Dannielynn Birkhead Rocks Goth Look at Kentucky Derby 2026 Party

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Dannielynn Birkhead was not horsing around with her 2026 Kentucky Derby party look.

Dannielynn Birkhoff, the daughter of the late Anna Nicole Smith, turned heads at the Barnstable-Brown Gala on May 1st. She wore a flowing black dress and debuted a fresh new hairstyle.

Indeed, the 19-year-old’s wispy pixie cut stole the show, featuring silver roots and brown tips.

Larry Birkhead shared a photo on Instagram May 1 of himself with his daughter, Dannielynn, at the annual Barnstable-Brown Gala during Kentucky Derby weekend. He noted Dannielynn debuted a new haircut and a ‘goth-rock’ look with a dress from @punkraveclothing.

And Larry took a few style pointers from his little girl ahead of the soirée.

Larry said she really wanted me to participate in the event’s theme and wear my Philipp Plein jacket. He’s excited about having a good time and supporting a worthy cause.

As for what he thinks about the teen’s new haircut?

Larry explained to People magazine that his daughter was looking for a bold, modern hairstyle. He admitted he was nervous while at the salon as she dramatically cut off her hair and dyed it in vibrant colors.

Larry explained that Dannielynn has undergone a noticeable style transformation. Unlike her previous preference for bright colors, this new look represents her developing individuality and confidence in making her own fashion choices.

Dannielynn has been a regular at the Kentucky Derby since 2010. She attends each year with Larry, who was in a relationship with her mother, Anna Nicole Smith, from 2005 to 2006.

Every year for the Kentucky Derby, Dannielynn and Larry always dress in outfits that are both eye-catching and perfectly matched.

As a lifestyle expert, I always appreciate seeing heartfelt tributes, and last year’s Barnstable Brown Gala was a beautiful example. Dannielynn and her dad were a striking pair in black, but what really touched me was Dannielynn choosing to honor her late mother by wearing the very same gown she wore to the gala 21 years ago! She even styled her hair in a similar, loose updo. It was a sweet and touching way to keep her mother’s memory alive, and her dad looked incredibly proud beside her in a classic black suit.

For the race at Churchill Downs the next day, Dannielynn wore a beautiful mint green dress with layers of tulle, and finished the look with a yellow flower headband and necklace. Her father complemented her outfit in a beige suit, adding touches of mint and yellow with his pocket square, tie, and lapel pin.

These yearly outings weren’t originally planned for Larry and his daughter. He’s shared that their first joint appearance happened unexpectedly 16 years ago, due to circumstances he couldn’t avoid.

He recalled a time when their babysitter had to cancel, which led to him starting a tradition of bringing his daughter along. He explained to TopMob News in 2024, “She was at the age where she could walk around and entertain herself, and it just sort of stuck.”

But since then, the pair couldn’t be happier getting to attend the event together each year.

Larry shared on Instagram last year how much he enjoyed the weekend, especially watching his daughter, Dannielynn, at The Barnstable-Brown Gala. He was incredibly moved to see her wearing her mother’s famous dress from the same event, and even more touched when she talked about what it meant to her. He described it as a very emotional, but proud, moment as a father.

The tradition is also incredibly meaningful, now that Dannielynn is officially an adult.

In a 2025 interview with Access Hollywood, Larry described it as a special moment, saying, ‘You realize how quickly time has passed.’ He added that he hoped he’d helped her succeed and that she now has a strong base to build on and achieve great things.

For a look back at all of Dannielynn’s Kentucky Derby looks over the years, keep reading…

She’s her mother’s daughter, all right!

Who needs a fascinator when you’re this fabulous?

Flower power! Anna Nicole’s mini-me’s fascinator is in full bloom.

Chim chim cheree! The daddy-daughter duo take inspiration from Mary Poppins.

Larry leads the way as Dannielynn smiles for the cameras.

Think pink! Dannielynn and Larry pick coordinating colors for their festive frocks.

At just 10 years old, Dannielynn is already a red carpet veteran!

Everything’s coming up roses for the twosome!

Dannielynn and her dad are feeling blue, in a good way!

The tween is all smiles in a yellow floral dress as she poses with her dad.

Dannielynn and Larry went to the 2019 Kentucky Derby. Larry shared on Twitter that Dannielynn looked lovely in a pink dress by Junona and a hat originally worn by her mother at the 2004 Kentucky Derby. He used the hashtag #KentuckyDerby2019.

All smiles!

Masked up!

Dannielynn and her father, Larry, were spotted at the Kentucky Derby celebrations, wearing outfits that matched each other, a day before the main event.

Larry and his daughter, Dannielynn, attended the 2022 Barnstable-Brown Gala, a party held before the Kentucky Derby. Dannielynn wore a dress originally worn by Janet Jackson at the same gala in 2003. Larry explained that he bought the outfit at a Julien’s Auction, and the purchase supported a charitable cause.

I was so happy to see Dannielynn Birkhead, Anna Nicole Smith’s daughter, looking so grown up and vibrant at the 2022 Kentucky Derby! She’s fifteen here, posing with her dad, Larry Birkhead, and they both looked fantastic. It was a really sweet moment.

Sixteen-year-old Anna enjoyed a stylish outing with her father, Larry Birkhead, after honoring her late mother with her outfit at the Barnstable Brown Kentucky Derby Eve Gala in May 2023.

Okay, let me tell you about this incredible look! I spotted a gorgeous 17-year-old at the Barnstable Brown Kentucky Derby Eve Gala in May. She was wearing a stunning Gianfranco Ferre dress – and get this – it used to belong to Janet Jackson! She actually snagged it at Julien’s Auctions, which is just amazing. It’s such a cool piece of fashion history, and she wore it beautifully.

The 17-year-old was seen with her father, Larry Birkhead, heading to the 2024 Kentucky Derby, sporting a fresh lob haircut.

During the 2025 Kentucky Derby weekend, 18-year-old Dannielynn Birkhead attended the Barnstable Brown gala with her father, Larry Birkhead, wearing the same dress her mother famously wore to the event in 2004.

The two coordinated in aqua at the main event.

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2026-05-02 16:17