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Dannielynn Birkhead debuts edgy look at Kentucky Derby gala

3:26
Anna Nicole Smith’s daughter learns more about her mom’s past
Stephen J. Cohen/Getty Images
ByBethany Braun-Silva
May 02, 2026, 3:51 PM

Dannielynn Birkhead is stepping out in style once again for Kentucky Derby weekend, continuing a long-standing family tradition with her father, Larry Birkhead.

The 19-year-old daughter of Birkhead and the late Anna Nicole Smith attended the annual Barnstable Brown Derby Eve Gala on May 1. The outing has become an annual event for the father-daughter duo, who often share glimpses of the night on social media.

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According to a post shared on their joint Instagram account, Dannielynn embraced a bold look for the evening. She wore a strapless gothic-inspired dress from Punk Rave, featuring intricate embroidery and a sheer, draped skirt.

Dannielynn also debuted a dramatic new hairstyle, a fresh short cut styled in icy platinum tones with dark tips.

Larry Birkhead also joined in on the theme, sporting a statement jacket from Philipp Plein, as noted in the caption. The post highlighted the coordinated styling approach, with Dannielynn “rocking a fresh cut and ‘goth-rock’ style” while encouraging her father to match the vibe for the night.

Dannielynn Birkhead attends the 152nd Kentucky Derby - Barnstable Brown Gala at Barnstable-Brown Mansion, on May 1, 2026, in Louisville, Kentucky.
Stephen J. Cohen/Getty Images

The Instagram caption also credited the glam team behind the look, including hairstylists and makeup artists who helped bring the edgy transformation together.

The Barnstable Brown Gala, held annually ahead of the Kentucky Derby, is known for drawing celebrities and high-profile guests while supporting charitable causes. For Dannielynn and Larry, it has also become a meaningful tradition, one they have attended together for more than 15 years.

Last year, Dannielynn made headlines for a more sentimental fashion moment at the same event. At the 2025 gala, the then-18-year-old honored her late mother by wearing the same gown Smith had worn to the Barnstable Brown Gala in 2004.

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