Anna Nicole Smith’s Kentucky Derby Style Lives On Through Her Daughter

For Anna Nicole Smith, the Kentucky Derby was more than just a horse race; it was both a runway and a promotional platform. The model left her mark at the event in the early noughties, joining a bevy of stars who transformed the event’s relationship with Hollywood and fashion.

Established in 1875, the Kentucky Derby became a celebrity sighting hotspot in the early 2000s, with Smith, Janet Jackson, Pamela Anderson, Kim Cattrall and others popular Y2K names embracing the event’s sartorial fashion style. Smith attended the horse race two years in a row and featured the event in one of the episodes of her reality TV series, “The Anna Nicole Show.”

Known for her eye-catching fashion choices and vibrant style, Smith debuted at the event in 2003, attending the pre-Kentucky Derby Barnstable-Brown party in a light blue strapless gown with sparkling embellishments. The floor-length dress had a fitted bodice and was paired with a matching light scarf or wrap.

For the horse race that year, she wore a navy blue outfit with a distinctive white lace or ruffled collar and cuffs. She’s also sported a wide-brimmed hat in the same dark color as her outfit.

In 2004, Smith returned to the Barnstable Brown party, this time wearing a black backless dress with multiple rhinestone straps across the open back. The dress featured a dramatic plunging neckline accented with crystal embellishments down the front.

The next day, she changed into a springtime pink dress featuring a sequined V-neck silhouette. The look was complete with a matching pink hat, jeweled Christian Dior heels and a peony blossom purse.

Both looks from Smith’s 2004 appearance at the Kentucky Derby were later loaned to the Kentucky Derby Museum in 2010 by her former partner, Larry Birkhead, who she met at the event. “Larry was so generous to think of us and we hope that it starts a trend of displays that the public is excited to see,” Lynn Ashton, executive director of the museum, said via statement at the time.

Smith died in 2007, but her relationship with the Kentucky Derby continued through her daughter, Dannielynn Birkhead, whom she shared with Larry.

Dannielynn has honored her mother by wearing pieces inspired by or directly connected to Anna Nicole Smith’s style at Derby events through the years. For instance, in 2019, while attending the event with her dad, Dannielynn wore Smith’s 2004 pink hat. In 2024, Dannielynn wore a taffeta floral Badgley Mischka gown featuring statement sleeves and a matching belt, nodding to her mom’s vibrant style.

Dannielynn and Larry Birkhead have attended the Kentucky Derby every year since 2009. The 2025 Kentucky Derby will be held at Churchill Downs in Louisville on Saturday.