Order Anytime, Free Shipping, Free Returns

“penny loafers and Men Shoes” we found 375 items!

Choose a
  • Product Type
to sort results
Cole Haan - Howland Penny Cole Haan Howland Penny $120.00 Rated: 4 stars! Florsheim - Berkley Penny Loafer Florsheim Berkley Penny Loafer $110.00 Rated: 4 stars! Rockport - Oaklawn Park Penny Rockport Oaklawn Park Penny $99.95 Rated: 4 stars! Born - Simon Born Simon $110.00 $99.00 Rated: 4 stars!
Cole Haan - Howland Penny Cole Haan Howland Penny $120.00 Rated: 4 stars! Florsheim - Berkley Penny Loafer Florsheim Berkley Penny Loafer $110.00 Rated: 4 stars! Rockport - Classic Loafer Lite Penny Rockport Classic Loafer Lite Penny $100.00 Rated: 4 stars! Sebago - Sloop Sebago Sloop $125.00 Rated: 5 stars!
Rockport - Classic Loafer Lite Penny Rockport Classic Loafer Lite Penny $100.00 Rated: 4 stars! Rockport - Classic Loafer Lite Penny Rockport Classic Loafer Lite Penny $100.00 Rated: 4 stars! Nunn Bush - Lincoln Penny Loafer Nunn Bush Lincoln Penny Loafer $80.00 $64.00 Rated: 4 stars! Rockport - Oaklawn Park Penny Rockport Oaklawn Park Penny $99.95 Rated: 4 stars!
Nunn Bush - Lincoln Penny Loafer Nunn Bush Lincoln Penny Loafer $80.00 $64.00 Rated: 4 stars! Massimo Matteo - Saffiano Penny Moc Massimo Matteo Saffiano Penny Moc $75.00 Rated: 4 stars! Cole Haan - Pinch Weekender Cole Haan Pinch Weekender $90.00 Rated: 5 stars! Rockport - Oak Knoll - Shakespeare Circle Rockport Oak Knoll - Shakespeare Circle $119.95 Rated: 5 stars!
Florsheim - Jet Penny Slip-On Florsheim Jet Penny Slip-On $125.00 Rated: 4 stars! Florsheim - Cricket Penny Florsheim Cricket Penny $100.00 Rated: 4 stars! Allen-Edmonds - Daytona Allen-Edmonds Daytona $195.00 Rated: 5 stars! ECCO - Classic Moc 2.0 Loafer ECCO Classic Moc 2.0 Loafer $150.00 Rated: 5 stars!
Cole Haan - Pinch Weekender Cole Haan Pinch Weekender $90.00 Rated: 5 stars! Cole Haan - Pinch Weekender Cole Haan Pinch Weekender $78.00 Rated: 5 stars! Nunn Bush - Appleton Moc Toe Penny Loafer Nunn Bush Appleton Moc Toe Penny Loafer $85.00 $68.00 Rated: 5 stars! Johnston & Murphy - Ainsworth Penny Johnston & Murphy Ainsworth Penny $145.00 Rated: 4 stars!
Florsheim - Jasper Penny Loafer Slip-On Florsheim Jasper Penny Loafer Slip-On $110.00 Rated: 5 stars! Cole Haan - Pinch Weekender Cole Haan Pinch Weekender $100.00 Rated: 5 stars! ECCO - Classic Moc 2.0 Loafer ECCO Classic Moc 2.0 Loafer $150.00 Rated: 5 stars! Cole Haan - Pinch Weekender Cole Haan Pinch Weekender $90.00 Rated: 5 stars!
Rockport - Oak Knoll - Shakespeare Circle Rockport Oak Knoll - Shakespeare Circle $119.95 Rated: 5 stars! Florsheim - Jasper Penny Loafer Slip-On Florsheim Jasper Penny Loafer Slip-On $110.00 Rated: 5 stars! Salvatore Ferragamo - Rocco Loafer Salvatore Ferragamo Rocco Loafer $560.00 Giorgio Brutini - Tonik Giorgio Brutini Tonik $69.00
Cole Haan - Pinch Weekender Cole Haan Pinch Weekender $100.00 Rated: 5 stars! ECCO - Classic Moc 2.0 Loafer ECCO Classic Moc 2.0 Loafer $150.00 Rated: 5 stars! Cole Haan - Pinch Buckle Cole Haan Pinch Buckle $99.00 Rated: 4 stars! Stacy Adams - Roswell Stacy Adams Roswell $90.00 Rated: 5 stars!
Cole Haan - Pinch Campus Penny Cole Haan Pinch Campus Penny $160.00 Rated: 3 stars! Cole Haan - Kelson Penny Cole Haan Kelson Penny $150.00 Johnston & Murphy - Ainsworth Penny Johnston & Murphy Ainsworth Penny $145.00 Rated: 4 stars! Cole Haan - Grant Canoe Penny Cole Haan Grant Canoe Penny $170.00 Rated: 3 stars!
Cole Haan - Pinch Weekender Cole Haan Pinch Weekender $90.00 Rated: 5 stars! Massimo Matteo - Saffiano Penny Moc Massimo Matteo Saffiano Penny Moc $75.00 Rated: 4 stars! Cole Haan - Pinch Weekender Cole Haan Pinch Weekender $90.00 Rated: 5 stars! Kenneth Cole Reaction - West Village Kenneth Cole Reaction West Village $135.00 Rated: 5 stars!
Nunn Bush - Appleton Moc Toe Penny Loafer Nunn Bush Appleton Moc Toe Penny Loafer $85.00 $68.00 Rated: 5 stars! Sebago - Classic Sebago Classic $140.00 Rated: 4 stars! Cole Haan - Pinch Penny Cole Haan Pinch Penny $110.00 Rated: 4 stars! Salvatore Ferragamo - Rocco Loafer Salvatore Ferragamo Rocco Loafer $560.00 $447.99
Dockers - Dalton Dockers Dalton $85.00 $59.99 ECCO - Classic Moc 2.0 Loafer ECCO Classic Moc 2.0 Loafer $150.00 Rated: 5 stars! Massimo Matteo - Saffiano Penny Moc Massimo Matteo Saffiano Penny Moc $75.00 Rated: 4 stars! Florsheim - Jet Penny Slip-On Florsheim Jet Penny Slip-On $125.00 Rated: 4 stars!
To Boot New York - Ashton To Boot New York Ashton $295.00 Rated: 5 stars! Cole Haan - Pinch Grand Penny Cole Haan Pinch Grand Penny $170.00 Rated: 5 stars! OluKai - 'Iwa OluKai 'Iwa $160.00 $144.99 Rated: 5 stars! Cole Haan - Pinch Campus Penny Cole Haan Pinch Campus Penny $140.00 Rated: 3 stars!
Salvatore Ferragamo - Muller Loafer Salvatore Ferragamo Muller Loafer $560.00 Rated: 5 stars! To Boot New York - Senato To Boot New York Senato $325.00 Rated: 5 stars! Sebago - Grant Sebago Grant $110.00 Rated: 5 stars! Nunn Bush - Glenwood Slip-On Dress Casual Nunn Bush Glenwood Slip-On Dress Casual $85.00 $68.00 Rated: 4 stars!
Born - Simon Born Simon $110.00 $99.00 Rated: 4 stars! Ben Sherman - Parnell Loafer Ben Sherman Parnell Loafer $60.00 Cole Haan - Pinch Weekender Cole Haan Pinch Weekender $90.00 Rated: 5 stars! Giorgio Brutini - Birch Giorgio Brutini Birch $55.00
Donald J Pliner - Vinco4 Donald J Pliner Vinco4 $124.00 Rated: 5 stars! Donald J Pliner - Vinco4 Donald J Pliner Vinco4 $130.00 Rated: 5 stars! Cole Haan - Pinch Grand Penny Cole Haan Pinch Grand Penny $170.00 Rated: 5 stars! Florsheim - Felix Penny Florsheim Felix Penny $115.00 Rated: 5 stars!
Cole Haan - Pinch Weekender Cole Haan Pinch Weekender $90.00 $80.99 Rated: 5 stars! Lacoste - Concours 116 1 Lacoste Concours 116 1 $164.95 Donald J Pliner - Vinco4 Donald J Pliner Vinco4 $130.00 Rated: 5 stars! Frye - Lewis Penny Frye Lewis Penny $178.00 Rated: 3 stars!
Ben Sherman - Parnell Loafer Ben Sherman Parnell Loafer $60.00 Cycleur de Luxe - Forano Cycleur de Luxe Forano $175.00 Giorgio Brutini - Birch Giorgio Brutini Birch $55.00 Polo Ralph Lauren - Wes II Polo Ralph Lauren Wes II $99.00 Rated: 5 stars!
Sebago - Classic Sebago Classic $140.00 Rated: 4 stars! Sperry Top-Sider - Hampden Penny Sperry Top-Sider Hampden Penny $100.00 Rated: 4 stars! UGG - Tucker UGG Tucker $119.95 Rated: 5 stars! Giorgio Brutini - 478852-4 Giorgio Brutini 478852-4 $75.00 $59.99 Rated: 5 stars!
Stacy Adams - Marcellus Stacy Adams Marcellus $90.00 Rated: 5 stars! Cycleur de Luxe - Forano Cycleur de Luxe Forano $175.00 Lacoste - Concours 116 1 Lacoste Concours 116 1 $164.95 NEW! Massimo Matteo - Mocc Split Penny Loafer Massimo Matteo Mocc Split Penny Loafer $169.00
ALDO - Osegod ALDO Osegod $110.00 Cole Haan - Pinch Penny Cole Haan Pinch Penny $110.00 Rated: 4 stars! Nunn Bush - Glenwood Slip-On Dress Casual Nunn Bush Glenwood Slip-On Dress Casual $85.00 $68.00 Rated: 4 stars! Florsheim - Sabato Penny Florsheim Sabato Penny $130.00 Rated: 3 stars!
Allen-Edmonds - Cavanaugh Allen-Edmonds Cavanaugh $275.00 Rated: 3 stars! Ben Sherman - Parnell Loafer Ben Sherman Parnell Loafer $60.00 Cole Haan - Pinch Weekender Cole Haan Pinch Weekender $90.00 Rated: 5 stars! Steve Madden - Zorzi Steve Madden Zorzi $85.00 Rated: 3 stars!
Trask - Sadler Trask Sadler $225.00 NEW! Sebago - Classic Sebago Classic $140.00 Rated: 4 stars! Johnston & Murphy - Beckwith Penny Johnston & Murphy Beckwith Penny $135.00 Rated: 4 stars! Geox - U Xense Mox 7 Geox U Xense Mox 7 $180.00
Frye - Lewis Penny Frye Lewis Penny $178.00 Rated: 3 stars! Geox - U Xense Mox 7 Geox U Xense Mox 7 $180.00 Sebago - Sloop Sebago Sloop $120.00 $107.99 Rated: 5 stars! Nunn Bush - Kent Moc Toe Penny Loafer Nunn Bush Kent Moc Toe Penny Loafer $85.00 $68.00 Rated: 3 stars!
Zappos Family Core Value:

10. Be Humble