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How Lilly Pulitzer Outlasted the Preppy Cliché

Long before the brand became synonymous with collegiate pearls and twinsets, its founder was a Palm Beach rebel whose original vision is finally driving the modern prep revival.

There was a time, not so long ago, when Lilly Pulitzer evoked images of sorority girls at Southern colleges wearing pearls and twinsets. Though the heiress behind the eponymous brand was a noted iconoclast, it seemed her legacy, at least over the past several years, belonged to the staid and subdued—the terminally basic. A scion of generational wealth, Pulitzer was part of the American aristocracy and stumbled into the world of fashion almost accidentally—or, perhaps, serendipitously. Though her name evokes whimsical prints of dancing monkeys and drinking frogs, Lilly Pulitzer’s initial motivations as a dressmaker were strictly practical.

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Born in 1931 to Lillian Bostwick and Robert McKim, Lillian Lee McKim was a Standard Oil heiress who belonged to the rarified world of the East Coast elite, splitting time between family estates in Newport and Long Island and attending Chapin in New York City and then Miss Porter’s School in Connecticut, alongside Jacqueline Kennedy Onassis (then Jacqueline Bouvier). The future first lady would later be instrumental in publicizing the Lilly brand, but despite sartorial similarities, the former classmates differed greatly in public appearances and decorum. While Kennedy Onassis was famously reserved and fastidious, Pulitzer was free-spirited and always more of a wild card: she eloped with publishing scion Peter Pulitzer at the age of 21, and moved to Florida shortly thereafter.

The choice to live full-time in Florida was considered mildly improper, as members of high society were meant to winter in a tropical climate, not reside there year-round. Even more surprising was her decision to forgo a quiet existence as a housewife in favor of opening up a small juice stand in town,........

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