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How Sperry got its groove back

After the preppy heyday of the 1980s, the Sperry Top-Sider became decidedly uncool. Now, a new generation of shoppers has discovered the brand and made it hip again.

LEXINGTON — The 1990s were not kind to the Sperry Top-Sider. The iconic boat shoe blazed to the fashion forefront in the early 1980s after gaining fame in “The Official Preppy Handbook.” But by the end of the decade, the shoe had fallen out of favor, much like Wang Chung. But a renaissance began in the late 2000s, when high-profile designers, looking for classic heritage brands, put Top-Siders on the runways, transforming a stodgy staple into an edgy fashion statement.

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