Nearly 60 Years Ago, a Socialite Dressed Her Friends Like Peacocks and Altered Fashion History

Lilly Pulitzer's simple shift finds favor beyond country clubbers

For nearly six decades, Lilly Pulitzer has defined summertime attire for affluent women.
Courtesy of Lilly Pulitzer

As a New Yorker transplanted from Texas, Sarah Bray has resigned herself to a fact of fashion life here: You wear black. Everyone does, the joke goes, though the joke is largely true. But when Bray leaves the city to visit her sorority sisters from Southern Methodist University, or heads down to Palm Beach, Fla., the dictates of dress change radically. Out goes the black, and in comes the lime green, the peach, the coral and the turquoise.

In other words, on goes the Lilly Pulitzer.

The Secret: Because making a knockoff Lilly dress isn’t especially difficult, the brand hides a tiny “Lilly” signature somewhere in the pattern on each dress. The Pattern: Originally intended to hide juice stains, Pulitzer’s jubilant patterns became hallmarks of summer, of leisure and, in the eyes of many, of a life of privilege. The Style: Relentlessly informal, the Lilly shift dress (named for the 1950s shift to youth culture) has no collar or sleeves, and hangs loose enough to be comfortable.
Courtesy of Lilly Pulitzer

“My sorority sisters are serious Lilly Pulitzer addicts,” said Bray, a style writer for Town & Country. “I was in Palm Beach between Christmas and New Year’s,” she added, “and everyone at the Breakers was wearing Lilly Pulitzer.”

Which shouldn’t surprise. For nearly six decades, Lilly Pulitzer—in particular, its shift dress—has defined summertime attire for affluent women. And while the allure of Lilly is obviously all of those jubilant pastel patterns, a stronger appeal is rooted in legend—that is to say, in Lilly herself.

Courtesy of Lilly Pulitzer

In 1959, following her doctor’s advice to find a hobby, socialite Lilly Pulitzer opened a fruit juice stand in Palm Beach. Instead of donning an apron to catch the orange and grapefruit stains, Pulitzer went to Woolworths, bought some colorful print fabric, and had her seamstress sew a shift dress from it. Pulitzer not only wore the flashy thing, she began selling her design (price: $22 each) at her stand. When the dresses sold better than the juice, a business was born.

Palm Beach socialite Lilly Pulitzer (above, in her first shop) wore her self-designed shifts to cover up juice stains. But her maritime-themed, variegated patterns turned into a fashion movement that drew customers like Jackie Kennedy (inset) and, in time, grew to include an entire fashion line and stores whose interiors (r.) are as splashy as the clothes.
Pulitzer: Courtesy of Lilly Pulitzer; Kennedy: John McInnis Auctioneers

Without quite intending to, Pulitzer had shattered the prevailing white-glove social norms of her class. Her shift dresses (simple, sleeveless, collarless) weren’t just comfortable to wear; their exuberant colors signified a new era of unconventionality and independence—an idea appealing enough to win Jackie Kennedy as an early customer. Kennedy’s dress “was made from kitchen curtain material,” Pulitzer later said, “and people went crazy.”

Two generations later, women are still going crazy for Lilly, though it’s fair to ask: Which women? As was clear from the brand’s 2015 capsule collection for Target (see sidebar), there’s strong demand for the clothes outside the country club set. At the same time, it’s those clubby trappings that make some uncomfortable. As Washington Post fashion critic Robin Givhan has put it: “Lilly Pulitzer suggests an advantage of birth.”

In April 2015, Lilly Pulitzer joined the likes of Jean Paul Gaultier and Missoni, creating a lower-priced collection for Target. Demand was huge, but that was also the trouble: The merch sold out in minutes online and in stores, and thousands were disappointed. Even so, the mess was proof that Lilly’s appeal was no longer limited to the Palm Beach social set.

Perhaps that’s unavoidable for a brand that was, after all, started by an heiress and worn by her friends. Still, a peek at the brand’s Instagram feed—a tableau of photos submitted by fans—makes clear that the demographics of Lilly are no longer just the yachting crowd. And to hear CEO Michelle Kelly explain it, the enduring appeal of the brand isn’t about money, but the connection to a pioneering founder who was ahead of her time. “Lilly Pulitzer still resonates today,” Kelly said, “because of that strong emotional connection, our authentic history that started in Palm Beach, and the optimism and confidence that wearing a Lilly provides.”

This story first appeared in the June 5, 2017, issue of Adweek magazine. Click here to subscribe.