How Lilly Pulitzer Redefined Palm Beach Style —

The designer’s carefree aesthetic lives on in the birthplace of American resort wear.

It all started in Palm Beach. A young heiress (Lillian Lee McKim) and publishing scion (Peter Pulitzer) eloped, moving to the south Florida town where they owned a few citrus groves. It was the 1950s, and most women were girdled, lifted and cinched; but not Lilly Pulitzer. After having three children and a nervous breakdown, she opened a little juice stand on Via Mizner — wearing sleeveless, loose–fitting dresses sewn up by her dressmaker (to stay cool in the Palm Beach humidity) in brightly coloured, printed fabrics (to hide the juice stains). When she started selling more dresses than juice, she became the Pucci of Palm Beach: an accidental entrepreneur who invented the shift dress, now known simply as a “Lilly.”

Lilly was unconventional in all things. She hated shoes and underwear, lining her dresses with muslin so women could go au naturel. In the ’40s she dropped out of college so she could deliver medical supplies (on horseback) to new mothers in the remote hills of Kentucky. And when she decided to live year–round in the winter retreat of Palm Beach, raising the eyebrows of everyone in her glamorous set, her constant companion became a pet rhesus monkey.

September 1, 2019
Fashion designer Lilly Pulitzer sits in a low armchair surrounded by flowers in a vintage picture.
The rear area of a speedboat with colourful pillows on the seats and an American flag flying, and water behind.
Lilly Pulitzer, 1960   Elizabeth Kuhner
The Lilly Pulitzer x Barton & Gray Hinckley yacht    Sara Kauss

Just like the rule–breaking gal who loved to throw humdinger house parties that went all night, Lilly’s dresses didn’t follow trends. Before the Lilly arrived, Palm Beach resort wear was a sea of predictably nautical colours and sailor styles. Once described as an upside–down beach bucket, her shift dress was the antithesis of the era’s neutral–coloured, confining clothes — a revolutionary silhouette in an era of form–fitting fashion. Wandering down the palm–lined avenues of Palm Beach, it’s easy to see where her colour palette came from: the town is a tropical hallucination of hibiscus and bougainvillea pinks, sun–dappled jungle greens, lemon groves, tangerine corals and turquoise blues. When her school friend, Jackie Kennedy, was photographed for Life magazine in one of her dresses (famously crafted out of fabric for kitchen curtains), it officially cemented the birth of American resort wear.

A woman in a dress shop stands beside a mannequin wearing a shift dress, in the early 1960s.
Lilly in her first shop, circa 1962   Howell Conant and Lilly Pulitzer

This November would have been Lilly’s 88th birthday, and traces of her can still be found all over Palm Beach. Her legacy is in the lush foliage of the Brazilian Court’s tropical courtyard; the elaborately tiled staircases, blooming orchids and stained glass windows of Worth Avenue’s European–style vias and the blue flamingo mural at the Grandview Public Market. It’s in the raucous laughter spilling out of (and cocktails being spilled inside of) Ta–boo late at night, and in the delicious irreverence of wearing a simple cotton shift with fluorescent pink and green pineapples to dinner at Café Boulud. And, maybe most importantly, it’s in the bright, bold prints that give off a positive energy — not unlike Lilly’s own contagious, free–spirited personality.

When you put on a Lilly, it makes you feel something. It’s an excitement, like knowing you’re guaranteed to have a good time. What started out as the preppy girl’s coastal uniform, whether you were vacationing in the Hamptons or Harbour Island, has now become a lifestyle brand. Sixty years ago, Lilly could never have imagined that her signature, carefree, audacious aesthetic would live on in flip–flops, iPhone cases, paddleboards and, yes, even the odd chartered yacht. But as she once said, “It’s always summer somewhere.”

The cover of a book about Lilly Pulitzer, featuring brightly coloured illustrations of flowers.

Lilly Pulitzer book by Assouline

Palm Beach Travel Essentials
Where to stay

An ornate hotel lobby with vaulted ceilings and green chairs and a cream couch, daytime.
Lobby at The Breakers   The Breakers Palm Beach

The Breakers, a palatial hotel inspired by the Villa Medici in Rome, was such a favourite of Lilly’s that its beach bungalows and formal dining room were immortalized in blue and green toile on a limited–edition scarf. A Lilly Pulitzer flagship store is nestled in the heart of the property.

Eat and drink

Truffle ravioli at the CPB @ The Colony The hotel’s on–site restaurant is a feast for the stomach (truffle and ricotta ravioli; confit lamb belly with mint and harissa; roasted cauliflower with curry and coconut) and the eyes (palm tree prints, pink chintz curtains, banana–leaf wallpaper grace of Dorothy Draper's protégé Carleton Varney).

Bloody Marys at Ta–boo Legend has it that the Bloody Mary was invented at this classic watering hole with a pedigreed past (John F. Kennedy, Frank Sinatra and the Duke and Duchess of Windsor, for starters) tucked inside a pink exterior.

What to do

A woman in a brightly coloured shift dress with flower patterns stands next to a bright pink bike. Her face is out of frame.
   The Brazilian Court Hotel

Lilly Pulitzer bike rental at the Brazilian Court The best accessory in town? Hop on a Lilly Pulitzer bike from this historic hotel and zip from the beach (entrances along South Ocean Boulevard between Royal Palm Way and Hammon Avenue) to the Flagler Museum (the private residence of Henry Flagler, railway tycoon and founder of Palm Beach) in style.

Customized dresses at Lilly Pulitzer The Lilly store is on Worth Avenue, the Rodeo Drive of Palm Beach. Customize your own shift dress based on a selection of exclusive prints, or try on clothes in hand–painted dressing rooms. The ultimate Lilly bon vivant touch: the in–store bar.