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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 Prestige Tweed Brogue - Exmoor

Prestige Tweed Brogue - Exmoor

(7)

Was $189.00 $69.00 $60.00 Save $9.00

Sale Prestige Tweed Brogue Boot – Dartmoor

Prestige Tweed Brogue Boot – Dartmoor

(1)

Was $189.00 $75.00 $65.00 Save $10.00

Sale Prestige Suede Sneakers - Tan

Prestige Suede Sneakers - Tan

(8)

Was $149.00 $65.00 $55.00 Save $10.00

Sale Prestige Suede Sneakers - Gray

Prestige Suede Sneakers - Gray

(7)

Was $149.00 $65.00 $55.00 Save $10.00

Sale Prestige Suede Sneakers - Navy

Prestige Suede Sneakers - Navy

(10)

Was $149.00 $65.00 $55.00 Save $10.00

Prestige Desert Boots - Gray

(2)

Was $159.00 $89.00

Prestige Lightweight Derby - Tan

(39)

Was $149.00 $85.00

Prestige Lightweight Derby - Tobacco

(41)

Was $149.00 $85.00

Sale

Any 2 pairs for $90

Prestige Boat Shoe - Gray

Prestige Boat Shoe - Gray

(410)

Was $149.00 $65.00 $50.00 Save $15.00

Sale

Any 2 pairs for $90

Prestige Penny Loafer - Black

Prestige Penny Loafer - Black

(322)

Was $149.00 $65.00 $50.00 Save $15.00

Sale

Any 2 pairs for $90

Prestige Boat Shoe - Tan

Prestige Boat Shoe - Tan

(410)

Was $149.00 $65.00 $50.00 Save $15.00

Sale

Any 2 pairs for $90

Prestige Boat Shoe - Navy

Prestige Boat Shoe - Navy

(353)

Was $149.00 $65.00 $50.00 Save $15.00

Sale

Any 2 pairs for $90

Prestige Penny Loafer - Tan

Prestige Penny Loafer - Tan

(266)

Was $149.00 $65.00 $50.00 Save $15.00

Sale

Any 2 pairs for $90

Prestige Boat Shoe - Dark Olive

Prestige Boat Shoe - Dark Olive

(353)

Was $149.00 $75.00 $50.00 Save $25.00

Sale

Any 2 Pairs For $80

Classic Boat Shoe - Blue

Classic Boat Shoe - Blue

(45)

Was $135.00 $55.00 $45.00 Save $10.00

Sale

Any 2 Pairs For $80

Classic Boat Shoe - Tobacco

Classic Boat Shoe - Tobacco

(46)

Was $135.00 $55.00 $45.00 Save $10.00

Sale

Any 2 Pairs For $80

Classic Boat Shoe - Navy/Brown

Classic Boat Shoe - Navy/Brown

(131)

Was $135.00 $55.00 $45.00 Save $10.00

Sale Prestige Lightweight Derby - Tan

Prestige Lightweight Derby - Tan

(39)

Was $149.00 $45.00

Sale

Any 2 Pairs For $80

Classic Derby Shoe - Suede

Classic Derby Shoe - Suede

(12)

Was $135.00 $55.00 $45.00 Save $10.00

Sale

Any 2 Pairs For $80

Classic Derby Shoe - Black Suede

Classic Derby Shoe - Black Suede

(19)

Was $135.00 $55.00 $45.00 Save $10.00

Sale

Any 2 Pairs For $80

Classic Derby Shoe - Black

Classic Derby Shoe - Black

(58)

Was $135.00 $55.00 $45.00 Save $10.00

Sale

Any 2 Pairs For $80

Classic Chichester Shoe - Oxblood

Classic Chichester Shoe - Oxblood

(167)

Was $135.00 $55.00 $45.00 Save $10.00

Sale Prestige Derby Shoe - Tan

Prestige Derby Shoe - Tan

(15)

Was $159.00 $45.00

Sale Prestige Chelsea Boot - Rubber Sole - Black

Prestige Chelsea Boot - Rubber Sole - Black

(31)

Was $189.00 $69.00 $60.00 Save $9.00

Sale Prestige Davington Brogue - Tan

Prestige Davington Brogue - Tan

(27)

Was $159.00 $65.00 $55.00 Save $10.00

Sale Prestige Chukka Boots - Tan

Prestige Chukka Boots - Tan

(33)

Was $189.00 $85.00 $80.00 Save $5.00

Sale Prestige Davington Brogue - Black

Prestige Davington Brogue - Black

(22)

Was $159.00 $85.00 $72.50 Save $12.50

Prestige Whitworth Brogue - Tan

(187)

Was $159.00 $75.00

Sale Classic Slip-On Boat Shoe - Camel

Classic Slip-On Boat Shoe - Camel

(431)

Was $135.00 $69.00 $65.00 Save $4.00

Prestige Slip-On Boat Shoe - Brown

(19)

Was $149.00 $50.00

Prestige Country Boot In Tweed

(42)

Was $189.00 $95.00

Sale

Any 2 Pairs For $100

Classic Cheltenham Brogue In Suede - Mid Brown

Classic Cheltenham Brogue In Suede - Mid Brown

(70)

Was $135.00 $69.00 $65.00 Save $4.00

Sale

Any 2 Pairs For $80

Classic Chichester Shoe - Black

Classic Chichester Shoe - Black

(167)

Was $135.00 $55.00 $45.00 Save $10.00

Sale Classic Oxford Shoe - Tan

Classic Oxford Shoe - Tan

(400)

Was $135.00 $69.00 $65.00 Save $4.00

Sale Prestige Suede Chelsea Boot - Black

Prestige Suede Chelsea Boot - Black

(27)

Was $189.00 $55.00

Sale Prestige Monk Boot - Black

Prestige Monk Boot - Black

(34)

Was $159.00 $85.00 $72.50 Save $12.50

Sale Prestige Country Boot - Black

Prestige Country Boot - Black

(106)

Was $189.00 $85.00 $80.00 Save $5.00

Sale Prestige Bartlett Brogue In Tweed

Prestige Bartlett Brogue In Tweed

(46)

Was $189.00 $89.00 $85.00 Save $4.00

Sale

Any 2 Pairs For $80

Classic Oxblood Cheltenham Brogue

Classic Oxblood Cheltenham Brogue

(316)

Was $135.00 $55.00 $45.00 Save $10.00

Sale

Any 2 Pairs For $100

Classic Suede Oxford Shoe

Classic Suede Oxford Shoe

(79)

Was $135.00 $69.00 $65.00 Save $4.00

Sale

Any 2 Pairs For $80

Classic Oxford Shoe - Oxblood

Classic Oxford Shoe - Oxblood

(370)

Was $135.00 $55.00 $45.00 Save $10.00

Sale

Any 2 Pairs For $80

Classic Penny Loafer - Black Suede

Classic Penny Loafer - Black Suede

(83)

Was $135.00 $55.00 $45.00 Save $10.00

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