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Sperry Top-Sider
2-eye Boat Shoes - Brown
C$160 C$121 (20% off)
Standout
Sperry Top-Sider
Black Boat Loafer Shoes
C$259 C$89 (65% off)
Blue & Cream
Sperry Top-Sider
Billfish 3-eye Boat Shoe - Blue
C$130 C$52 (60% off)
Nordstrom Rack
Sperry Top-Sider
Bow Slip-on Boat Shoes - Grey
C$109 C$46 (55% off)
Saks OFF 5TH
Sperry Top-Sider
Sojourn Nubuck Boat Shoe - Blue
C$130 C$52 (60% off)
Nordstrom Rack
Sperry Top-Sider
Monterey Penny Loafer - Brown
C$104 C$52 (50% off)
Nordstrom Rack

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Since its inception in 1935, American label Sperry Top-Sider has become a world-renowned name in preppy, nautical fashion and footwear. The brand was born when founder Paul Sperry sliced into the sides of his rubber sneakers, hoping to replicate the traction his dog's paws had on a slippery boat deck. Since then, the original shoe design has been coveted alongside collections of outerwear, apparel and fashion accessories. Look to the latest men's Sperry Top-Sider slip-on shoes for cool, modern versions of that original boat shoe. Expect vibrant colour combinations, unconventional shapes and designs, bringing a contemporary twist to the timeless footwear favourite.