21 Years Later: Dannielynn Birkhead Dazzles in Mom Anna Nicole Smith’s Iconic Dress at the Kentucky Derby

All bets are off—Dannielynn Birkhead stole the spotlight at the 2025 Kentucky Derby!

The 18-year-old made a heartfelt choice by wearing a stunning black dress that once belonged to her late mother, Anna Nicole Smith, at the Barnstable-Brown Gala. This gown first graced the event in 2004.

Her father, Larry Birkhead, shared a touching photo on Instagram, saying, “Kicking off @kentuckyderby weekend with Dannielynn. She chose this dress because it was her Mom’s and ‘super cool.’”

As they prepared for the Derby, Larry humorously noted he would try to keep his dance moves in check around his niece, Chloe.

Fans quickly took to social media to express their admiration for Dannielynn. One commenter wrote, “You both look amazing! Dannielynn is such a beautiful young lady.” Another added, “The resemblance is unreal,” proving that she carries on her mother’s legacy.

For Dannielynn, the dress symbolizes a connection to her mother, who passed away in 2007. She shared with reporters that wearing it feels like getting a hug from Anna Nicole.

Larry, who has saved Anna Nicole’s wardrobe over the years, estimated he’s spent more than $200,000 on storage bills for her belongings. He hopes Dannielynn finds joy in these pieces as she grows older and discovers her mother’s world.

Reflecting on the emotional moment, Larry said, “The last time I saw that dress, it was on Anna. Now seeing Dannielynn in it is surreal.” He added that he appreciates her experimenting with fashion, as it allows her to connect with her mother’s spirit.

The father-daughter duo isn’t new to Derby festivities—they’ve attended every year since Dannielynn was just three, turning it into a cherished tradition.

In previous years, Larry expressed pride in how Dannielynn has begun to embrace Derby fashion. “She wore a dress that belonged to Janet Jackson last year,” he recalled. “It’s beautiful watching her style evolve.”

The Barnstable-Brown Gala is especially meaningful for Larry as it’s where he first met Anna Nicole Smith. Each year, they make it a priority to attend, keeping the memories alive.

Anna Nicole’s career began in 1992 with Playboy and continued to blossom into major brand collaborations. Sadly, she passed away at 39, just five months after giving birth to Dannielynn. The tragedy deepened when her son, Daniel, died of an overdose a year earlier.

Daniel had the chance to meet Dannielynn before his untimely death, leaving behind a heart-wrenching legacy intertwined with that of his mother and sister.

As the Kentucky Derby continues to evolve, the Birkhead legacy remains strong, reminding us of the power of love, remembrance, and connection through the passing of generations.

For more heartfelt insights on this touching story, you can visit People.

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Entertainment,Celebrities,anna nicole smith,celebrity children,death,family,kentucky derby,larry birkhead