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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 Cumbria Boot

    Prestige Cumbria Boot

    (190)

    Was $159.00 $85.00 $80.00 Save $5.00

    Sale Prestige Davington Brogue - Black

    Prestige Davington Brogue - Black

    (22)

    Was $159.00 $85.00 $80.00 Save $5.00

    Sale Prestige Davington Brogue - Tan

    Prestige Davington Brogue - Tan

    (26)

    Was $159.00 $85.00 $80.00 Save $5.00

    Sale Prestige Suede Chelsea Boot - Black

    Prestige Suede Chelsea Boot - Black

    (27)

    Was $189.00 $55.00

    Sale

    Any 2 pairs for $130

    Prestige Penny Loafer - Black

    Prestige Penny Loafer - Black

    (319)

    Was $149.00 $75.00 $72.50 Save $2.50

    Prestige Crepe Sole Chelsea Boots - Tan

    Prestige Crepe Sole Chelsea Boots - Tan

    (4)

    Was $159.00 $75.00

    Sale Prestige Bartlett Brogue In Suede - Mid Brown

    Prestige Bartlett Brogue In Suede - Mid Brown

    (38)

    Was $149.00 $45.00

    Prestige Desert Boots - Gray

    Prestige Desert Boots - Gray

    (1)

    Was $159.00 $75.00

    Sale Prestige Whitworth Brogue - Black

    Prestige Whitworth Brogue - Black

    (85)

    Was $159.00 $85.00 $80.00 Save $5.00

    Sale

    Any 2 pairs for $130

    Prestige Lightweight Derby - Tan

    Prestige Lightweight Derby - Tan

    (38)

    Was $149.00 $75.00 $72.50 Save $2.50

    Sale

    Any 2 pairs for $130

    Prestige Lightweight Derby - Tobacco

    Prestige Lightweight Derby - Tobacco

    (41)

    Was $149.00 $75.00 $72.50 Save $2.50

    Sale

    Any 2 for $120

    Classic Boat Shoe - Tobacco

    Classic Boat Shoe - Tobacco

    (45)

    Was $135.00 $69.00 $65.00 Save $4.00

    Sale

    Any 2 pairs for $130

    Prestige Lightweight Derby - Navy Suede

    Prestige Lightweight Derby - Navy Suede

    (38)

    Was $149.00 $75.00 $72.50 Save $2.50

    Sale

    Any 2 for $120

    Classic Slip-On Boat Shoe - Navy/Brown

    Classic Slip-On Boat Shoe - Navy/Brown

    (428)

    Was $135.00 $69.00 $65.00 Save $4.00

    Sale

    Any 2 for $120

    Classic Slip-On Boat Shoe - Camel

    Classic Slip-On Boat Shoe - Camel

    (428)

    Was $135.00 $69.00 $65.00 Save $4.00

    Prestige Whitworth Brogue - Tan

    Prestige Whitworth Brogue - Tan

    (184)

    Was $159.00 $75.00

    Sale

    Any 2 pairs for $130

    Prestige Boat Shoe - Navy

    Prestige Boat Shoe - Navy

    (350)

    Was $149.00 $75.00 $72.50 Save $2.50

    Prestige Crepe Sole Desert Boots - Navy

    Prestige Crepe Sole Desert Boots - Navy

    (3)

    Was $159.00 $75.00

    Classic Durham Shoe - Black

    Classic Durham Shoe - Black

    (150)

    Was $135.00 $45.00

    Sale

    Any 2 for $120

    Classic Boat Shoe - Blue

    Classic Boat Shoe - Blue

    (42)

    Was $135.00 $69.00 $65.00 Save $4.00

    Sale

    Any 2 pairs for $130

    Prestige Boat Shoe - Dark Olive

    Prestige Boat Shoe - Dark Olive

    (350)

    Was $149.00 $75.00 $72.50 Save $2.50

    Prestige Slip-On Boat Shoe - Brown

    Prestige Slip-On Boat Shoe - Brown

    (19)

    Was $149.00 $50.00

    Prestige Leyton Boot - Burgundy

    Prestige Leyton Boot - Burgundy

    (34)

    Was $159.00 $59.00

    Prestige Crepe Sole Chelsea Boots - Navy

    Prestige Crepe Sole Chelsea Boots - Navy

    (0)

    Was $159.00 $75.00

    Sale Prestige Tweed Brogue Boot – Dartmoor

    Prestige Tweed Brogue Boot – Dartmoor

    (0)

    Was $189.00 $99.00 $95.00 Save $4.00

    Sale Prestige Tweed Brogue - Exmoor

    Prestige Tweed Brogue - Exmoor

    (1)

    Was $189.00 $89.00 $85.00 Save $4.00

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