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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
Clarks® 'Senner Lane' Slip-On (Men)
Clarks® 'Senner Lane' Slip-On   (Men)
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 'Erik' Venetian Loafer
To Boot New York 'Erik' Venetian Loafer
To Boot New York 'Brooklyn' Double Monk Strap Shoe (Men)
To Boot New York 'Brooklyn' Double Monk Strap Shoe (Men)
ECCO 'Seattle' Slip-On (Men)
ECCO 'Seattle' Slip-On (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
TOMS 'Sabados' Canvas Slip-On (Men)
TOMS 'Sabados' Canvas Slip-On (Men)
Salvatore Ferragamo 'Navarro' Bit Loafer (Men)
Salvatore Ferragamo 'Navarro' Bit Loafer (Men)
Bruno Magli 'Raging' Loafer (Men)
Bruno Magli 'Raging' Loafer (Men)
Cole Haan 'Santa Barbara' Leather Loafer (Men)
Cole Haan 'Santa Barbara' Leather Loafer (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)
ECCO 'Dublin' Venetian Loafer (Men)
ECCO 'Dublin' 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)
New MarkdownUGG® Australia 'Hunley' Leather Moccasin Loafer (Men)Was: $99.95Now: $65.9033% 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
Salvatore Ferragamo 'Parigi' Moccasin
Salvatore Ferragamo 'Parigi' Moccasin
Price MatchedSalvatore Ferragamo 'Parigi' MoccasinWas: $580.00Now: $406.0030% OFF
Kenneth Cole Reaction 'Cross the Desert' Venetian Loafer (Men)
Kenneth Cole Reaction 'Cross the Desert' Venetian Loafer (Men)
ECCO 'Dacono' Venetian Loafer (Men)
ECCO 'Dacono' Venetian Loafer (Men)
ECCO 'Dacono' Venetian Loafer (Men)Was: $219.95Now: $159.9025% OFF
Santoni 'Austin' Penny Loafer (Men)
Santoni 'Austin' Penny Loafer (Men)
Cole Haan 'Douglas' Loafer (Online Only) (Men)
Cole Haan 'Douglas' Loafer (Online Only)   (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
BOSS HUGO BOSS 'Varmons' Apron Toe Loafer (Men)
BOSS HUGO BOSS 'Varmons' Apron Toe Loafer (Men)
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
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)
New MarkdownKenneth Cole New York 'Reign or Shine' Driving Shoe (Men)Was: $138.00Now: $92.4633% 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 Spazzalato Leather Penny Loafer (Men)
Prada Spazzalato Leather Penny Loafer (Men)
New MarkdownPrada Spazzalato Leather Penny Loafer (Men)Was: $720.00Now: $431.9840% 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
New MarkdownTed Baker London 'Treep 2' Slip-OnWas: $140.00Now: $83.9040% OFF
Prada 'Toblac' Suede Penny Loafer
Prada 'Toblac' Suede Penny Loafer
Tod's 'Laccetto' Driving Shoe
Tod's 'Laccetto' Driving Shoe
New MarkdownTod's 'Laccetto' Driving ShoeWas: $525.00Now: $351.7533% OFF
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
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
Ted Baker London 'Haari' Leather Plain Toe Oxford (Men)
Ted Baker London 'Haari' Leather Plain Toe Oxford (Men)
New MarkdownTed Baker London 'Haari' Leather Plain Toe Oxford (Men)Was: $220.00Now: $131.9040% 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 'Eugenio' Penny Loafer (Men)
Mezlan 'Eugenio' Penny Loafer (Men)
New MarkdownMezlan 'Eugenio' Penny Loafer (Men)Was: $395.00Now: $256.7535% OFF
Cole Haan 'Dwight' Loafer (Men)
Cole Haan 'Dwight' Loafer   (Men)
Florsheim 'Fluent' Venetian Loafer
Florsheim 'Fluent' Venetian Loafer
Florsheim 'Fluent' Venetian LoaferWas: $110.00Now: $54.9050% OFF
Santoni 'Windsor' Double Monk Strap Shoe (Men)
Santoni 'Windsor' Double Monk Strap Shoe (Men)
Cole Haan 'LunarGrand' Apron Toe Loafer (Men)
Cole Haan 'LunarGrand' Apron Toe Loafer   (Men)
G Brown 'Tobago' Driving Shoe
G Brown 'Tobago' Driving Shoe
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
Gucci 'Hylands' Patent Leather Loafer
Gucci 'Hylands' Patent Leather Loafer
New MarkdownGucci 'Hylands' Patent Leather LoaferWas: $695.00Now: $416.9840% OFF
Mezlan 'Fabriano' Venetian Loafer (Men)
Mezlan 'Fabriano' Venetian Loafer (Men)
New MarkdownMezlan 'Fabriano' Venetian Loafer (Men)Was: $395.00Now: $256.7535% 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
Cole Haan 'Centre Street' Venetian Loafer (Men)
Cole Haan 'Centre Street' Venetian Loafer (Men)
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)
Kenneth Cole New York 'Stick Out' Bit Loafer (Men)
Kenneth Cole New York 'Stick Out' Bit 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
ECCO 'Hybrid' Suede Driving Shoe (Men)
ECCO 'Hybrid' Suede Driving Shoe (Men)
ECCO 'Hybrid' Suede Driving Shoe (Men)Was: $159.95Now: $119.9025% OFF
Donald J Pliner Slip-On Loafer
Donald J Pliner Slip-On Loafer
Cole Haan 'Pinch Tassel' Loafer (Online Only) (Men)
Cole Haan 'Pinch Tassel' Loafer (Online Only)   (Men)
Hush Puppies® 'Circuit' Venetian Loafer
Hush Puppies® 'Circuit' Venetian Loafer
Sebago Classic Penny Loafer (Online Only)
Sebago Classic Penny Loafer (Online Only)
Calvin Klein 'Merl' Suede Driving Shoe (Men)
Calvin Klein 'Merl' Suede Driving Shoe (Men)
New MarkdownCalvin Klein 'Merl' Suede Driving Shoe (Men)Was: $130.00Now: $90.9030% OFF
Cole Haan 'Grant Canoe' Driving Shoe (Men)
Cole Haan 'Grant Canoe' Driving Shoe (Men)
Cole Haan 'Grant Canoe' Driving Shoe (Men)Was: $168.00Now: $109.9035% OFF
Zanzara 'Ruben' Leather Loafer (Men)
Zanzara 'Ruben' Leather Loafer (Men)
Zanzara 'Ruben' Leather Loafer (Men)Was: $195.00Now: $109.9040% OFF
Donald J Pliner 'Rex' Loafer
Donald J Pliner 'Rex' Loafer
Donald J Pliner 'Rex' LoaferWas: $250.00Now: $124.9050% OFF
Santoni 'Tristan' Penny Loafer (Men)
Santoni 'Tristan' Penny Loafer (Men)
New MarkdownSantoni 'Tristan' Penny Loafer (Men)Was: $725.00Now: $485.7533% OFF
Neil M 'Cape' Slip-On
Neil M 'Cape' Slip-On
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 'Wave Hello' Driving Shoe (Men)
Kenneth Cole New York 'Wave Hello' Driving Shoe (Men)
New MarkdownKenneth Cole New York 'Wave Hello' Driving Shoe (Men)Was: $138.00Now: $92.4633% 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 '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
Ted Baker London 'Graaem 2' Patent Leather Penny Loafer (Men)
Ted Baker London 'Graaem 2' Patent Leather Penny Loafer (Men)
New MarkdownTed Baker London 'Graaem 2' Patent Leather Penny Loafer (Men)Was: $240.00Now: $143.9040% 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
Mezlan 'Arezzo' Loafer (Men)
Mezlan 'Arezzo' Loafer (Men)
New MarkdownMezlan 'Arezzo' Loafer (Men)Was: $355.00Now: $230.7535% OFF
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
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
Tommy Bahama 'Finch' Tassel Loafer (Men)
Tommy Bahama 'Finch' Tassel Loafer (Men)
New MarkdownTommy Bahama 'Finch' Tassel Loafer (Men)Was: $225.00Now: $149.9033% OFF
Mezlan 'Clovet' Loafer (Men)
Mezlan 'Clovet' Loafer (Men)
New MarkdownMezlan 'Clovet' Loafer (Men)Was: $495.00Now: $346.5030% OFF
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
Bacco Bucci 'Buffon' Slip-On (Men)
Bacco Bucci 'Buffon' Slip-On (Men)
New MarkdownBacco Bucci 'Buffon' Slip-On (Men)Was: $255.00Now: $164.9035% OFF
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 'Pinch Buckle' Loafer (Men)
Cole Haan 'Pinch Buckle' Loafer   (Men)
G Brown 'Bonaire' Driving Shoe (Men)
G Brown 'Bonaire' Driving Shoe (Men)
New MarkdownG Brown 'Bonaire' Driving Shoe (Men)Was: $175.00Now: $99.9040% OFF
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
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

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