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Men's Shoes

MEN'S SHOP

The timeless penny loafer. Men's loafers and slip-ons from To Boot New York and more.

Complete your look in style and comfort with finely crafted loafers by To Boot New York and more.

SHOP: LOAFERS & SLIP-ONS

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Shoes

1901 'Monroe' Sneaker (Men)
1901 'Monroe' Sneaker (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 'Vartan' Leather Sneaker (Men)
Cole Haan 'Vartan' Leather Sneaker (Men)
1901 'Monroe' Sneaker (Men)
1901 'Monroe' Sneaker (Men)
ECCO 'Chander' Sneaker (Men)
ECCO 'Chander' Sneaker (Men)
ECCO 'Chander' Sneaker (Men)Was: $149.95Now: $99.9033% OFF
Cole Haan 'Air Madison' Wingtip
Cole Haan 'Air Madison' Wingtip
ECCO 'Chander' Sneaker (Men)
ECCO 'Chander' Sneaker (Men)
ECCO 'Chander' Sneaker (Men)Was: $149.95Now: $99.9033% OFF
Cole Haan 'Air Aiden' Penny Loafer
Cole Haan 'Air Aiden' Penny Loafer
ECCO 'Eisner' Sneaker (Men)
ECCO 'Eisner' Sneaker (Men)
Wolverine '1000 Mile - Centennial' Round Toe Boot (Men)
Wolverine '1000 Mile - Centennial' Round Toe Boot (Men)
New MarkdownWolverine '1000 Mile - Centennial' Round Toe Boot (Men)Was: $400.00Now: $259.9035% OFF
Red Wing Moc Toe Boot (Men)
Red Wing Moc Toe Boot (Men)
John Varvatos Star USA 'Hipster' Chukka Boot (Men)
John Varvatos Star USA 'Hipster' Chukka Boot (Men)
John Varvatos Star USA 'Hipster' Chukka Boot (Men)
John Varvatos Star USA 'Hipster' Chukka Boot (Men)
Cole Haan 'Air Madison' Wingtip
Cole Haan 'Air Madison' Wingtip
ECCO 'Seattle' Bike Toe Oxford (Men)
ECCO 'Seattle' Bike Toe Oxford (Men)
G.H. Bass & Co. 'Buckingham' Buck Shoe
G.H. Bass & Co. 'Buckingham' Buck Shoe
Sebago 'Brattle' Wingtip Oxford (Online Only)
Sebago 'Brattle' Wingtip Oxford (Online Only)
Nike 'Free Trainer 3.0' Training Shoe (Men)
Nike 'Free Trainer 3.0' Training Shoe (Men)
Price MatchedNike 'Free Trainer 3.0' Training Shoe (Men)Was: $110.00Now: $89.9715% OFF
Nike 'Free 4.0 Flyknit' Running Shoe (Men)
Nike 'Free 4.0 Flyknit' Running Shoe (Men)
Price MatchedNike 'Free 4.0 Flyknit' Running Shoe (Men)Was: $120.00Now: $99.9715% OFF
Sperry Top-Sider® 'Gold Cup - Authentic Original' Boat Shoe (Men)
Sperry Top-Sider® 'Gold Cup - Authentic Original' Boat Shoe (Men)
Sperry Top-Sider® 'Authentic Original' Boat Shoe (Men)
Sperry Top-Sider® 'Authentic Original' Boat Shoe (Men)
Birkenstock 'Monterey' Leather Slide Sandal (Men)
Birkenstock 'Monterey' Leather Slide Sandal (Men)
Prada 'Saffiano' Penny Driving Shoe
Prada 'Saffiano' Penny Driving Shoe
New MarkdownPrada 'Saffiano' Penny Driving ShoeWas: $650.00Now: $389.9840% OFF
Deer Stags 'Nordic' Slipper (Men)
Deer Stags 'Nordic' Slipper (Men)
Converse 'Jack Purcell - Jack' Sneaker (Men)
Converse 'Jack Purcell - Jack' Sneaker (Men)
Cole Haan 'Vartan' Leather Sneaker (Men)
Cole Haan 'Vartan' Leather Sneaker (Men)