“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.

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.

“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…