Anna Nicole Smith’s Daughter ‘Chopped It All Off’ For Derby Look

Dannielynn Birkhead is stepping into the spotlight and doing it entirely on her own terms. The 19-year-old daughter of Anna Nicole Smith made a striking appearance during Kentucky Derby weekend, showing off a dramatic new style at the annual Barnstable Brown Derby Eve party. Accompanied by her father, Larry Birkhead, Dannielynn turned heads with a fresh pixie haircut featuring black tips and a gothic-inspired ensemble that marked a clear departure from her past looks.

According to Larry, the moment was all about his daughter embracing her individuality. “People [are] always looking for her to wear something of her mom. And she’s done that a couple times, but this is kind of Dannielynn showing off her own sense of style, and she said it’s a goth rock theme,” he told PEOPLE.

The look featured a Punk Rave Gothic-inspired strapless corset gown paired with a flowing sheer skirt, a bold evolution from the brighter styles she’s worn to the event in previous years.

Dannielynn Birkhead Debuts Edgy Hair Makeover As Dad Admits He Was ‘A Little Worried’

Dannielynn’s edgy new hairstyle was also a major talking point. “She wanted something edgy and cool,” Larry shared, revealing that a hairstylist who had been a friend of her late mother helped bring the vision to life. “She chopped it all off and put some wild colors in it. I was kind of bracing myself at the hair salon,” he added with a laugh. “I guess she’s at the age to do what she wants to do.”

While the transformation surprised him at first, Larry admitted he ultimately supports his daughter’s decisions. He said he was “a little worried about it” initially, but acknowledged that she’s “obviously old enough” to make her own choices. “This year is a different style for Dannielynn, 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 Birkhead Juggles Finals While Styling Dad For Derby Night ‘Fashion Upgrade’

The look didn’t come together without a little stress. Larry revealed that Dannielynn was juggling school finals while planning her outfit, forcing them to coordinate remotely. “Although it was tough because she was in school taking finals, so I had to help kind of send these pictures back and forth, and then she kind of eliminated one by one, and then I think she got to the end and said, ‘Quit bothering me. I’m in finals,’ ” he said.

The fashion moment didn’t stop with her own outfit. Dannielynn also helped upgrade her dad’s look for the night. “She said I needed to up my fashion game,” Larry joked. “That I had no sense of style. And so she was determined to pick my outfit out.”

He ended up wearing a black blazer adorned with rhinestones and lightning bolt detailing, calling the finished look “very wild” for him.

Dannielynn Birkhead Honors Anna Nicole Smith While Stepping Into Her Own Spotlight

Though this year’s look was all about carving her own identity, Dannielynn has often honored her late mother through fashion. After Anna Nicole Smith’s death in 2007, when Dannielynn was just 5 months old, the Kentucky Derby has become a meaningful tradition for the pair.

Over the years, she’s worn pieces that once belonged to her mother, keeping that connection alive while growing into her own spotlight. Now, with this latest appearance, it’s clear Dannielynn is balancing both, honoring the past while confidently stepping into her own future.

Kentucky Derby 2026 Set To Bring High Stakes Racing And High Fashion

As the spotlight shifts from red carpets to the racetrack, the Kentucky Derby is set to take place on Saturday, May 2, 2026, with post time scheduled for 7:02 p.m. ET. This year’s race is already generating buzz, with contenders like Commandment, So Happy, Renegade, and Further Ado among the early favorites based on morning line odds. But beyond the competition, the Kentucky Derby remains just as much about fashion as it is about racing.

Often dubbed the “Run for the Roses,” the event is known for its over-the-top style moments, from bold, wide-brimmed hats and fascinators to vibrant dresses and tailored suits that rival any red carpet. With standout looks already turning heads during Derby weekend events, the main race is expected to deliver both thrilling finishes on the track and unforgettable fashion moments off it.