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All Men's Leather Shoes

Handmade by master craftsmen, our men's leather shoes are comfortable, stylish, and designed to last. Whether you're looking for a pair of polished black Oxford shoes to wear with a suit, or a relaxed pair of brown brogues, good quality leather shoes from Samuel Windsor are a sound investment.

Sale

Buy 2 pairs for $120

Classic Oxford Shoe - Black

Classic Oxford Shoe - Black

(7398)

$69.00 $65.00 Save $4.00

Sale

Buy 2 pairs for $120

Classic Oxford Shoe - Oxblood

Classic Oxford Shoe - Oxblood

(189)

$69.00 $65.00 Save $4.00

Sale Prestige Country Boot - Black

Prestige Country Boot - Black

(37)

$85.00 $79.00 Save $6.00

Sale Prestige Bartlett Brogue In Tweed

Prestige Bartlett Brogue In Tweed

(8)

$89.00 $79.00 Save $10.00

Sale

Buy 2 pairs for $120

Classic Cheltenham Brogue

Classic Cheltenham Brogue

(170)

$69.00 $65.00 Save $4.00

Sale Prestige Whitworth Brogue

Prestige Whitworth Brogue

(107)

$79.00 $75.00 Save $4.00

Sale

Buy 2 pairs for $120

Classic Chichester Shoe - Black

Classic Chichester Shoe - Black

(35)

$69.00 $65.00 Save $4.00

Sale Prestige Country Boot In Tweed

Prestige Country Boot In Tweed

(5)

$89.00 $79.00 Save $10.00

Sale Prestige Chelsea Boot - Black

Prestige Chelsea Boot - Black

(1294)

$79.00 $75.00 Save $4.00

Sale Prestige Twin Monk Shoe - Oxblood

Prestige Twin Monk Shoe - Oxblood

(47)

$75.00 $70.00 Save $5.00

Sale Prestige Dress Shoe - Black

Prestige Dress Shoe - Black

(202)

$75.00 $70.00 Save $5.00

Sale

Buy 2 pairs for $120

Classic Oxford Shoe

Classic Oxford Shoe

(322)

$69.00 $65.00 Save $4.00

Sale

Buy 2 pairs for $120

Classic Penny Loafer

Classic Penny Loafer

(41)

$69.00 $65.00 Save $4.00

Sale

Buy 2 pairs for $120

Classic Penny Loafer

Classic Penny Loafer

(879)

$69.00 $65.00 Save $4.00

Sale

Buy 2 pairs for $120

Classic Suede Oxford Shoe

Classic Suede Oxford Shoe

(53)

$69.00 $65.00 Save $4.00

Sale Prestige Slip-On Boat Shoe

Prestige Slip-On Boat Shoe

(304)

$75.00 $70.00 Save $5.00

Sale Prestige Boat Shoe

Prestige Boat Shoe

(203)

$75.00 $70.00 Save $5.00

Sale

Buy 2 pairs for $120

Classic Slip-On Boat Shoe

Classic Slip-On Boat Shoe

(366)

$69.00 $65.00 Save $4.00

Sale Prestige Leather Lace-Up Boat Shoe

Prestige Leather Lace-Up Boat Shoe

(354)

$75.00 $70.00 Save $5.00

Sale Prestige Chelsea Boot

Prestige Chelsea Boot

(283)

$79.00 $75.00 Save $4.00

Sale Prestige Semi-Brogue

Prestige Semi-Brogue

(547)

$75.00 $70.00 Save $5.00

Sale

Buy 2 pairs for $120

Classic Penny Loafer

Classic Penny Loafer

(335)

$69.00 $65.00 Save $4.00

Sale Prestige Split Brogue

Prestige Split Brogue

(43)

$79.00 $75.00 Save $4.00

Sale Prestige Monk Boot - Black

Prestige Monk Boot - Black

(13)

$79.00 $75.00 Save $4.00

Sale Prestige Slip-On Boat Shoe

Prestige Slip-On Boat Shoe

(301)

$75.00 $70.00 Save $5.00

Sale Prestige Oxford Shoe - Black

Prestige Oxford Shoe - Black

(723)

$75.00 $70.00 Save $5.00

Sale

Buy 2 pairs for $120

Classic Semi-Brogue - Black

Classic Semi-Brogue - Black

(3755)

$69.00 $65.00 Save $4.00

Sale Prestige Bartlett Brogue

Prestige Bartlett Brogue

(70)

$85.00 $79.00 Save $6.00

Sale Prestige Bartlett Brogue In Suede - Mid Brown

Prestige Bartlett Brogue In Suede - Mid Brown

(3)

$85.00 $79.00 Save $6.00

Sale Prestige Cumbria Boot

Prestige Cumbria Boot

(149)

$79.00 $75.00 Save $4.00

Sale Prestige Suede Chelsea Boot - Brown

Prestige Suede Chelsea Boot - Brown

(5)

$85.00 $79.00 Save $6.00

Sale Prestige Whitworth Brogue - Black

Prestige Whitworth Brogue - Black

(48)

$79.00 $75.00 Save $4.00

Sale Prestige Oxford Shoe - Rubber Sole

Prestige Oxford Shoe - Rubber Sole

(17)

$85.00 $79.00 Save $6.00

Sale Prestige Suede Chelsea Boot - Black

Prestige Suede Chelsea Boot - Black

(3)

$85.00 $79.00 Save $6.00

Sale Prestige Leyton Boot - Burgundy

Prestige Leyton Boot - Burgundy

(10)

$79.00 $75.00 Save $4.00

Sale

Buy 2 pairs for $120

Classic Cheltenham Brogue In Suede - Mid Brown

Classic Cheltenham Brogue In Suede - Mid Brown

(24)

$69.00 $65.00 Save $4.00

Sale

Buy 2 pairs for $120

Classic Boat Shoe

Classic Boat Shoe

(631)

$69.00 $65.00 Save $4.00

Sale Prestige Lace-Up Boat Shoe

Prestige Lace-Up Boat Shoe

(205)

$75.00 $70.00 Save $5.00

Sale Prestige Oxford Dress Shoe - Black

Prestige Oxford Dress Shoe - Black

(81)

$75.00 $70.00 Save $5.00

Sale

Buy 2 pairs for $120

Classic Durham Shoe - Black

Classic Durham Shoe - Black

(99)

$69.00 $65.00 Save $4.00

Sale

Buy 2 pairs for $120

Classic Boat Shoe - Navy/Brown

Classic Boat Shoe - Navy/Brown

(50)

$69.00 $65.00 Save $4.00

Sale Classic Boat Shoe - Blue
Sale Classic Monk Shoe

Classic Monk Shoe

(23)

$59.00

Sale Prestige Bartlett Brogue

Prestige Bartlett Brogue

(13)

$85.00 $79.00 Save $6.00