00 $75.00 Save $10.00

Sale Prestige Crepe Sole Chelsea Boots - Navy

Prestige Crepe Sole Chelsea Boots - Navy

(0)

Was $159.00 $85.00 $75.00 Save $10.00

Sale Prestige Crepe Sole Desert Boots - Tan

Prestige Crepe Sole Desert Boots - Tan

(1)

Was $159.00 $85.00 $75.00 Save $10.00

Sale Prestige Crepe Sole Desert Boots - Navy

Prestige Crepe Sole Desert Boots - Navy

(3)

Was $159.00 $85.00 $75.00 Save $10.00

Sale Prestige Desert Boots - Gray

Prestige Desert Boots - Gray

(0)

Was $159.00 $85.00 $75.00 Save $10.00

Sale

Any 2 pairs for $125

Prestige Lightweight Derby - Navy Suede

Prestige Lightweight Derby - Navy Suede

(33)

Was $149.00 $75.00 $65.00 Save $10.00

Sale

Any 2 pairs for $125

Prestige Lightweight Derby - Tan

Prestige Lightweight Derby - Tan

(33)

Was $149.00 $75.00 $65.00 Save $10.00

Sale

Any 2 pairs for $125

Prestige Lightweight Derby - Tobacco

Prestige Lightweight Derby - Tobacco

(40)

Was $149.00 $75.00 $65.00 Save $10.00

Any 2 for $140

Prestige Boat Shoe - Gray

Prestige Boat Shoe - Gray

(401)

Was $149.00 $79.00

Any 2 for $140

Prestige Penny Loafer - Black

Prestige Penny Loafer - Black

(317)

Was $149.00 $79.00

Sale

Any 2 pairs for $125

Prestige Boat Shoe - Navy

Prestige Boat Shoe - Navy

(346)

Was $149.00 $75.00 $65.00 Save $10.00

Any 2 for $140

Prestige Boat Shoe - Tan

Prestige Boat Shoe - Tan

(401)

Was $149.00 $79.00

Any 2 for $140

Prestige Penny Loafer - Tan

Prestige Penny Loafer - Tan

(258)

Was $149.00 $79.00

Sale

Any 2 pairs for $125

Prestige Boat Shoe - Dark Olive

Prestige Boat Shoe - Dark Olive

(346)

Was $149.00 $75.00 $65.00 Save $10.00

Any 2 for $130

Classic Boat Shoe - Blue

Classic Boat Shoe - Blue

(42)

Was $135.00 $69.00

Any 2 for $130

Classic Boat Shoe - Tobacco

Classic Boat Shoe - Tobacco

(45)

Was $135.00 $69.00

Any 2 for $130

Classic Boat Shoe - Navy/Brown

Classic Boat Shoe - Navy/Brown

(127)

Was $135.00 $69.00

Sale Prestige Lightweight Derby - Tan

Prestige Lightweight Derby - Tan

(33)

Was $149.00 $45.00

Any 2 for $130

Classic Derby Shoe - Black

Classic Derby Shoe - Black

(43)

Was $135.00 $75.00

Any 2 for $130

Classic Derby Shoe - Suede

Classic Derby Shoe - Suede

(7)

Was $135.00 $75.00

Any 2 for $130

Classic Derby Shoe - Black Suede

Classic Derby Shoe - Black Suede

(12)

Was $135.00 $75.00

Any 2 for $130

Classic Chichester Shoe - Oxblood

Classic Chichester Shoe - Oxblood

(146)

Was $135.00 $69.00

Sale Prestige Derby Shoe - Tan

Prestige Derby Shoe - Tan

(15)

Was $159.00 $45.00

Sale Prestige Twin Monk Shoe - Tan

Prestige Twin Monk Shoe - Tan

(180)

Was $149.00 $45.00

Prestige Davington Brogue - Tan

(25)

Was $159.00 $89.00

Sale Prestige Fairfield Boots - Brown

Prestige Fairfield Boots - Brown

(22)

Was $159.00 $50.00

Prestige Chukka Boots - Tan

(29)

Was $189.00 $99.00

Sale Prestige Davington Brogue - Black

Prestige Davington Brogue - Black

(22)

Was $159.00 $80.00 $75.00 Save $5.00

Prestige Whitworth Brogue - Tan

(183)

Was $159.00 $75.00

Sale Prestige Oxford Shoe - Tan

Prestige Oxford Shoe - Tan

(8)

Was $159.00 $45.00

Sale Classic Slip-On Boat Shoe - Navy/Brown

Classic Slip-On Boat Shoe - Navy/Brown

(427)

Was $135.00 $65.00 $60.00 Save $5.00

Sale Classic Slip-On Boat Shoe - Camel

Classic Slip-On Boat Shoe - Camel

(427)

Was $135.00 $65.00 $60.00 Save $5.00

Prestige Country Boot In Tweed

(41)

Was $189.00 $115.00

Sale Classic Cheltenham Brogue In Suede - Mid Brown

Classic Cheltenham Brogue In Suede - Mid Brown

(65)

Was $135.00 $65.00 $60.00 Save $5.00

Any 2 for $130

Classic Chichester Shoe - Black

Classic Chichester Shoe - Black

(146)

Was $135.00 $69.00

Sale Classic Oxford Shoe - Tan

Classic Oxford Shoe - Tan

(399)

Was $135.00 $65.00 $60.00 Save $5.00

Sale Prestige Suede Chelsea Boot - Black

Prestige Suede Chelsea Boot - Black

(21)

Was $189.00 $55.00

Sale Prestige Suede Chelsea Boot - Brown

Prestige Suede Chelsea Boot - Brown

(35)

Was $189.00 $50.00

Prestige Leyton Boot - Burgundy

(34)

Was $159.00 $59.00

Prestige Monk Boot - Black

(32)

Was $159.00 $89.00

Prestige Country Boot - Black

(98)

Was $189.00 $99.00

Prestige Bartlett Brogue In Tweed

(43)

Was $189.00 $99.00

Any 2 for $130

Classic Oxblood Cheltenham Brogue

Classic Oxblood Cheltenham Brogue

(306)

Was $135.00 $69.00

Sale Classic Suede Oxford Shoe

Classic Suede Oxford Shoe

(77)

Was $135.00 $65.00 $60.00 Save $5.00

Any 2 for $130

Classic Oxford Shoe - Oxblood

Classic Oxford Shoe - Oxblood

(348)

Was $135.00 $69.00

Any 2 for $130

Classic Penny Loafer - Black Suede

Classic Penny Loafer - Black Suede

(76)

Was $135.00 $75.00

Any 2 for $130

Classic Slip-On Boat Shoe

Classic Slip-On Boat Shoe

(427)

Was $135.00 $69.00

Any 2 for $130

Classic Semi-Brogue - Black

Classic Semi-Brogue - Black

(4132)

Was $135.00 $69.00

Any 2 for $130

Classic Boat Shoe

Classic Boat Shoe

(751)

Was $135.00 $69.00

Any 2 for $130

Classic Penny Loafer - Dark Brown Suede

Classic Penny Loafer - Dark Brown Suede

(383)

Was $135.00 $75.00

Any 2 for $130

Classic Penny Loafer - Brown Suede

Classic Penny Loafer - Brown Suede

(957)

Was $135.00 $75.00

Any 2 for $130

Classic Oxford Shoe - Black

Classic Oxford Shoe - Black

(8319)

Was $135.00 $69.00

Any 2 for $140

Prestige Dress Shoe - Black

Prestige Dress Shoe - Black

(243)

Was $149.00 $79.00

Any 2 for $140

Prestige Oxford Dress Shoe - Black

Prestige Oxford Dress Shoe - Black

(129)

Was $149.00 $79.00

Sale Prestige Whitworth Brogue - Black

Prestige Whitworth Brogue - Black

(85)

Was $159.00 $85.00 $75.00 Save $10.00

Prestige Whitworth Brogue

(183)

Was $159.00 $89.00

Prestige Bartlett Brogue - Tan

(136)

Was $159.00 $89.00

Sale Prestige Oxford Shoe - Rubber Sole

Prestige Oxford Shoe - Rubber Sole

(46)

Was $179.00 $45.00

Any 2 for $140

Prestige Lace-Up Boat Shoe

Prestige Lace-Up Boat Shoe

(241)

Was $149.00 $79.00

Any 2 for $140

Prestige Leather Lace-Up Boat Shoe

Prestige Leather Lace-Up Boat Shoe

(401)

Was $149.00 $79.00

Any 2 for $140

Prestige Boat Shoe

Prestige Boat Shoe

(305)

Was $149.00 $79.00

Prestige Cumbria Boot

(188)

Was $159.00 $89.00

Any 2 for $140

Prestige Twin Monk Shoe - Oxblood

Prestige Twin Monk Shoe - Oxblood

(140)

Was $149.00 $79.00

Any 2 for $140

Prestige Slip-On Boat Shoe

Prestige Slip-On Boat Shoe

(334)

Was $149.00 $79.00

Any 2 for $140

Prestige Slip-On Boat Shoe - Brown

Prestige Slip-On Boat Shoe - Brown

(346)

Was $149.00 $79.00

Sale Prestige Semi-Brogue

Prestige Semi-Brogue

(590)

Was $149.00 $50.00

Any 2 for $140

Prestige Oxford Shoe - Black

Prestige Oxford Shoe - Black

(804)

Was $149.00 $79.00

Prestige Chelsea Boot - Black

(1480)

Was $159.00 $89.00

Prestige Chelsea Boot

(342)

Was $159.00 $89.00

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