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Whether you call them A/Os, boat shoes or Top-Siders, they will always be the Originals. Since 1935, these shoes have been the staple for those with a passion for the sea. The A/O combines classic comfort and enduring style for a timeless look. Fashion fades, but style is forever.
Shop the latest and hottest styles from Steve Madden, Sam Edelman, Nine West, French Connection and many more! heel boy offers something for everyone whether it be a hot date, snowy afternoon in the park or a rainy early morning, girls (or boys) night out, power lunch or casual dinner, you can find something for every occasion. Make heel boy your first stop for all that is fabulous in footwear! We are committed to making this the best place to buy shoes online. Watch this store for increased selection of styles and brands as the season progresses!
Our founder, Paul Sperry, was born into a family with a long sea-faring tradition. Paul grew up listening to his great-grandfather speak of wild adventures in the South Seas. These tales set the stage for young Paul’s inventive spirit, passion for sailing and curiosity for adventure.
The rough seas, a slippery deck and a struggle for sure footing almost cost Paul Sperry his life; and began his long and ambitious quest for a solution. One day in 1935, after watching his dog dart effortlessly across the ice on a cold Connecticut day, he was inspired to carved grooves – like those on his dog's paws – into the bottom of a rubber sole. In that moment of inspiration, the world's first boat shoe was born.