Anna Nicole Smith’s Daughter Honors Her at Kentucky Derby Gala

Anna Nicole Smith’s daughter, Dannielynn Birkhead, paid homage to the late model by taking one of her vintage gowns out on the town.

“Kicking of @kentuckyderby weekend with Dannielynn,” the 18-year-old’s father, Larry Birkhead, wrote in a Friday, May 2 Instagram post featuring family pics. “First up, The Barnstable-Brown Gala. Dannielynn is wearing Anna Nicole’s dress that she wore 21 years ago to this same event. Life full circle. She said she chose the dress because it was her Mom’s and ‘super cool.’”

Dannielynn was all smiles while sporting the black halter gown, which has a plunging neckline, open back and sparkly detailing. Her long, blond hair was piled atop her head, recalling her mom’s hairstyles in the 1990s and 2000s.

“Next up the Kentucky Derby races,” Larry, 52, captioned his post. “We are glad to spend time with my niece Chloe (pictured). I am going to try not [to] embarrass them with my dance moves.”

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Larry and Dannielynn have previously attended Derby festivities in Louisville, Kentucky. A year ago, they posed for photos before making their way to the racetrack. Dannielynn wore a bright red Badgley Mischka gown and coordinating Jane-Rose Zupetz fascinator, while her dad sported a light gray suit and a purple tie. 

“We are having a great time,” Larry exclusively told Us Weekly in May 2024. “Dannielynn is enjoying one of [her] first years getting into the fashion of the Derby. She wore a dress that was Janet Jackson’s on Friday and got a major haircut because she wanted ‘another look’ for Derby Day.”

The night before Derby Day, the father-daughter duo hit the Barnstable-Brown Gala at Barnstable-Brown Mansion in Louisville. Dannielynn donned a floor-length, long-sleeved Gianfranco Ferré dress that was bought at auction from a collection that once belonged to Jackson.

The gala holds a sentimental place in the hearts of the Birkhead family.

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“Tonight is the 20th anniversary where I met Dannielynn’s Mom at the same event,” Larry shared via Instagram in 2023. (Smith died of a drug overdose in February 2007 at the age of 39, just five months after Dannielynn was born.)

“Sometimes you feel like a bodyguard, sometimes you feel like a chauffeur,” Larry joked to Us in 2020 about being a single father. “It depends on what the day is. But my job is dad and I think I’ve done a pretty good job. She’s adjusted to it and she’s just a normal kid.”