This year marks Lilly Pulitzer’s 60th anniversary - what started as one Palm Beach socialite’s easy way to avoid juice stains on her dress has become a national fashion institution.
The original range of brightly colored shifts Lilly began making in the early 1960s has now expanded into home goods, athleisure, laptop cases, flip flops, and even bicycles. If you wanted to, you now could live an almost completely Lilly Pulitzer-designed lifestyle - though you'd need to have a penchant for pink.
Over the years Lilly Pulitzer has become the bright antidote to wintery metropolitan greys and blacks, bringing to mind Southern sorority girls sipping sweet tea, socialites with G&Ts firmly in hand on Palm Beach, and of course Jackie Kennedy, who helped make the brand a go-to wardrobe staple for the jet set. Over the years, the Kennedy offspring have continued the tradition of wearing Lilly too.
Influencer Catherine Grace O'Connell grew up in Illinois wearing Lilly, which she calls “timeless and classic.” Grace, an ageism activist on Instagram, still wears Lilly today alongside her daughter.
“I remember choosing the perfect Lilly Pulitzer dress [as a child] before a family trip to Florida. It was filled with beautiful flowers and the prettiest white lace,” she said. She even remembers her adult daughter’s first Lilly, a pink floral shift dress. “It’s a dress she could wear to this day,” she said. “My daughter has been stealing my clothes since she was in high school. The beauty is that we both love Lilly and although there are three decades between us, we would wear the same designs. The power of Lilly is its instant recognition.”
Influencer, socialite, and comedian Renée Willett agrees with the generational outlook, calling it “an iconic brand” that’s a departure from “the usual bland khaki preppy look.”
“Ever since I can remember, I wore Lilly Pulitzer,” she said, explaining that her Mom’s Connecticut lifestyle inspired her. They’d wear the same dresses in the summer, her sporting the miniature version. “It just feels natural to wear Lilly while traveling in St. Barths or at dinner on lovely summer nights at the Glen Oaks Country Club in Old Westbury New York, or attending a beach house party in Palm Beach," she said.
Of course, Lilly isn’t exclusively reserved for the country club set. When they partnered with Target in 2015 the collection sold out immediately.
There were some diehard fans of the brand who objected to the Target collaboration. “It’s always interesting when a quiet company or brand not looking for publicity suddenly gets thrown into the center of the storm and people discover it," Preppy Handbook author Lisa Birnbach (an authority on all things Lilly) told us. But, she added, the Lilly she met “would have been very pleased that her merchandise would be available to a different and more diverse community.”
Birnbach spent time with the real Lilly in 2008 at her Palm Beach home. She met a woman who was “as shocked as anybody that Lilly Pulitzer was meaningful to people.”
“She loved the high and low of life,” Birnbach explained. “She wasn’t thinking about being a businesswoman or fashion designer, she was thinking about making a little frock to wear and then her friends admired it. As she told me once, a lot of the fabrics came from the equivalent of a five and dime. They were cotton, they were bright, but they weren’t hand painted or artisanal," Birnbach said.
The writer first encountered the brand when she was ten and her mother returned from a trip to Palm Beach with a miniature version of the same dress she had bought herself. “Hers was a Lilly, mine was called a Minnie, which was kind of a pun because it was a miniature version and her daughter was named Minnie.”
At the time, the brand felt so exclusive because it was hyper-local. To wear Lilly, she said, you had to "happen to live in one of the few places that happen to be colonized by Lilly Pulitzer." The list started with Palm Beach, and grew to include Lake Placid, Nantucket, and today, anywhere preppy, and everywhere southern.
“The prints were bold, cheerful, bright and silly, with a yellow and orange striped tiger, a giant sunflower with a blue caterpillar crawling along it. They were joyful, and not necessarily appealing to people who didn’t get it. If you didn’t get it, you didn’t get it. If you’re a woman wearing a menswear-inspired suit in 1975, you’re not going to wear Lilly Pulitzer anywhere but the beach club or country club.”
“She helped me make the argument that dressing preppily is a joyful and silly thing to do. And it's easy, because, in my case anyway, I already have ten different color polo shirts. I already have ten different Lilly skirts, I already have the khakis, I don’t have to keep buying stuff," Birnbach said.
Lilly Pulitzer’s latest collaboration is a luxury one. The brand recently teamed up with Gwyneth Paltrow’s Goop on a series of dresses, skirts, and bags with a higher price point than usual. “In a funny way, it’s perfect. The original Gwyneth 1.0 was an Upper East Side girl wearing a Lilly Pulitzer” Birnbach said. But the higher price point might cause some regular buyers to pause. “Preppies can be frugal. I think if she were around Lilly would say that’s ridiculous and so expensive. That’s why the Junior League has its nearly-new shops all over the country," Birnbach said.
Lilly Pulitzer's CEO argues that the brand might have evolved but it's still all inspired by the woman herself. "The brand has evolved over the years but is still quintessentially Lilly," CEO Michelle Kelly explained. "We are proud of our artistry in handpainted, original prints and Lilly custom colors. Quite literally, you can’t find these anywhere else."
And while women often hit the store for occasion ensembles, it's also become a heritage lifestyle brand, with pieces passed down from mothers to daughters. "Women come in [looking for a] colorful dress for a celebration or printed shorts for vacation; while wearing Lilly they create a connection to fond memories, happiness, and warmth."
