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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 pairs for $130

Prestige Suede Sneakers - Gray

Prestige Suede Sneakers - Gray

(2)

Was $149.00 $75.00 $69.00 Save $6.00

Sale

Any 2 pairs for $130

Prestige Suede Sneakers - Navy

Prestige Suede Sneakers - Navy

(5)

Was $149.00 $75.00 $69.00 Save $6.00

Sale

Any 2 pairs for $130

Prestige Suede Sneakers - Tan

Prestige Suede Sneakers - Tan

(2)

Was $149.00 $75.00 $69.00 Save $6.00

Sale Prestige Crepe Sole Chelsea Boots - Tan

Prestige Crepe Sole Chelsea Boots - Tan

(0)

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

(0)

Was $159.00 $85.00 $75.00 Save $10.00

Sale Prestige Crepe Sole Desert Boots - Navy

Prestige Crepe Sole Desert Boots - Navy

(1)

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 $130

Prestige Lightweight Derby - Navy Suede

Prestige Lightweight Derby - Navy Suede

(32)

Was $149.00 $75.00 $69.00 Save $6.00

Sale

Any 2 pairs for $130

Prestige Lightweight Derby - Tan

Prestige Lightweight Derby - Tan

(32)

Was $149.00 $75.00 $69.00 Save $6.00

Sale

Any 2 pairs for $130

Prestige Lightweight Derby - Tobacco

Prestige Lightweight Derby - Tobacco

(39)

Was $149.00 $75.00 $69.00 Save $6.00

Sale

Any 2 pairs for $130

Prestige Boat Shoe - Gray

Prestige Boat Shoe - Gray

(399)

Was $149.00 $75.00 $69.00 Save $6.00

Sale

Any 2 pairs for $130

Prestige Penny Loafer - Black

Prestige Penny Loafer - Black

(315)

Was $149.00 $75.00 $69.00 Save $6.00

Sale

Any 2 pairs for $130

Prestige Boat Shoe - Navy

Prestige Boat Shoe - Navy

(341)

Was $149.00 $75.00 $69.00 Save $6.00

Sale

Any 2 pairs for $130

Prestige Boat Shoe - Tan

Prestige Boat Shoe - Tan

(399)

Was $149.00 $75.00 $69.00 Save $6.00

Sale

Any 2 pairs for $130

Prestige Penny Loafer - Tan

Prestige Penny Loafer - Tan

(257)

Was $149.00 $75.00 $69.00 Save $6.00

Sale

Any 2 pairs for $130

Prestige Boat Shoe - Dark Olive

Prestige Boat Shoe - Dark Olive

(341)

Was $149.00 $75.00 $69.00 Save $6.00

Sale

Any 2 pairs for $120

Classic Boat Shoe - Blue

Classic Boat Shoe - Blue

(41)

Was $135.00 $65.00

Sale

Any 2 pairs for $120

Classic Boat Shoe - Tobacco

Classic Boat Shoe - Tobacco

(45)

Was $135.00 $65.00

Sale

Any 2 pairs for $120

Classic Boat Shoe - Navy/Brown

Classic Boat Shoe - Navy/Brown

(121)

Was $135.00 $65.00

Sale Prestige Lightweight Derby - Tan

Prestige Lightweight Derby - Tan

(32)

Was $149.00 $45.00

Sale

Any 2 pairs for $120

Classic Derby Shoe - Black Suede

Classic Derby Shoe - Black Suede

(11)

Was $135.00 $70.00 $65.00 Save $5.00

Sale

Any 2 pairs for $120

Classic Derby Shoe - Black

Classic Derby Shoe - Black

(39)

Was $135.00 $70.00 $65.00 Save $5.00

Sale

Any 2 pairs for $120

Classic Derby Shoe - Suede

Classic Derby Shoe - Suede

(6)

Was $135.00 $70.00 $65.00 Save $5.00

Sale

Any 2 pairs for $120

Classic Chichester Shoe - Oxblood

Classic Chichester Shoe - Oxblood

(142)

Was $135.00 $65.00 $62.50 Save $2.50

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

(28)

Was $189.00 $95.00 $79.00 Save $16.00

Sale Prestige Twin Monk Shoe - Tan

Prestige Twin Monk Shoe - Tan

(174)

Was $149.00 $45.00

Sale Prestige Davington Brogue - Tan

Prestige Davington Brogue - Tan

(24)

Was $159.00 $85.00 $75.00 Save $10.00

Sale Prestige Boat Shoe - Camel

Prestige Boat Shoe - Camel

(300)

Was $149.00 $40.00

Sale Prestige Fairfield Boots - Brown

Prestige Fairfield Boots - Brown

(21)

Was $159.00 $50.00

Sale Prestige Chukka Boots - Tan

Prestige Chukka Boots - Tan

(29)

Was $189.00 $95.00 $79.00 Save $16.00

Sale Prestige Davington Brogue - Black

Prestige Davington Brogue - Black

(22)

Was $159.00 $80.00 $75.00 Save $5.00

Prestige Whitworth Brogue - Tan

(181)

Was $159.00 $75.00

Sale Prestige Oxford Shoe - Tan

Prestige Oxford Shoe - Tan

(7)

Was $159.00 $45.00

Sale

Any 2 pairs for $120

Classic Slip-On Boat Shoe - Navy/Brown

Classic Slip-On Boat Shoe - Navy/Brown

(425)

Was $135.00 $65.00

Sale

Any 2 pairs for $120

Classic Slip-On Boat Shoe - Camel

Classic Slip-On Boat Shoe - Camel

(425)

Was $135.00 $65.00

Sale Prestige Boat Shoe - Navy

Prestige Boat Shoe - Navy

(300)

Was $149.00 $40.00

Sale Prestige Country Boot In Tweed

Prestige Country Boot In Tweed

(41)

Was $189.00 $110.00 $89.00 Save $21.00

Sale

Any 2 pairs for $120

Classic Cheltenham Brogue In Suede - Mid Brown

Classic Cheltenham Brogue In Suede - Mid Brown

(64)

Was $135.00 $65.00 $62.50 Save $2.50

Sale

Any 2 pairs for $120

Classic Chichester Shoe - Black

Classic Chichester Shoe - Black

(142)

Was $135.00 $65.00 $62.50 Save $2.50

Sale

Any 2 pairs for $120

Classic Oxford Shoe - Tan

Classic Oxford Shoe - Tan

(398)

Was $135.00 $65.00 $62.50 Save $2.50

Sale Prestige Suede Chelsea Boot - Black

Prestige Suede Chelsea Boot - Black

(18)

Was $189.00 $55.00

Sale Prestige Suede Chelsea Boot - Brown

Prestige Suede Chelsea Boot - Brown

(30)

Was $189.00 $50.00

Prestige Leyton Boot - Burgundy

(34)

Was $159.00 $59.00

Sale Prestige Monk Boot - Black

Prestige Monk Boot - Black

(32)

Was $159.00 $50.00

Sale Prestige Country Boot - Black

Prestige Country Boot - Black

(94)

Was $189.00 $55.00

Sale Prestige Bartlett Brogue In Tweed

Prestige Bartlett Brogue In Tweed

(42)

Was $189.00 $95.00 $79.00 Save $16.00

Sale

Any 2 pairs for $120

Classic Oxblood Cheltenham Brogue

Classic Oxblood Cheltenham Brogue

(303)

Was $135.00 $65.00 $62.50 Save $2.50

Sale

Any 2 pairs for $120

Classic Suede Oxford Shoe

Classic Suede Oxford Shoe

(76)

Was $135.00 $65.00 $62.50 Save $2.50

Sale

Any 2 pairs for $120

Classic Oxford Shoe - Oxblood

Classic Oxford Shoe - Oxblood

(343)

Was $135.00 $65.00 $62.50 Save $2.50

Sale

Any 2 pairs for $120

Classic Penny Loafer - Black Suede

Classic Penny Loafer - Black Suede

(75)

Was $135.00 $70.00 $65.00 Save $5.00

Sale

Any 2 pairs for $120

Classic Slip-On Boat Shoe

Classic Slip-On Boat Shoe

(425)

Was $135.00 $65.00

Sale

Any 2 pairs for $120

Classic Semi-Brogue - Black

Classic Semi-Brogue - Black

(4130)

Was $135.00 $65.00 $62.50 Save $2.50

Sale

Any 2 pairs for $120

Classic Boat Shoe

Classic Boat Shoe

(747)

Was $135.00 $65.00

Sale

Any 2 pairs for $120

Classic Penny Loafer - Dark Brown Suede

Classic Penny Loafer - Dark Brown Suede

(383)

Was $135.00 $70.00 $65.00 Save $5.00

Sale

Any 2 pairs for $120

Classic Penny Loafer - Brown Suede

Classic Penny Loafer - Brown Suede

(955)

Was $135.00 $70.00 $65.00 Save $5.00

Sale

Any 2 pairs for $120

Classic Oxford Shoe - Black

Classic Oxford Shoe - Black

(8310)

Was $135.00 $65.00 $62.50 Save $2.50

Sale

Any 2 pairs for $130

Prestige Dress Shoe - Black

Prestige Dress Shoe - Black

(242)

Was $149.00 $75.00 $69.00 Save $6.00

Sale

Any 2 pairs for $130

Prestige Oxford Dress Shoe - Black

Prestige Oxford Dress Shoe - Black

(129)

Was $149.00 $75.00 $69.00 Save $6.00

Sale Prestige Whitworth Brogue - Black

Prestige Whitworth Brogue - Black

(84)

Was $159.00 $85.00 $75.00 Save $10.00

Sale Prestige Whitworth Brogue

Prestige Whitworth Brogue

(181)

Was $159.00 $85.00 $75.00 Save $10.00

Sale Prestige Bartlett Brogue - Tan

Prestige Bartlett Brogue - Tan

(135)

Was $159.00 $85.00 $75.00 Save $10.00

Sale Prestige Oxford Shoe - Rubber Sole

Prestige Oxford Shoe - Rubber Sole

(45)

Was $179.00 $45.00

Sale

Any 2 pairs for $130

Prestige Lace-Up Boat Shoe

Prestige Lace-Up Boat Shoe

(237)

Was $149.00 $75.00 $69.00 Save $6.00

Sale

Any 2 pairs for $130

Prestige Leather Lace-Up Boat Shoe

Prestige Leather Lace-Up Boat Shoe

(399)

Was $149.00 $75.00 $69.00 Save $6.00

Sale

Any 2 pairs for $130

Prestige Boat Shoe

Prestige Boat Shoe

(300)

Was $149.00 $75.00 $69.00 Save $6.00

Sale Prestige Cumbria Boot

Prestige Cumbria Boot

(187)

Was $159.00 $85.00 $75.00 Save $10.00

Sale

Any 2 pairs for $130

Prestige Twin Monk Shoe - Oxblood

Prestige Twin Monk Shoe - Oxblood

(137)

Was $149.00 $75.00 $69.00 Save $6.00

Sale

Any 2 pairs for $130

Prestige Slip-On Boat Shoe

Prestige Slip-On Boat Shoe

(331)

Was $149.00 $75.00 $69.00 Save $6.00

Sale

Any 2 pairs for $130

Prestige Slip-On Boat Shoe - Brown

Prestige Slip-On Boat Shoe - Brown

(341)

Was $149.00 $75.00 $69.00 Save $6.00

Sale Prestige Semi-Brogue

Prestige Semi-Brogue

(588)

Was $149.00 $50.00

Sale

Any 2 pairs for $130

Prestige Oxford Shoe - Black

Prestige Oxford Shoe - Black

(802)

Was $149.00 $75.00 $69.00 Save $6.00

Sale Prestige Chelsea Boot - Black

Prestige Chelsea Boot - Black

(1480)

Was $159.00 $85.00 $75.00 Save $10.00

Sale Prestige Chelsea Boot

Prestige Chelsea Boot

(342)

Was $159.00 $85.00 $75.00 Save $10.00

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