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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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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
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
ECCO 'Soft' Driving Shoe (Men)
ECCO 'Soft' Driving Shoe (Men)
To Boot New York 'Brooklyn' Double Monk Strap Shoe (Men)
To Boot New York 'Brooklyn' Double Monk Strap Shoe (Men)
Sanuk 'Baseline' Slip-On (Men)
Sanuk 'Baseline' Slip-On (Men)
Salvatore Ferragamo 'Navarro' Bit Loafer (Men)
Salvatore Ferragamo 'Navarro' Bit Loafer (Men)
Cole Haan 'Santa Barbara' Leather Loafer (Men)
Cole Haan 'Santa Barbara' Leather Loafer (Men)
Gordon Rush 'Adrian' Slip-On
Gordon Rush 'Adrian' Slip-On
Cole Haan 'Pinch' Tassel Loafer (Men)
Cole Haan 'Pinch' Tassel Loafer (Men)
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 'Parigi' Moccasin
Salvatore Ferragamo 'Parigi' Moccasin
Price MatchedSalvatore Ferragamo 'Parigi' MoccasinWas: $580.00Now: $406.0030% OFF
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
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
Gucci 'Roos' Bit Loafer (Men)
Gucci 'Roos' Bit Loafer (Men)
New MarkdownGucci 'Roos' Bit Loafer (Men)Was: $680.00Now: $407.9840% 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
Tod's 'Laccetto' Driving Shoe
Tod's 'Laccetto' Driving Shoe
New MarkdownTod's 'Laccetto' Driving ShoeWas: $525.00Now: $351.7533% OFF
To Boot New York 'Erik' Venetian Loafer
To Boot New York 'Erik' Venetian Loafer
1901 'Torino' Perforated Driving Shoe (Men)
1901 'Torino' Perforated Driving Shoe (Men)
ECCO 'Seattle' Slip-On (Men)
ECCO 'Seattle' Slip-On (Men)
Santoni 'Vance' Bit Loafer (Men)
Santoni 'Vance' Bit Loafer (Men)
Cole Haan 'Lenox Hill' Venetian Loafer (Men)
Cole Haan 'Lenox Hill' Venetian Loafer (Men)
Cole Haan Pinch Penny Loafer
Cole Haan Pinch Penny Loafer
Salvatore Ferragamo 'Nowell' Leather Driving Shoe (Men)
Salvatore Ferragamo 'Nowell' Leather Driving Shoe (Men)
Kenneth Cole Reaction 'Cross the Desert' Venetian Loafer (Men)
Kenneth Cole Reaction 'Cross the Desert' Venetian Loafer (Men)
Santoni 'Austin' Penny Loafer (Men)
Santoni 'Austin' Penny Loafer (Men)
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
Kenneth Cole New York 'Reign or Shine' Driving Shoe (Men)
Kenneth Cole New York 'Reign or Shine' Driving Shoe (Men)
Magnanni 'Arturo' Double Monk Strap Cap Toe Shoe (Men)
Magnanni 'Arturo' Double Monk Strap Cap Toe Shoe (Men)
New MarkdownMagnanni 'Arturo' Double Monk Strap Cap Toe Shoe (Men)Was: $350.00Now: $219.9035% 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
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
ALDO 'Mopsa' Driving Shoe (Men)
ALDO 'Mopsa' Driving Shoe (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)
Sandro Moscoloni 'Palermo' Leather Bit Loafer (Men)
Sandro Moscoloni 'Palermo' Leather Bit Loafer (Men)
Sandro Moscoloni 'Paris' Leather Penny Loafer (Men)
Sandro Moscoloni 'Paris' Leather Penny Loafer (Men)
Dune London 'Academy' Cap Toe Oxford (Men)
Dune London 'Academy' Cap Toe Oxford (Men)
Salvatore Ferragamo 'Sardegna' Driving Shoe (Men)
Salvatore Ferragamo 'Sardegna' Driving Shoe (Men)
Gucci 'Boss' Monk Strap Shoe (Men)
Gucci 'Boss' Monk Strap Shoe (Men)
Dune London 'Brighton' Woven Loafer (Men)
Dune London 'Brighton' Woven Loafer (Men)
Dune London 'Racehorse' Penny Loafer (Men)
Dune London 'Racehorse' Penny Loafer (Men)
To Boot New York 'Ashton' Driving Shoe
To Boot New York 'Ashton' Driving Shoe
Cole Haan 'Grant Canoe' Penny Loafer (Men)
Cole Haan 'Grant Canoe' Penny Loafer   (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
Sandro Moscoloni 'Porto' Leather Loafer (Men)
Sandro Moscoloni 'Porto' Leather Loafer (Men)
Robert Wayne 'Highway/ Slip-On (Men)
Robert Wayne 'Highway/ Slip-On (Men)
Sandro Moscoloni 'Sicily' Suede Driving Shoe (Men)
Sandro Moscoloni 'Sicily' Suede Driving Shoe (Men)
Dune London 'Brightly' Penny Loafer (Men)
Dune London 'Brightly' Penny Loafer (Men)
Salvatore Ferragamo 'Sardegna 8' Driving Shoe (Men)
Salvatore Ferragamo 'Sardegna 8' Driving Shoe (Men)
Robert Wayne 'Akira' Slip-On Moccasin (Men)
Robert Wayne 'Akira' Slip-On Moccasin (Men)
Sanuk 'Sideline Patriot' Slip-On (Men)
Sanuk 'Sideline Patriot' Slip-On (Men)

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