LOUISVILLE, Ky. — Dannielynn Birkhead stepped onto the red carpet of the Barnstable-Brown Gala on May 2, 2025, in a black halter gown that carried the weight of memory. The 18-year-old daughter of the late Anna Nicole Smith chose a dress her mother wore to the same Kentucky Derby eve event 21 years earlier, in 2004. The floor-length number, with its plunging neckline and crystal-studded straps, shimmered under the lights, but for Dannielynn, it was more than fashion. “This is the closest to a hug I can get from her,” she told a reporter, her voice catching as she honored the mother she lost at five months old.
The gala, a glitzy staple of Louisville’s Derby weekend, has long been a touchstone for the Birkhead family. Larry Birkhead, Dannielynn’s father, stood beside her, snapping photos and sharing the moment on Instagram. He called it a “full circle” night, noting the gown’s history—Anna Nicole, then a tabloid supernova, had turned heads in it at the same mansion two decades ago. The dress, preserved for years, stirred raw emotion for Larry. He recalled Dannielynn, as a child, touching the fabric, drawn to it instinctively. Now, seeing his daughter wear it, he admitted the sight hit hard.
Dannielynn, blonde hair pinned up like her mother’s in 2004, moved through the crowd with quiet poise. The gown’s daringly low back and rhinestone accents echoed Anna Nicole’s bold style, a reminder of the model’s larger-than-life presence. Anna Nicole, born Vickie Lynn Hogan, died on February 8, 2007, at 39, from an accidental drug overdose, leaving behind a legacy as complex as her public life. Dannielynn, raised by Larry in Kentucky, has largely stayed out of the spotlight, making these annual Derby appearances a rare glimpse into her world.
The night wasn’t just about the dress. Dannielynn, who’d worn a Janet Jackson gown to another event the previous evening, debuted a fresh haircut for Derby Day, signaling her knack for reinventing herself while nodding to the past. The Barnstable-Brown Gala, held at the Barnstable-Brown Mansion, draws celebrities and locals alike, raising funds for diabetes research. For the Birkheads, it’s a tradition tied to Anna Nicole, who first attended in 2003, dazzling in a light blue gown.
Larry, a photographer who met Anna Nicole at this very event, has made the gala a yearly ritual for him and Dannielynn, a way to keep her mother’s memory alive. He shared that Dannielynn picked the dress herself, calling it “super cool” for its connection to her mom. The moment resonated beyond the family—attendees noted Dannielynn’s striking resemblance to Anna Nicole, from her features to her poised stride.
The gala unfolded against the backdrop of the 2025 Kentucky Derby, set for May 3 at Churchill Downs. Dannielynn and Larry planned to attend the races, continuing a tradition that’s become a public marker of their bond. For one night, though, it was the dress that spoke loudest, a tangible link to a woman whose life burned bright and brief.
Dannielynn Birkhead is 18. Anna Nicole Smith died at 39. The Barnstable-Brown Gala occurred on May 2, 2025. The Kentucky Derby was scheduled for May 3, 2025.