Anna Nicole Smith's Daughter Dannielynn Birkhead Has Had Quite The Style Transformation

Side-by-side pics of Dannielynn Birkhead at the Kentucky Derby show her personal style evolution, and it's only getting better as the years go on. Birkhead, who is 19-years-old at the time of writing, has been in the spotlight since childhood as the daughter of the late Anna Nicole Smith and Larry Birkhead. Between attending galas starting at the age of three and modeling different pieces of clothing for larger brands, Birkhead hasn't always had the space to express her personal sense of fashion in the public eye. Under the guardianship of her father, she's navigated life in the public eye under a narrative that presents her as whimsical and colorful.

Since Anna Nicole Smith's untimely passing in 2007, many have compared Dannielynn to her mother because of how similar they look. While she's grateful that people are still supportive of her mother after all these years, she's made it clear that she's her own person and planning to continue to make moves that make her feel empowered– including her fashion choices. 

Dannielynn and Larry Birkhead have been attending the Kentucky Derby every year since she was a child. Each year, the styles she's presented have been colorful and incorporate some type of floral print or accent. Specifically in 2017, the 10-year-old could be seen wearing a light pink dress with 3D floral appliques. She styled this with a matching pink and purple fascinator and floral sandals. She tied the look together with a pink multilayered bracelet that matched seamlessly with the outfit. 

Though Dannielynn Birkhead's appreciation for florals continued through the years, by 2023, she started taking a more elevated approach on the style, trading in youthful pinks for more artful hues. For the Kentucky Derby that year, the then 16-year-old sported a light blue, floor-length gown by Leo Lin,  that featured a painted sunflower design, which was such an attention grabber. To make the moment even more memorable, she styled the look with a crystal jewelry that belonged to her mother.

By 2024, Dannielynn Birkhead was starting shift into a gothic style that was a far departure from her previously frilly, floral looks. For her 18th birthday, she sported a black sheer two-piece skirt set with spider web detailing from Hot Topic while attending the Beetlejuice Afterlife Experience. The top was a trendy, cold-shoulder design featuring mesh bell sleeves. Birkhead also clearly was in a new era for accessories, as other photographs for the day show her sporting large, pink circle glasses and old-school chunky cross necklaces.

Side-by-side pics of Anna Nicole Smith and daughter Dannielynn Birkhead will have you seeing double, and the resemblance is further underscored when the latter channels her mother's style. This was especially seen during the 2025 Barnstable Brown Gala, where Birkhead wore the same dress Smith did in 2004 for the same event. Along with being a fitting tribute to her late mother, the outfit marked a notable shift in Birkhead's style; gone were the bright colors of her youth, as she embraced a more glamorous, mature look. She rocked the piece with a thick diamond bracelet and silver ring that strongly complemented the silver detailing in the back of the dress.

Figuring out your own style while growing up in the spotlight is never easy. As of 2026, Dannielynn Birkhead is actively working on reclaiming her voice and unapologetically showing the world who she truly is through her fashion.  In an interview with Access Hollywood, she revealed her desire to look like a vampire daily and hone in on a grunge look that she wears more at home. As seen in the Barnstable Brown Gala from that year, Birkhead was seen channeling this aesthetic with an an all-black high-low dress and a black and silver bracelet. Her black tipped blond hair completed the look.