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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

Any 2 for $120

Classic Oxford Shoe - Black

Classic Oxford Shoe - Black

(8327)

Was $135.00 $69.00 $65.00 Save $4.00

Sale

Any 2 for $120

Classic Oxford Shoe - Oxblood

Classic Oxford Shoe - Oxblood

(351)

Was $135.00 $69.00 $65.00 Save $4.00

Sale

Any 2 for $120

Classic Chichester Shoe - Black

Classic Chichester Shoe - Black

(155)

Was $135.00 $69.00 $65.00 Save $4.00

Sale

Any 2 for $120

Classic Oxblood Cheltenham Brogue

Classic Oxblood Cheltenham Brogue

(313)

Was $135.00 $69.00 $65.00 Save $4.00

Sale

Any 2 for $120

Classic Chichester Shoe - Oxblood

Classic Chichester Shoe - Oxblood

(155)

Was $135.00 $69.00 $65.00 Save $4.00

Sale

Any 2 pairs for $130

Prestige Twin Monk Shoe - Oxblood

Prestige Twin Monk Shoe - Oxblood

(143)

Was $149.00 $75.00 $72.50 Save $2.50

Sale

Any 2 for $120

Classic Derby Shoe - Black

Classic Derby Shoe - Black

(48)

Was $135.00 $75.00 $65.00 Save $10.00

Sale Prestige Whitworth Brogue

Prestige Whitworth Brogue

(184)

Was $159.00 $85.00 $80.00 Save $5.00

Sale Prestige Bartlett Brogue In Tweed

Prestige Bartlett Brogue In Tweed

(45)

Was $189.00 $89.00 $85.00 Save $4.00

Sale

Any 2 pairs for $130

Prestige Boat Shoe

Prestige Boat Shoe

(307)

Was $149.00 $75.00 $72.50 Save $2.50

Sale Prestige Country Boot - Black

Prestige Country Boot - Black

(100)

Was $189.00 $85.00 $80.00 Save $5.00

Sale

Any 2 pairs for $130

Prestige Dress Shoe - Black

Prestige Dress Shoe - Black

(244)

Was $149.00 $75.00 $72.50 Save $2.50

Sale

Any 2 for $120

Classic Derby Shoe - Black Suede

Classic Derby Shoe - Black Suede

(16)

Was $135.00 $75.00 $65.00 Save $10.00

Sale Prestige Chelsea Boot - Black

Prestige Chelsea Boot - Black

(1483)

Was $159.00 $85.00 $80.00 Save $5.00

Prestige Country Boot In Tweed

(41)

Was $189.00 $99.00

Sale

Any 2 for $120

Classic Oxford Shoe - Tan

Classic Oxford Shoe - Tan

(400)

Was $135.00 $69.00 $65.00 Save $4.00

Sale

Any 2 for $120

Classic Boat Shoe - Navy/Brown

Classic Boat Shoe - Navy/Brown

(128)

Was $135.00 $69.00 $65.00 Save $4.00

Sale

Any 2 for $120

Classic Penny Loafer - Black Suede

Classic Penny Loafer - Black Suede

(79)

Was $135.00 $75.00 $65.00 Save $10.00

Sale

Any 2 for $120

Classic Boat Shoe

Classic Boat Shoe

(751)

Was $135.00 $69.00 $65.00 Save $4.00

Sale

Any 2 pairs for $130

Prestige Slip-On Boat Shoe - Brown

Prestige Slip-On Boat Shoe - Brown

(350)

Was $149.00 $75.00 $72.50 Save $2.50

Sale

Any 2 pairs for $130

Prestige Leather Lace-Up Boat Shoe

Prestige Leather Lace-Up Boat Shoe

(403)

Was $149.00 $75.00 $72.50 Save $2.50

Sale

Any 2 for $120

Classic Slip-On Boat Shoe

Classic Slip-On Boat Shoe

(428)

Was $135.00 $69.00 $65.00 Save $4.00

Sale

Any 2 pairs for $130

Prestige Oxford Shoe - Black

Prestige Oxford Shoe - Black

(805)

Was $149.00 $75.00 $72.50 Save $2.50

Sale

Any 2 for $120

Classic Penny Loafer - Brown Suede

Classic Penny Loafer - Brown Suede

(958)

Was $135.00 $75.00 $65.00 Save $10.00

Sale

Any 2 pairs for $130

Prestige Penny Loafer - Tan

Prestige Penny Loafer - Tan

(261)

Was $149.00 $75.00 $72.50 Save $2.50

Sale

Any 2 pairs for $130

Prestige Slip-On Boat Shoe

Prestige Slip-On Boat Shoe

(339)

Was $149.00 $75.00 $72.50 Save $2.50

Sale Prestige Chukka Boots - Tan

Prestige Chukka Boots - Tan

(31)

Was $189.00 $85.00 $80.00 Save $5.00

Sale

Any 2 for $120

Classic Cheltenham Brogue In Suede - Mid Brown

Classic Cheltenham Brogue In Suede - Mid Brown

(68)

Was $135.00 $69.00 $65.00 Save $4.00

Sale

Any 2 pairs for $130

Prestige Suede Sneakers - Gray

Prestige Suede Sneakers - Gray

(5)

Was $149.00 $75.00 $72.50 Save $2.50

Sale

Any 2 for $120

Classic Suede Oxford Shoe

Classic Suede Oxford Shoe

(79)

Was $135.00 $69.00 $65.00 Save $4.00

Sale

Any 2 for $120

Classic Semi-Brogue - Black

Classic Semi-Brogue - Black

(4134)

Was $135.00 $69.00 $65.00 Save $4.00

Sale

Any 2 for $120

Classic Penny Loafer - Dark Brown Suede

Classic Penny Loafer - Dark Brown Suede

(384)

Was $135.00 $75.00 $65.00 Save $10.00

Sale

Any 2 pairs for $130

Prestige Suede Sneakers - Navy

Prestige Suede Sneakers - Navy

(7)

Was $149.00 $75.00 $72.50 Save $2.50

Sale Prestige Chelsea Boot

Prestige Chelsea Boot

(345)

Was $159.00 $85.00 $80.00 Save $5.00

Sale

Any 2 pairs for $130

Prestige Oxford Dress Shoe - Black

Prestige Oxford Dress Shoe - Black

(131)

Was $149.00 $75.00 $72.50 Save $2.50

Sale Prestige Bartlett Brogue - Tan

Prestige Bartlett Brogue - Tan

(140)

Was $159.00 $85.00 $80.00 Save $5.00

Sale

Any 2 pairs for $130

Prestige Boat Shoe - Gray

Prestige Boat Shoe - Gray

(403)

Was $149.00 $75.00 $72.50 Save $2.50

Sale

Any 2 for $120

Classic Derby Shoe - Suede

Classic Derby Shoe - Suede

(9)

Was $135.00 $75.00 $65.00 Save $10.00

Sale Prestige Chelsea Boot - Rubber Sole - Black

Prestige Chelsea Boot - Rubber Sole - Black

(30)

Was $189.00 $85.00 $80.00 Save $5.00

Sale

Any 2 pairs for $130

Prestige Lace-Up Boat Shoe

Prestige Lace-Up Boat Shoe

(241)

Was $149.00 $75.00 $72.50 Save $2.50

Sale

Any 2 pairs for $130

Prestige Suede Sneakers - Tan

Prestige Suede Sneakers - Tan

(7)

Was $149.00 $75.00 $72.50 Save $2.50

Sale Prestige Suede Chelsea Boot - Brown

Prestige Suede Chelsea Boot - Brown

(39)

Was $189.00 $50.00

Sale Prestige Semi-Brogue

Prestige Semi-Brogue

(591)

Was $149.00 $50.00

Sale Prestige Monk Boot - Black

Prestige Monk Boot - Black

(33)

Was $159.00 $85.00 $80.00 Save $5.00

Sale Prestige Lightweight Derby - Tan

Prestige Lightweight Derby - Tan

(38)

Was $149.00 $45.00

Sale

Any 2 pairs for $130

Prestige Boat Shoe - Tan

Prestige Boat Shoe - Tan

(403)

Was $149.00 $75.00 $72.50 Save $2.50

Sale Prestige Oxford Shoe - Rubber Sole

Prestige Oxford Shoe - Rubber Sole

(46)

Was $179.00 $45.00

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