Watch: Anna Nicole Smith’s Daughter Dannielynn Birkhead Debuts “Goth-Rock” Look at Kentucky Derby 2026
Dannielynn Birkhead was not horsing around with her 2026 Kentucky Derby party look.
The daughter of the late Anna Nicole Smithmade quite the statement at the annual Barnstable-Brown Gala on May 1, wearing a drapey black dress alongside a new ‘do.
Indeed, the 19-year-old’s wispy pixie cut stole the show, featuring silver roots and brown tips.
“Another year another Barnstable-Brown Gala for the @Kentuckyderby weekend,” Dannielynn’s dad Larry Birkhead wrote on Instagram May 1 alongside a photo of the father-daughter duo. “Dannielynn is rocking a fresh cut and “goth-rock” style with her @punkraveclothing dress.”
And Larry took a few style pointers from his little girl ahead of the soirée.
“She insisted I get in on the theme with my Phillipp Plein jacket,” Larry added. “Looking forward to a great time for a great cause.”
As for what he thinks about the teen’s new haircut?
Noting that his daughter “wanted something edgy and cool” for her tresses, Larry told People he was “bracing himself” at the hair salon as she “chopped it all off and put some wild colors in it.”
“We’ve got this total style change up for her,” Larry added of Dannielynn, who has previously worn bright colors to past events. “And this is kind of, I think her coming into her own, doing her own thing and kind of exuding her own style and her choices that she made.”
Dannielynn is no stranger to the Derby. After all, the model has attended the event every year since 2010 with Larry, who dated Anna Nicole from 2005 to 2006.
Instagram/Larry Birkhead
And each time Derby Weekend rolls around, Dannielynn and Larry make sure to rock memorable—and coordinating—looks.
Last year, the two attended the Barnstable Brown Gala in matching black attire. Dannielynn wore the same backless gown her late mom wore to the event 21 years prior as well as a loose updo like her mother. Meanwhile, her dad matched in a classic black suit and tie.
The following day, for the race at Churchill Downs, Dannielynn wore a mint-colored, off-the-shoulder gown with layered tulle. She accessorized her look with a yellow flower headband and a matching necklace. And of course, her father coordinated in a beige suit with pops of mint and yellow in his pocket square, tie and lapel pin.
But the annual outings weren’t always the plan for the father-daughter duo. In fact, Larry previously admitted that the joint appearances were actually a last-minute decision due to circumstances out of his control 16 years ago.
Stephen J. Cohen/Getty Images
“I think the one year the babysitter canceled,” he told E! News in 2024. “And then it became I brought her when she was able to kind of walk and do her own thing down the carpet, and then it became a tradition.”
But since then, the pair couldn’t be happier getting to attend the event together each year.
“We had such a great time,” Larry wrote in an Instagram post last year after the weekend festivities. “An unbelievable full circle moment seeing Dannielynn shine at The Barnstable-Brown Gala wearing her Mom’s iconic dress from the same event. Hearing Dannielynn share her thoughts when she was asked about what that meant was an emotional yet proud Dad moment.”
The tradition is also incredibly meaningful, now that Dannielynn is officially an adult.
“It’s a moment you cherish, you look up and time’s flown,” Larry said in a 2025 interview with Access Hollywood. “I got her to the finish line hopefully, and now she has a good foundation to go on and do great things.”
For a look back at all of Dannielynn’s Kentucky Derby looks over the years, keep reading…
Mike Coppola/Getty Images
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Mike Coppola/Getty Images
Neilson Barnard/Getty Images
Gustavo Caballero/Getty Images for Churchill Down
Michael Loccisano/Getty Images for Churchill Downs
Dia Dipasupil/Getty Images for Chruchill Downs
AFF-USA/Shutterstock
Stephen Lovekin/Shutterstock
Instagram / Larry Birkhead
Instagram / Larry Birkhead
Instagram / Larry Birkhead
Instagram / Larry Birkhead
Michael Loccisano/Getty Images
Daniel Boczarski/Getty Images for Churchill Downs
Stephen J. Cohen/Getty Images
Instagram / Larry Birkhead
Instagram / Larry Birkhead
Jeff Schear/Getty Images for Churchill Downs
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