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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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To Boot New York 'Moore' Penny Loafer (Men)
To Boot New York 'Moore' Penny Loafer (Men)
Donald J Pliner 'Broy' Venetian Slip-On (Men)
Donald J Pliner 'Broy' Venetian Slip-On (Men)
Donald J Pliner 'Broy' Venetian Slip-On (Men)Was: $230.00Now: $149.9035% OFF
Cole Haan 'Air Aiden' Penny Loafer
Cole Haan 'Air Aiden' Penny Loafer
ECCO 'New Jersey' Slip-On
ECCO 'New Jersey' Slip-On
New MarkdownECCO 'New Jersey' Slip-OnWas: $159.95Now: $109.9030% OFF
Rated 4.6 out of 5 stars with(22) reviews
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)
Salvatore Ferragamo 'Navarro' Bit Loafer (Men)
Salvatore Ferragamo 'Navarro' Bit Loafer (Men)
TOMS 'Sabados' Canvas Slip-On (Men)
TOMS 'Sabados' Canvas Slip-On (Men)
Cole Haan 'Santa Barbara' Leather Loafer (Men)
Cole Haan 'Santa Barbara' Leather Loafer (Men)
Magnanni 'Lino' Loafer
Magnanni 'Lino' Loafer
New MarkdownMagnanni 'Lino' LoaferWas: $295.00 - $299.00Now: $199.9030% OFF
Rated 4.6 out of 5 stars with(8) reviews
Bruno Magli 'Raging' Loafer (Men)
Bruno Magli 'Raging' Loafer (Men)
Cole Haan 'Pinch' Tassel Loafer (Men)
Cole Haan 'Pinch' Tassel Loafer (Men)
Cole Haan 'Howland' Penny Loafer (Men)
Cole Haan 'Howland' Penny Loafer   (Men)
Gordon Rush 'Adrian' Slip-On
Gordon Rush 'Adrian' Slip-On
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
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
Clarks® 'Senner Lane' Slip-On (Men)
Clarks® 'Senner Lane' Slip-On   (Men)
To Boot New York 'Erik' Venetian Loafer
To Boot New York 'Erik' Venetian 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
Cole Haan 'Lenox Hill' Venetian Loafer (Men)
Cole Haan 'Lenox Hill' Venetian Loafer (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)
BOSS HUGO BOSS 'Varmons' Apron Toe Loafer (Men)
BOSS HUGO BOSS 'Varmons' Apron Toe Loafer (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
Kenneth Cole New York 'Reign or Shine' Driving Shoe (Men)
Kenneth Cole New York 'Reign or Shine' Driving Shoe (Men)
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
Bruno Magli 'Raging' Venetian Loafer (Men) (Online Only)
Bruno Magli 'Raging' Venetian Loafer (Men) (Online Only)
Kenneth Cole New York 'Stick with Me' Penny Loafer (Men)
Kenneth Cole New York 'Stick with Me' Penny Loafer (Men)
New MarkdownKenneth Cole New York 'Stick with Me' Penny Loafer (Men)Was: $168.00Now: $112.5633% OFF
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
ECCO 'Hybrid' Suede Driving Shoe (Men)
ECCO 'Hybrid' Suede Driving Shoe (Men)
ECCO 'Hybrid' Suede Driving Shoe (Men)Was: $159.95Now: $119.9025% OFF
Santoni 'Tristan' Penny Loafer (Men)
Santoni 'Tristan' Penny Loafer (Men)
Santoni 'Tristan' Penny Loafer (Men)Was: $725.00Now: $485.7533% OFF
Mezlan 'Fabriano' Venetian Loafer (Men)
Mezlan 'Fabriano' Venetian Loafer (Men)
New MarkdownMezlan 'Fabriano' Venetian Loafer (Men)Was: $395.00Now: $256.7535% OFF
Sperry Top-Sider® 'Gold Cup - Bellingham' Penny Loafer
Sperry Top-Sider® 'Gold Cup - Bellingham' Penny Loafer
New MarkdownSperry Top-Sider® 'Gold Cup - Bellingham' Penny LoaferWas: $180.00Now: $119.9033% OFF
Cole Haan 'Grant' Driving Shoe (Men)
Cole Haan 'Grant' Driving Shoe   (Men)
Kenneth Cole Reaction 'Key Note' Slip-On
Kenneth Cole Reaction 'Key Note' Slip-On
Prada 'Toblac' Suede Penny Loafer
Prada 'Toblac' Suede Penny Loafer
Donald J Pliner 'Rex' Loafer
Donald J Pliner 'Rex' Loafer
Price MatchedDonald J Pliner 'Rex' LoaferWas: $250.00Now: $225.0010% OFF
Kenneth Cole New York 'Pop the Cork' Venetian Loafer (Men)
Kenneth Cole New York 'Pop the Cork' Venetian Loafer (Men)
New MarkdownKenneth Cole New York 'Pop the Cork' Venetian Loafer (Men)Was: $158.00Now: $105.8633% OFF
Kenneth Cole New York 'Wave Hello' Driving Shoe (Men)
Kenneth Cole New York 'Wave Hello' Driving Shoe (Men)
Kenneth Cole New York 'Bling-Able' Venetian Loafer (Men)
Kenneth Cole New York 'Bling-Able' Venetian Loafer (Men)
New MarkdownKenneth Cole New York 'Bling-Able' Venetian Loafer (Men)Was: $158.00Now: $105.8633% OFF
Kenneth Cole New York 'Listen In' Driving Shoe (Men)
Kenneth Cole New York 'Listen In' Driving Shoe (Men)
New MarkdownKenneth Cole New York 'Listen In' Driving Shoe (Men)Was: $138.00Now: $92.4633% OFF
Cole Haan 'Centre Street' Venetian Loafer (Men)
Cole Haan 'Centre Street' Venetian Loafer (Men)
Donald J Pliner 'Zanda' Canvas Double Monk Strap Shoe (Men)
Donald J Pliner 'Zanda' Canvas Double Monk Strap Shoe (Men)
Price MatchedDonald J Pliner 'Zanda' Canvas Double Monk Strap Shoe (Men)Was: $245.00Now: $225.005% OFF
Ted Baker London 'Fotiu' Leather Loafer (Men)
Ted Baker London 'Fotiu' Leather Loafer (Men)
Ted Baker London 'Fotiu' Leather Loafer (Men)Was: $185.00Now: $149.9015% OFF
Andrew Marc 'Metropolis' Leather Driving Shoe (Men)
Andrew Marc 'Metropolis' Leather Driving Shoe (Men)
Andrew Marc 'Empire' Suede Driving Shoe (Men)
Andrew Marc 'Empire' Suede Driving Shoe (Men)
New MarkdownAndrew Marc 'Empire' Suede Driving Shoe (Men)Was: $178.00Now: $114.9035% OFF
Mezlan 'Arezzo' Loafer (Men)
Mezlan 'Arezzo' Loafer (Men)
New MarkdownMezlan 'Arezzo' Loafer (Men)Was: $355.00Now: $230.7535% OFF
Sperry 'Essex' Penny Loafer (Men)
Sperry 'Essex' Penny Loafer (Men)
Price MatchedSperry 'Essex' Penny Loafer (Men)Was: $125.00Now: $97.9820% OFF
Bacco Bucci 'Ariston' Venetian Loafer (Men)
Bacco Bucci 'Ariston' Venetian Loafer (Men)
New MarkdownBacco Bucci 'Ariston' Venetian Loafer (Men)Was: $215.00Now: $138.9035% OFF
Gordon Rush 'Harden' Venetian Slip-On (Men)
Gordon Rush 'Harden' Venetian Slip-On (Men)
New MarkdownGordon Rush 'Harden' Venetian Slip-On (Men)Was: $195.00Now: $129.9033% OFF
Mezlan 'Clovet' Loafer (Men)
Mezlan 'Clovet' Loafer (Men)
New MarkdownMezlan 'Clovet' Loafer (Men)Was: $495.00Now: $346.5030% OFF
ECCO 'Dublin' Venetian Loafer (Men)
ECCO 'Dublin' Venetian Loafer (Men)
Mezlan 'Pujol' Venetian Loafer (Men)
Mezlan 'Pujol' Venetian Loafer (Men)
New MarkdownMezlan 'Pujol' Venetian Loafer (Men)Was: $295.00Now: $191.7535% OFF
Anatomic & Co 'Barbosa' Penny Loafer (Men)
Anatomic & Co 'Barbosa' Penny Loafer (Men)
New MarkdownAnatomic & Co 'Barbosa' Penny Loafer (Men)Was: $160.00Now: $99.9035% OFF
Mezlan 'Eugenio' Penny Loafer (Men)
Mezlan 'Eugenio' Penny Loafer (Men)
New MarkdownMezlan 'Eugenio' Penny Loafer (Men)Was: $395.00Now: $256.7535% OFF
Donald J Pliner 'Rex' Loafer
Donald J Pliner 'Rex' Loafer
Bacco Bucci 'Bartalli' Slip-On (Men)
Bacco Bucci 'Bartalli' Slip-On (Men)
New MarkdownBacco Bucci 'Bartalli' Slip-On (Men)Was: $255.00Now: $164.9035% OFF
Cole Haan 'Dwight' Loafer (Men)
Cole Haan 'Dwight' Loafer   (Men)
BOSS 'Mellion' Patent Loafer (Men)
BOSS 'Mellion' Patent Loafer (Men)
Cole Haan 'Pinch Buckle' Loafer (Men)
Cole Haan 'Pinch Buckle' Loafer   (Men)
G Brown 'Capri' Suede Driving Shoe (Men)
G Brown 'Capri' Suede Driving Shoe (Men)
New MarkdownG Brown 'Capri' Suede Driving Shoe (Men)Was: $170.00Now: $99.9040% OFF
Donald J Pliner 'Dacio II' Loafer
Donald J Pliner 'Dacio II' Loafer
Neil M 'Cape' Slip-On
Neil M 'Cape' Slip-On
Clarks® 'Allston Free' Leather Slip-On (Men)
Clarks® 'Allston Free' Leather Slip-On (Men)
Price MatchedClarks® 'Allston Free' Leather Slip-On (Men)Was: $89.95Now: $59.9033% OFF
Steve Madden 'Winlock' Leather Bit Loafer (Men)
Steve Madden 'Winlock' Leather Bit Loafer (Men)
Price MatchedSteve Madden 'Winlock' Leather Bit Loafer (Men)Was: $115.00Now: $86.2525% OFF
Steve Madden 'Genesee' Leather Slip-On (Men)
Steve Madden 'Genesee' Leather Slip-On (Men)
Price MatchedSteve Madden 'Genesee' Leather Slip-On (Men)Was: $99.95Now: $79.9920% OFF
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
Sperry 'Essex' Loafer (Men)
Sperry 'Essex' Loafer (Men)
Sperry 'Essex' Loafer (Men)Was: $125.00Now: $89.9025% OFF
Anatomic & Co 'Parati' Slip-On (Men)
Anatomic & Co 'Parati' Slip-On (Men)
New MarkdownAnatomic & Co 'Parati' Slip-On (Men)Was: $160.00Now: $99.9035% OFF
Kenneth Cole New York 'Stick Out' Bit Loafer (Men)
Kenneth Cole New York 'Stick Out' Bit Loafer (Men)
Cole Haan 'Santa Barbara' Leather Loafer (Men)
Cole Haan 'Santa Barbara' Leather Loafer (Men)
Cole Haan 'Santa Barbara' Leather Loafer (Men)Was: $158.00Now: $109.0030% OFF
Ted Baker London 'Brently' Camo Suede Driving Shoe (Men)
Ted Baker London 'Brently' Camo Suede Driving Shoe (Men)
Ted Baker London 'Graaem 2' Patent Leather Penny Loafer (Men)
Ted Baker London 'Graaem 2' Patent Leather Penny Loafer (Men)
Cole Haan 'Grant Canoe' Driving Shoe (Men)
Cole Haan 'Grant Canoe' Driving Shoe (Men)
Cole Haan 'Grant Canoe' Driving Shoe (Men)Was: $168.00Now: $79.9750% OFF
Calvin Klein 'Duke' Leather Loafer (Men)
Calvin Klein 'Duke' Leather Loafer (Men)
New MarkdownCalvin Klein 'Duke' Leather Loafer (Men)Was: $150.00Now: $104.9030% OFF
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
Børn 'Harmon' Loafer (Men)
Børn 'Harmon' Loafer (Men)
Price MatchedBørn 'Harmon' Loafer (Men)Was: $98.95Now: $82.2515% OFF
Steve Madden 'Actionn' Canvas Driving Shoe (Men)
Steve Madden 'Actionn' Canvas Driving Shoe (Men)
Price MatchedSteve Madden 'Actionn' Canvas Driving Shoe (Men)Was: $89.95Now: $52.9840% OFF
Cole Haan 'Dalton' Moc Toe Loafer (Men)
Cole Haan 'Dalton' Moc Toe Loafer   (Men)
Calvin Klein 'Danby' Leather Loafer (Men)
Calvin Klein 'Danby' Leather Loafer (Men)
New MarkdownCalvin Klein 'Danby' Leather Loafer (Men)Was: $150.00Now: $104.9030% OFF
Clarks® 'Mego' Perforated Leather Slip-On (Men)
Clarks® 'Mego' Perforated Leather Slip-On (Men)
New MarkdownClarks® 'Mego' Perforated Leather Slip-On (Men)Was: $99.95Now: $62.9035% OFF
Florsheim 'Fluent' Venetian Loafer
Florsheim 'Fluent' Venetian Loafer
Florsheim 'Fluent' Venetian LoaferWas: $110.00Now: $54.9050% OFF
ECCO 'Dacono' Venetian Loafer (Men)
ECCO 'Dacono' Venetian Loafer (Men)
ECCO 'Dacono' Venetian Loafer (Men)Was: $219.95Now: $159.9025% OFF
Cole Haan 'Pinch Buckle' Loafer (Men)
Cole Haan 'Pinch Buckle' Loafer   (Men)
Price MatchedCole Haan 'Pinch Buckle' Loafer (Men)Was: $158.00Now: $109.9030% OFF

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