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All bets are off — Dannielynn Birkhead wins best look at the 2025 Kentucky Derby.
The 18-year-old donned a very special dress for the festivities, wearing the same gown her mom, the late Anna Nicole Smith, wore in 2004.
“Kicking of @kentuckyderby weekend with Dannielynn,” her dad, Larry Birkhead, captioned his Friday Instagram post. “First up, The Barnstable-Brown Gala. Dannielynn is wearing Anna Nicole’s dress that she wore 21 years ago to this same event. Life full circle. She said she chose the dress because it was her Mom’s and ‘super cool.’”
“Next up the Kentucky Derby races,” Larry, 52, continued. “We are glad to spend time with my niece Chloe (pictured). I am going to try not an embarrass them with my dance moves.”
In the snap, Dannielynn flashed a huge smile as she sported the dazzling black halter dress. The gown featured a plunging neckline with sparkles down the center and around the back, and an open slit.
Dannielynn’s hair was also a nod to Anna Nicole, who died in 2007 from an accidental drug overdose. She wore her blonde locks in a soft updo like her mom did in the early aughts.
Fans flocked to the comments section to share their love for the late model’s mini-me, with one person writing, “You two look so incredibly amazing! Very sharp Larry and DannieLynn has grown to be a beautiful young lady,”
A second gushed, “Stoppp the resemblance is unreal.”
Rounding out the sweet remarks, a third social media fan commented: “You both look amazing!!! At first glance, I saw Anna and thought it was a very old pic. Wow, does Dannielynn look like her Mother. To see her all glammed up like that, she looks like a beautiful young lady coming into her own. Lots of love from me.”
While on the carpet, Dannielynn remarked to a reporter that wearing the dress “is the closest to a hug I can get from her.”
Larry spoke to People about the heartfelt moment, sharing he’s had the dress “for years,” but it was “emotional” to see Dannielynn wearing it.
“It was emotional because the last time I saw that dress was on Anna,” admitted Larry, who recalled that when Dannielynn “was a little girl, she walked over and she put her hand on the dress.”
“And now that she’s actually old enough to wear it, it just seems surreal that we’re at this moment.”
Getting candid on picking the black number in particular, Larry explained “I think she’s doing a fashion experiment for herself. Also, I think it’s really meaningful for her to wear. I’m just glad she’s going through and starting to wear some of [Smith’s clothes] because she could literally pick out an outfit a day for the rest of her life and never wear the same thing twice with everything.”
The dad-of-one has in fact saved all of Anna Nicole’s clothing, spending “over $200,000 in storage bills” to save all of the late star’s belongings to pass down to Dannielynn.
“[I] just hope that she would appreciate some of these things someday,” noted Larry. “She’s just now starting to get into the curiosity of some of the fashion and things in her mom’s world.”
“When somebody passes away, you think, ‘Oh, I’m not getting rid of anything. And then you go through the emotions of, okay, do I really want this? Do I really need this? … and you think, ‘Well, if there’s just one thing in there that she can connect with, that gives her a sense of who her mom was. So it was really special that she picked out the dress to wear.”
Larry and Dannielynn are no stranger to the Derby in Louisville, Kentucky, as the father-daughter duo have gone together every year since she was 3 years old. As for why they started so young, Larry confessed it “was really born out of the babysitter cancelling on me the first year I brought her!”
“And then everybody was like, ‘Oh, how cute. And then I thought, ‘Well, she wasn’t that much trouble last year. So it became a tradition,” he expressed. “Then people started looking for us and then the outfits had to be bigger.”
Last year, the photographer gushed over how the teen has been able to embrace the fashion of the south on her own for the first time.
“We are having a great time,” Larry told Us Weekly in May 2024. “Dannielynn is enjoying one of [her] first years getting into the fashion of the Derby. She wore a dress that was Janet Jackson’s on Friday and got a major haircut because she wanted ‘another look’ for Derby Day.”
Before Derby Day, Larry and Dannielynn always make it a point to attend the Barnstable-Brown Gala at Barnstable-Brown Mansion in Louisville.
The gala is a meaningful spot for the pair, as Larry revealed on Instagram in 2023: “Tonight is the 20th anniversary where I met Dannielynn’s Mom at the same event.”
Anna Nicole had iconic style all throughout her career, which she started in Playboy magazine in 1992. The starlet went on to model for H&M, Guess and other major retail brands.
The actress’s death came at age 39, just five months after the birth of Dannielynn. Prior to her passing, Anna Nicole’s son, Daniel, who she had at 17 with her former husband Billy, died a year earlier in 2006 at 20 years old. He also died of an accidental drug overdose.
During a hearing after her death, the television personality’s then-boyfriend Howard K. Stern said, “Anna and Daniel were inseparable. Daniel was without question the most important person in Anna’s life.”
It was reported that at Daniel’s funeral, Anna Nicole tried to climb into his coffin.
“He comes to me in my sleep …,” she told Entertainment Tonight ten days before her death. “It’s like he’s calling me to come to him.”
Daniel did get to meet Dannielynn before his death, having gone to the hospital to see his mom and sister the night before he died.
“When Daniel arrived in the hospital room he went straight to his baby sister. He embraced his mother and sister and told them both that he loved them,” her lawyer Michael Scott said in a statement in 2006. “Daniel was very helpful to his mother and baby sister. On several occasions throughout the night, Daniel assisted his mother to the bathroom, as she was still in a lot of pain from her C-section.”
After the death of Daniel, Howard claimed he was the father of Dannielynn – to which Larry filed a paternity suit and he was found to be the father.
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