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Men's Loafers & Slip-Ons

The classic penny loafer from To Boot New York.

A timeless investment that's unquestionably cool, whether for work or play.

Men's Loafers & Slip-Ons

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Cole Haan 'Air Aiden' Penny Loafer
Cole Haan 'Air Aiden' Penny Loafer
Kenneth Cole Reaction 'Think Ahead' Loafer (Men)
Kenneth Cole Reaction 'Think Ahead' Loafer (Men)
New MarkdownKenneth Cole Reaction 'Think Ahead' Loafer (Men)Was: $108.00Now: $69.9035% OFF
ECCO 'Soft' Driving Shoe (Men)
ECCO 'Soft' Driving Shoe (Men)
To Boot New York 'Erik' Venetian Loafer
To Boot New York 'Erik' Venetian Loafer
Cole Haan Pinch Penny Loafer
Cole Haan Pinch Penny Loafer
Price MatchedCole Haan Pinch Penny LoaferWas: $158.00Now: $109.9030% OFF
Rated 5 out of 5 stars with(3) reviews
Bruno Magli 'Raging' Loafer (Men)
Bruno Magli 'Raging' Loafer (Men)
TOMS 'Sabados' Canvas Slip-On (Men)
TOMS 'Sabados' Canvas Slip-On (Men)
Salvatore Ferragamo 'Navarro' Bit Loafer (Men)
Salvatore Ferragamo 'Navarro' Bit Loafer (Men)
Magnanni 'Lino' Loafer
Magnanni 'Lino' Loafer
Magnanni 'Lino' LoaferWas: $295.00 - $299.00Now: $199.9030% OFF
Rated 4.6 out of 5 stars with(8) reviews
Cole Haan 'Santa Barbara' Leather Loafer (Men)
Cole Haan 'Santa Barbara' Leather Loafer (Men)
Cole Haan 'Lenox Hill' Venetian Loafer (Men)
Cole Haan 'Lenox Hill' Venetian Loafer (Men)
Bruno Magli 'Raging' Venetian Loafer (Men) (Online Only)
Bruno Magli 'Raging' Venetian Loafer (Men) (Online Only)
Cole Haan 'Pinch' Tassel Loafer (Men)
Cole Haan 'Pinch' Tassel Loafer (Men)
Gordon Rush 'Adrian' Slip-On
Gordon Rush 'Adrian' Slip-On
Cole Haan 'Howland' Penny Loafer (Men)
Cole Haan 'Howland' Penny Loafer   (Men)
UGG® Australia 'Hunley' Leather Moccasin Loafer (Men)
UGG® Australia 'Hunley' Leather Moccasin Loafer (Men)
Salvatore Ferragamo 'Sardegna 6' Driving Shoe (Men)
Salvatore Ferragamo 'Sardegna 6' Driving Shoe (Men)
Price MatchedSalvatore Ferragamo 'Sardegna 6' Driving Shoe (Men)Was: $640.00Now: $384.0040% OFF
Kenneth Cole Reaction 'Cross the Desert' Venetian Loafer (Men)
Kenneth Cole Reaction 'Cross the Desert' Venetian Loafer (Men)
Salvatore Ferragamo 'Parigi' Moccasin
Salvatore Ferragamo 'Parigi' Moccasin
Price MatchedSalvatore Ferragamo 'Parigi' MoccasinWas: $580.00Now: $406.0030% OFF
Santoni 'Austin' Penny Loafer (Men)
Santoni 'Austin' Penny Loafer (Men)
Prada Suede Driving Shoe
Prada Suede Driving Shoe
New MarkdownPrada Suede Driving ShoeWas: $650.00Now: $389.9840% OFF
Rated 5 out of 5 stars with(2) reviews
Salvatore Ferragamo 'Round' Woven Leather Driving Shoe
Salvatore Ferragamo 'Round' Woven Leather Driving Shoe
Price MatchedSalvatore Ferragamo 'Round' Woven Leather Driving ShoeWas: $660.00Now: $495.0025% OFF
Santoni 'Tristan' Penny Loafer (Men)
Santoni 'Tristan' Penny Loafer (Men)
Santoni 'Tristan' Penny Loafer (Men)Was: $725.00Now: $485.7533% OFF
Prada Spazzalato Leather Penny Loafer (Men)
Prada Spazzalato Leather Penny Loafer (Men)
New MarkdownPrada Spazzalato Leather Penny Loafer (Men)Was: $720.00Now: $431.9840% OFF
Ted Baker London 'Treep 2' Slip-On
Ted Baker London 'Treep 2' Slip-On
Ted Baker London 'Treep 2' Slip-OnWas: $140.00Now: $83.9040% OFF
Tod's 'Laccetto' Driving Shoe
Tod's 'Laccetto' Driving Shoe
New MarkdownTod's 'Laccetto' Driving ShoeWas: $525.00Now: $351.7533% OFF
ALDO 'Mopsa' Driving Shoe (Men)
ALDO 'Mopsa' Driving Shoe (Men)
Magnanni 'Rafa' Bit Loafer
Magnanni 'Rafa' Bit Loafer
ECCO 'Seattle' Slip-On (Men)
ECCO 'Seattle' Slip-On (Men)
Santoni 'Vance' Bit Loafer (Men)
Santoni 'Vance' Bit Loafer (Men)
Cole Haan Pinch Penny Loafer
Cole Haan Pinch Penny Loafer
BOSS 'Mellion' Patent Loafer (Men)
BOSS 'Mellion' Patent Loafer (Men)
1901 'Miami' Suede Driving Shoe (Men)
1901 'Miami' Suede Driving Shoe (Men)
New Markdown1901 'Miami' Suede Driving Shoe (Men)Was: $89.95Now: $59.9033% OFF
Salvatore Ferragamo 'Nowell' Leather Driving Shoe (Men)
Salvatore Ferragamo 'Nowell' Leather Driving Shoe (Men)
ECCO 'Dacono' Venetian Loafer (Men)
ECCO 'Dacono' Venetian Loafer (Men)
ECCO 'Dacono' Venetian Loafer (Men)Was: $219.95Now: $159.9025% OFF
Santoni 'Windsor' Double Monk Strap Shoe (Men)
Santoni 'Windsor' Double Monk Strap Shoe (Men)
Cole Haan 'Douglas' Loafer (Online Only) (Men)
Cole Haan 'Douglas' Loafer (Online Only)   (Men)
Gucci 'Damo' Driving Shoe
Gucci 'Damo' Driving Shoe
Gucci 'Roos' Bit Loafer (Men)
Gucci 'Roos' Bit Loafer (Men)
New MarkdownGucci 'Roos' Bit Loafer (Men)Was: $680.00Now: $407.9840% OFF
Magnanni 'Arturo' Double Monk Strap Cap Toe Shoe (Men)
Magnanni 'Arturo' Double Monk Strap Cap Toe Shoe (Men)
Jimmy Choo 'Brogan' Driving Shoe (Men)
Jimmy Choo 'Brogan' Driving Shoe (Men)
New MarkdownJimmy Choo 'Brogan' Driving Shoe (Men)Was: $650.00Now: $389.9840% OFF
Kenneth Cole New York 'Reign or Shine' Driving Shoe (Men)
Kenneth Cole New York 'Reign or Shine' Driving Shoe (Men)
Mezlan 'Fabriano' Venetian Loafer (Men)
Mezlan 'Fabriano' Venetian Loafer (Men)
Mezlan 'Fabriano' Venetian Loafer (Men)Was: $395.00Now: $256.7535% OFF
Tod's 'Gommini' Driving Shoe (Men)
Tod's 'Gommini' Driving Shoe (Men)
New MarkdownTod's 'Gommini' Driving Shoe (Men)Was: $565.00Now: $378.5533% OFF
Prada Driving Shoe (Men)
Prada Driving Shoe (Men)
New MarkdownPrada Driving Shoe (Men)Was: $680.00Now: $407.9840% OFF
Prada 'Toblac' Suede Penny Loafer
Prada 'Toblac' Suede Penny Loafer
Kenneth Cole New York 'Stick with Me' Penny Loafer (Men)
Kenneth Cole New York 'Stick with Me' Penny Loafer (Men)
1901 'Torino' Perforated Driving Shoe (Men)
1901 'Torino' Perforated Driving Shoe (Men)
ECCO 'Dublin' Venetian Loafer (Men)
ECCO 'Dublin' Venetian Loafer (Men)
Sperry Top-Sider® 'Gold Cup - Bellingham' Penny Loafer
Sperry Top-Sider® 'Gold Cup - Bellingham' Penny Loafer
Cole Haan 'Dwight' Loafer (Men)
Cole Haan 'Dwight' Loafer   (Men)
Salvatore Ferragamo 'Magnifico' Loafer
Salvatore Ferragamo 'Magnifico' Loafer
To Boot New York 'Medford' Double Monk Strap Slip-On
To Boot New York 'Medford' Double Monk Strap Slip-On
Sandro Moscoloni 'Paris' Leather Penny Loafer (Men)
Sandro Moscoloni 'Paris' Leather Penny Loafer (Men)
Dune London 'Racehorse' Penny Loafer (Men)
Dune London 'Racehorse' Penny Loafer (Men)
Dune London 'Brighton' Woven Loafer (Men)
Dune London 'Brighton' Woven Loafer (Men)
TOMS 'Classic - Sabados' Slip-On (Men)
TOMS 'Classic - Sabados' Slip-On (Men)
Cole Haan 'Bedford' Penny Loafer (Men)
Cole Haan 'Bedford' Penny Loafer (Men)
Sandro Moscoloni 'Ancona' Leather Bit Loafer (Men)
Sandro Moscoloni 'Ancona' Leather Bit Loafer (Men)
Magnanni 'Marco' Monk Strap Loafer (Men)
Magnanni 'Marco' Monk Strap Loafer (Men)
Donald J Pliner 'Derrik' Leather Driving Shoe (Men)
Donald J Pliner 'Derrik' Leather Driving Shoe (Men)
Price MatchedDonald J Pliner 'Derrik' Leather Driving Shoe (Men)Was: $185.00Now: $89.9550% OFF

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