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“penny loafers and Men” we found 432 items!

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View More Like This Cole Haan - Howland Penny
Cole Haan Howland Penny $118.90 Rated: 4 stars!
View More Like This Rockport - Classic Loafer Lite Penny
Rockport Classic Loafer Lite Penny $99.95 Rated: 4 stars!
View More Like This Born - Simon
Born Simon $110.00 $90.00 Rated: 4 stars!
View More Like This Florsheim - Berkley Penny Loafer
Florsheim Berkley Penny Loafer $109.95 Rated: 4 stars!

View More Like This Rockport - Classic Loafer Lite Penny
Rockport Classic Loafer Lite Penny $99.95 Rated: 4 stars!
View More Like This Nunn Bush - Lincoln Penny Loafer
Nunn Bush Lincoln Penny Loafer $80.00 $64.00 Rated: 4 stars!
View More Like This Florsheim - Berkley Penny Loafer
Florsheim Berkley Penny Loafer $109.95 Rated: 4 stars!
View More Like This Sebago - Sloop
Sebago Sloop $119.95 Rated: 5 stars!

View More Like This Cole Haan - Pinch Penny
Cole Haan Pinch Penny $100.00 Rated: 4 stars!
View More Like This Rockport - Classic Loafer Lite Penny
Rockport Classic Loafer Lite Penny $99.95 Rated: 4 stars!
View More Like This Nunn Bush - Lincoln Penny Loafer
Nunn Bush Lincoln Penny Loafer $80.00 $64.00 Rated: 4 stars!
View More Like This Rockport - Oaklawn Park Penny
Rockport Oaklawn Park Penny $99.95 Rated: 4 stars!

View More Like This Cole Haan - Pinch Friday Contemporary
Cole Haan Pinch Friday Contemporary $130.00 $117.99 Rated: 5 stars!
View More Like This Cole Haan - Pinch Friday Contemporary
Cole Haan Pinch Friday Contemporary $130.00 $117.99 Rated: 5 stars!
View More Like This Johnston & Murphy - Beckwith Penny
Johnston & Murphy Beckwith Penny $135.00 Rated: 4 stars!
View More Like This Cole Haan - Pinch Penny
Cole Haan Pinch Penny $100.00 Rated: 4 stars!

View More Like This Cole Haan - Pinch Weekender Textile
Cole Haan Pinch Weekender Textile $90.00 $80.99 Rated: 5 stars!
View More Like This Florsheim - Jet Penny Slip-On
Florsheim Jet Penny Slip-On $124.95 Rated: 5 stars!
View More Like This Rockport - Oaklawn Park Penny
Rockport Oaklawn Park Penny $99.95 Rated: 4 stars!
View More Like This Cole Haan - Pinch Friday Contemporary
Cole Haan Pinch Friday Contemporary $130.00 $117.99 Rated: 5 stars!

View More Like This Cole Haan - Pinch Weekender Hand Stain
Cole Haan Pinch Weekender Hand Stain $130.00 Rated: 5 stars!
View More Like This Florsheim - Oval Penny Driver
Florsheim Oval Penny Driver $99.95 Rated: 5 stars!
View More Like This Sperry - Gold Sport Casual Penny w/ ASV
Sperry Gold Sport Casual Penny w/ ASV $155.00
View More Like This Johnston & Murphy - Beckwith Penny
Johnston & Murphy Beckwith Penny $135.00 Rated: 4 stars!

View More Like This Cole Haan - Howland Penny
Cole Haan Howland Penny $118.90 Rated: 4 stars!
View More Like This Cole Haan - Hamilton Grand Penny
Cole Haan Hamilton Grand Penny $280.00
View More Like This Florsheim - Oval Penny Driver
Florsheim Oval Penny Driver $99.95 Rated: 5 stars!
View More Like This Nunn Bush - Noah Beef Roll Penny Slip-On
Nunn Bush Noah Beef Roll Penny Slip-On $85.00 $68.00 Rated: 5 stars!

View More Like This Cole Haan - Pinch Weekender Textile
Cole Haan Pinch Weekender Textile $90.00 $72.99 Rated: 5 stars!
View More Like This Rockport - Classic Move Penny
Rockport Classic Move Penny $109.95 $99.95 Rated: 5 stars!
View More Like This ECCO - Hybrid Casual Penny
ECCO Hybrid Casual Penny $150.00
View More Like This Rockport - Modern Prep Penny
Rockport Modern Prep Penny $109.95 $99.95 Rated: 5 stars!

View More Like This Johnston & Murphy - Ainsworth Penny
Johnston & Murphy Ainsworth Penny $145.00 Rated: 4 stars!
View More Like This Johnston & Murphy - Ainsworth Penny
Johnston & Murphy Ainsworth Penny $145.00 Rated: 4 stars!
View More Like This Rockport - Modern Prep Penny
Rockport Modern Prep Penny $109.95 $99.95 Rated: 5 stars!
View More Like This Rockport - Oak Knoll - Shakespeare Circle
Rockport Oak Knoll - Shakespeare Circle $119.95 Rated: 5 stars!

View More Like This Florsheim - Oval Penny Driver
Florsheim Oval Penny Driver $99.95 Rated: 5 stars!
View More Like This Cole Haan - Pinch Weekender
Cole Haan Pinch Weekender $100.00 Rated: 4 stars!
View More Like This Cole Haan - Pinch Weekender
Cole Haan Pinch Weekender $100.00 $79.99 Rated: 4 stars!
View More Like This Allen-Edmonds - Daytona
Allen-Edmonds Daytona $195.00 Rated: 4 stars!

View More Like This Rockport - Classic Move Penny
Rockport Classic Move Penny $109.95 $99.95 Rated: 5 stars!
View More Like This Florsheim - Oval Penny Driver
Florsheim Oval Penny Driver $99.95 Rated: 5 stars!
View More Like This Cole Haan - Pinch Grand Penny
Cole Haan Pinch Grand Penny $170.00 Rated: 5 stars!
View More Like This Nunn Bush - Appleton Moc Toe Penny Loafer
Nunn Bush Appleton Moc Toe Penny Loafer $85.00 $68.00 Rated: 5 stars!

View More Like This Allen-Edmonds - Sedona
Allen-Edmonds Sedona $195.00
View More Like This Florsheim - Oval Penny Driver
Florsheim Oval Penny Driver $99.95 Rated: 5 stars!
G.H. Bass & Co. - Warrick
G.H. Bass & Co. Warrick $100.00
NEW!
View More Like This Allen-Edmonds - Lake Forest
Allen-Edmonds Lake Forest $395.00 Rated: 5 stars!

View More Like This Cole Haan - Hamilton Grand Penny
Cole Haan Hamilton Grand Penny $280.00
Massimo Matteo - Penny Classic
Massimo Matteo Penny Classic $99.00
NEW!
View More Like This Sperry - Gold Sport Casual Penny w/ ASV
Sperry Gold Sport Casual Penny w/ ASV $155.00
View More Like This Allen-Edmonds - Cavanaugh
Allen-Edmonds Cavanaugh $275.00 Rated: 3 stars!

View More Like This Rockport - Oak Knoll - Shakespeare Circle
Rockport Oak Knoll - Shakespeare Circle $119.95 Rated: 5 stars!
View More Like This Cole Haan - Grant Canoe Penny
Cole Haan Grant Canoe Penny $170.00 Rated: 3 stars!
View More Like This Rockport - Oak Knoll - Shakespeare Circle
Rockport Oak Knoll - Shakespeare Circle $119.95 Rated: 5 stars!
View More Like This ECCO - Holton Penny Loafer
ECCO Holton Penny Loafer $180.00

View More Like This Cole Haan - Pinch Weekender Textile
Cole Haan Pinch Weekender Textile $90.00 $72.99 Rated: 5 stars!
View More Like This Born - Andes
Born Andes $100.00
View More Like This To Boot New York - Senato
To Boot New York Senato $325.00 $229.90 Rated: 5 stars!
View More Like This Massimo Matteo - Pitstop Penny Driver
Massimo Matteo Pitstop Penny Driver $59.00 Rated: 5 stars!

View More Like This Cole Haan - Pinch Weekender - Prep Prints
Cole Haan Pinch Weekender - Prep Prints $90.00 $80.99
View More Like This ECCO - Holton Penny Loafer
ECCO Holton Penny Loafer $180.00
View More Like This Massimo Matteo - Pitstop Penny Driver
Massimo Matteo Pitstop Penny Driver $59.00 Rated: 5 stars!
View More Like This Massimo Matteo - Suede Nubuck Penny
Massimo Matteo Suede Nubuck Penny $79.00 Rated: 5 stars!

View More Like This ECCO - Dynamic Moc 2.0
ECCO Dynamic Moc 2.0 $170.00
View More Like This Allen-Edmonds - Lake Forest
Allen-Edmonds Lake Forest $395.00 Rated: 5 stars!
Massimo Matteo - Penny Classic
Massimo Matteo Penny Classic $99.00
NEW!
ALDO - Wiellaford
ALDO Wiellaford $160.00 $144.99

View More Like This Sperry - Hampden Penny
Sperry Hampden Penny $100.00 Rated: 4 stars!
G.H. Bass & Co. - Larson Weejuns
G.H. Bass & Co. Larson Weejuns $109.95 Rated: 5 stars!
View More Like This Florsheim - Jet Penny Slip-On
Florsheim Jet Penny Slip-On $124.95 Rated: 5 stars!
View More Like This Lacoste - Herron 117 1 Cam
Lacoste Herron 117 1 Cam $149.95 $134.99

View More Like This Allen-Edmonds - Cavanaugh
Allen-Edmonds Cavanaugh $275.00 Rated: 3 stars!
View More Like This Massimo Matteo - Suede Nubuck Penny
Massimo Matteo Suede Nubuck Penny $79.00 Rated: 5 stars!
View More Like This SAS - Ace
SAS Ace $165.00
View More Like This Cole Haan - Pinch Weekender
Cole Haan Pinch Weekender $100.00 $69.99 Rated: 4 stars!

View More Like This Cole Haan - Kelson Penny
Cole Haan Kelson Penny $150.00 Rated: 4 stars!
View More Like This Messico - Orozco
Messico Orozco $119.00
View More Like This Massimo Matteo - Saffiano Penny Moc
Massimo Matteo Saffiano Penny Moc $75.00 $67.99 Rated: 4 stars!
View More Like This Cole Haan - Pinch Weekender
Cole Haan Pinch Weekender $100.00 $89.99 Rated: 4 stars!

G.H. Bass & Co. - Larson Weejuns
G.H. Bass & Co. Larson Weejuns $109.95 Rated: 5 stars!
View More Like This Cole Haan - Pinch Grand Penny
Cole Haan Pinch Grand Penny $170.00 Rated: 5 stars!
View More Like This Rockport - Classic Loafer Lite Penny
Rockport Classic Loafer Lite Penny $99.95 Rated: 4 stars!
View More Like This Trask - Sadler
Trask Sadler $195.00 Rated: 4 stars!

View More Like This Johnston & Murphy - Gibson Penny Driver
Johnston & Murphy Gibson Penny Driver $135.00
View More Like This Allen-Edmonds - Sedona
Allen-Edmonds Sedona $195.00
View More Like This Nunn Bush - Noah Beef Roll Penny Slip-On
Nunn Bush Noah Beef Roll Penny Slip-On $85.00 $68.00 Rated: 5 stars!
View More Like This Massimo Matteo - Florencia Penny Driver
Massimo Matteo Florencia Penny Driver $59.00 $47.99 Rated: 3 stars!

View More Like This Dr. Martens - Penton Bar Loafer
Dr. Martens Penton Bar Loafer $130.00 Rated: 5 stars!
View More Like This Salvatore Ferragamo - Muller Loafer
Salvatore Ferragamo Muller Loafer $560.00 Rated: 5 stars!
LUXURY
View More Like This Rockport - Total Motion Loafer Penny
Rockport Total Motion Loafer Penny $129.95 Rated: 5 stars!
View More Like This Salvatore Ferragamo - Fiorino Loafer
Salvatore Ferragamo Fiorino Loafer $560.00
LUXURY

View More Like This Sebago - Grant
Sebago Grant $114.95 Rated: 5 stars!
View More Like This Lacoste - Herron 117 1 Cam
Lacoste Herron 117 1 Cam $149.95
View More Like This Allen-Edmonds - Cavanaugh
Allen-Edmonds Cavanaugh $275.00 Rated: 3 stars!
View More Like This Donald J Pliner - Vinco5
Donald J Pliner Vinco5 $120.00
NEW!

G.H. Bass & Co. - Larson Weejuns
G.H. Bass & Co. Larson Weejuns $109.95 Rated: 5 stars!
View More Like This Sebago - Legacy Penny
Sebago Legacy Penny $134.95 Rated: 5 stars!
View More Like This Carrucci - Penny Wise
Carrucci Penny Wise $110.00 Rated: 5 stars!
View More Like This Clarks - Reazor Drive
Clarks Reazor Drive $120.00