Lilly Pulitzer’s Key West Homecoming: A Runway Show and Revival of Iconic Prints

It’s a scene that feels both cinematic and familiar. A seaplane appears as a shimmer of white above Key West’s haute horizon before dropping into the ocean with the grace of a vintage postcard brought to life. The grand entrance echoes the iconic black-and-white photo of Lilly Pulitzer stepping off a seaplane in the 1960s, carefree, sun-kissed and joyfully unbothered by the splash of island living. This past November, history repeated itself. A model, dressed in one of the brand’s revived archival prints, strutted down the Casa Marina waterwalk as aviation partner Tropic Ocean Airways’ seaplane gleamed behind her, a nostalgic reminder of the arrivals that first brought Lilly Pulitzer to Key West. It’s playful, nostalgic and unmistakably Key West. Because here, the destination is the true protagonist.

Key West has long been a muse—a tropical palette of sun, surf and stories lived barefoot—and it welcomed Lilly Pulitzer back for a homecoming as vibrant and storied as the island itself. The brand unveiled its spring/summer 2026 collection with a “brand homecoming” runway show at Casa Marina Key West, Curio Collection by Hilton, a multiday celebration that honored over six decades of color and creativity while returning archival prints to the island that first inspired them for the next generation. Visit Florida Keys helped anchor the weekend in a true sense of place, showcasing the island’s history, culture and natural beauty for guests experiencing Key West through Pulitzer’s iconic lens.

Casa Marina Key West opened on New Year’s Eve in 1920 and was recently restored, providing the perfect backdrop for the runway event. Its wide lawn and swaying palms framed the oceanfront stage, opening onto the island’s largest private beach, a stretch originally envisioned by Henry Flagler and reimagined by the Lilly Pulitzer creative team. The weekend also marked the debut of the resort’s redesigned “Stay Like Lilly” suites, two oceanfront rooms that immerse guests in the designer’s joyful world. Each suite features hand-painted art, fabrics adorned with archival prints from Lilly Pulitzer’s collection and framed original artwork, creating a narrative that celebrates the brand’s rich design heritage. Debuting alongside the Vintage Vault, which reintroduces the brand’s revived archival designs from 1962 to 1985, Casa Marina became the first Hilton property to bring these historic prints to life through layered patterns, hand-painted art and spatial storytelling. “While designing the spaces, I used layered patterns of varying scale to tell the story of a bygone era that feels as relevant and modern as ever,” says interior designer Amanda Reynal, founder of Amanda Reynal Interiors. “We used the prints in different ways to capture the feeling of spontaneity that defines Lilly’s world. Here, fantasy feels as effortless as a sea breeze, as we conjure the magic of old Key West.” The collaboration, exclusive to Casa Marina, cemented the resort as a centerpiece of the island’s new era of style and heritage.

The celebration began the night before with an intimate dinner at The Ernest Hemingway Home & Museum. Hosted by Mariel Hemingway, Lilly Leas Ferreira and the Lilly Pulitzer brand, the evening brought together storytellers, tastemakers and brand ambassadors to reflect on the art, legacy and exuberant creativity that shaped both the Hemingway and Pulitzer worlds. The historic estate, with its lush grounds and roaming six-toed cats, served as a cultural anchor, reminding guests that Key West has long been a refuge for artists who find inspiration in the island’s eccentric charm.

The following morning, the island became a living runway. Historic Tours of America guided guests through Key West’s sun-soaked streets aboard the Conch Tour Train and Old Town Trolley, rolling past pastel homes, tropical gardens and landmarks that helped shape the island’s legacy. On the water, Danger Charters hosted a VIP sailing excursion, where influencers lounged on deck in bright resort silhouettes as sea spray drifted across archival prints like Chicken Check and Rosie’s Petals.

As the sun dipped toward the horizon, the runway show unfolded on Casa Marina’s oceanfront lawn. Archival prints, some not seen since the 1960s, fluttered in the breeze as models walked toward the water’s edge, a palette of pinks, greens and blues echoing the landscape around them. The crowd included A-listers like Stephanie Hill (@thestylebungalow), Logan Leone (@logantay), Hannah Leigh (@hannnah.leigh.c), Paris Bamberg (@parisbamberg) and photographer Nick Mele (@nickmelephotography), among others. It was a true homecoming, celebrating the artistry and optimism that have defined Lilly Pulitzer for generations and signaling a vibrant new chapter for the brand. The evening eased into a sunset afterparty on Casa Marina’s sand, where pink and orange skies mirrored the playful prints worn by guests as music drifted over the water and cocktails were raised under pastel umbrellas.

With a renewed commitment to culture, storytelling and hospitality, Key West is entering a new era that honors its storied past while embracing the possibilities ahead. “At Casa Marina, our priority is creating meaningful, memorable stays for every guest who walks through our doors,” says Evelyn Summer, hotel manager of Casa Marina Key West. “Partnering with a beloved brand like Lilly Pulitzer allows us to offer an experience that feels both iconic and uniquely tied to the spirit of Key West.”

It’s a reminder that sunshine isn’t just something you find; in Key West, it’s something you create.“Stay Like Lilly” suites available through Nov. 15, 2026, Casa Marina Key West, Curio Collection by Hilton, 1500 Reynolds St., Key West, hilton.com; lillypulitzer.com