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Exploring Lilly Pulitzer And Her Legacy In South Florida And Beyond

Dine in the lush garden at Café Boulud at the Brazilian Court on Australian Avenue in Palm Beach, and you’re in the midst of Lilly Pulitzer devotees. Dressed in resort wear styles with bright floral prints in sunny hues, it’s a modern-day snapshot of how Pulitzer’s fashion stamp remains iconic and true. In South Florida, the inimitable style of Pulitzer and her trademarked statement-making, “easy dressing” has never lost its appeal or gone out of style.

Lilly Pulitzer had a contagious spirit. Her tenacity, outpouring of creativity and love was as authentic as she, until her death at age 81 in 2013. But even those who didn’t know her personally still celebrate her fashion legacy that is anchored by the Palm Beach elite.

The story goes that when the famed year-round Palm Beach resident was working at her family’s juice stand on Worth Avenue, to disguise stains on her own clothing, she would have sleeveless dresses made from colorfully-printed cotton. Then, she started selling her designs alongside refreshments. Her dresses immediately sold out, says her daughter, Minnie Pulitzer McCluskey. Soon, she was selling more dresses than juice.

But the first real splash was when Pulitzer’s friend, Jacqueline Kennedy, was photographed on a LIFE magazine cover in 1962 wearing a Lilly Pulitzer dress. “Then, everyone couldn’t get enough of them,” says Pulitzer McCluskey, a real estate agent at Brown Harris Stevens. After, the dresses were simply and unanimously known as Lillys.

The look quickly became a seaside uniform in Florida. It was a dressing style that was fun and vibrant and gave birth to a fashion genre that would be universally touted as “American Resort Wear.” Fast forward from the ’60s to now, and Lilly is still an indisputable everyday brand in Fort Lauderdale and Boca Raton. “The fashion was born under the sun, it served a specific purpose, and it came from a real person with an incredible spirit,” says Eleni McCready, senior manager of social media marketing and public relations for the fashion house. 

The Florida heiress, socialite and fashion designer built her brand to contrast the social norm of the time with her brightly colored shifts that used high slits on the sides. “Lilly loved easy dressing,” McCready says. “The shift was designed to be thrown on and look effortlessly fabulous without the fuss.”

She was the right woman in the right place at the right time. “The stars were aligned over mom, and her bright patterns and classic designs seemed to be exactly what people were looking for,” Pulitzer McCluskey says. 

“Mom’s style and fashion were an extension,” she adds. “The line brought her personality into her clothing. You put on the dresses, and they made you feel happy, and you wanted to have fun.” 

While Lilly Pulitzer is a national brand, it tends to resonate best with Floridians, where year-round palm trees and sunny beaches are the perfect backdrop for playful patterns and bright colors. 

“It’s acceptable to wear a giant palm tree print in the most chic restaurants,” McCready adds. “It’s allowed people to not take things too seriously and smile at the monkey on their shorts. It’s a small way of ‘breaking the rules’ while looking incredible.” 

Amy Mauser, chief development officer for American Red Cross, South Florida Region, echoes the sentiment. “Lilly Pulitzer is classic and her prints have stayed consistent over the years while evolving to meet modern tastes and styles,” she says. 

Pulitzer’s entrée into the world of fashion began as a “happy print-filled accident” when the 20-something heiress opened her first boutique in the Vias off Worth Avenue. “At the time, fashion and resort wear as we know it was just forming. Lilly took the beginnings of resort wear, the classic sailor styles and colors, and turned it upside down,” McCready says. Today, the brand is synonymous with philanthropy. 

The style embellishes topical events such as the Beach Bash, an annual American Red Cross gala in Palm Beach where nearly 900 attendees come donned in full-out Lilly, both vintage and new. With committee involvement from Lilly Pulitzer’s own children and grandchildren, the Beach Bash partnership was a natural, and the Lilly Pulitzer involvement came to set the tone for each year’s new theme, according to Mauser. “Over the last few years the partnership grew and the fashion house has served as the presenting sponsor to bring the ‘Lilly or Louder’ attire to a whole new level,” she says.

Palm Beach socialite and self-proclaimed Lilly enthusiast Richard Gaff, who is a committee member for the American Red Cross Beach Bash, attended December’s Beach Bash dressed in a red vintage bathrobe covered in pink, blue and white flowers.

“Lilly Pulitzer’s style has become so meaningful and iconic because it is more than just a style, it is a representation of a lifestyle,” Gaff says.

Lilly Pulitzer (above) first began making dresses from colorfully printed cotton to disguise juice stains on her clothing while she worked at the family juice stand on Worth Avenue.

“I didn't set out to be unusual or different. I just wanted to do things my way.” - Lilly Pulitzer​

The December event raises funds for the American Red Cross, which provides disaster relief, supports military families and provides health and safety services throughout the local community. 

“It’s exciting to see how Lilly Pulitzer’s legacy can have such a big impact,” Gaff says. 

With its meaningful charitable purpose, the American Red Cross Beach Bash has become the go-to Lilly event. “The brand now represents a carefree, vacation-mindset and lifestyle,” Mauser says.

Plus, men have fun finding vintage Lilly jackets and pants to wear, while the women put on their newest Lilly prints each year. “Even our auction items reflect a Lilly-inspired theme,” she adds. “Their partnership has come to define the evening, and the event has become one of our signature fundraisers—with national attention drawing guests to town from D.C., Manhattan, Charleston and all over.”

The vibrant and fun lifestyle that Pulitzer was so known for permeates the east coast of Florida thanks to fashion, naturally. 

“You can spot a Lilly from across the room,” McCready says. “You wink at someone in a Lilly because you know they will laugh at the same jokes. It’s a bonding element.”

But the bond is deeper and more personal than style.

Although the Pulitzer family no longer owns the label—it was revived by Sugartown Worldwide in the 1990s, sold to Oxford Industries in 2010 and is now based in King of Prussia, Pennsylvania—the family is still closely associated with the brand. 

The Pulitzer legacy is “Family, family, family,” Pulitzer McCluskey says. “Mom’s home was always filled with love, laughter, music, food and family. She shared her heart and home with everyone. She taught all of us the meaning and power of love, graciousness and an open heart. Just thinking about her puts me in a better place.” 

Lilly McKim Leas, Pulitzer’s granddaughter, agrees. “The bold patterns and colorful designs embodied a carefree lifestyle and positive attitude that was contagious,” says Leas, president and owner of Tradewinds Media Partners, a public relations firm in Palm Beach. “It’s fashion that makes you feel something.”

And yet, for Leas, her grandmother’s legacy surpasses what to wear.

“She had the biggest heart in the world, and anyone who had the opportunity to meet her could attest to it,” Leas says. “There was an open-door policy at her house and everyone was treated like family. In Palm Beach, it’s not uncommon for someone to stop me and share a story that I haven’t heard before about Granny and how special she was to them. People felt a special connection to her. We all did. She was amazing.”