Oliver James Montgomery-Anna Nicole Smith's 17-Year-Old Daughter Dannielynn Looks All Grown Up at the Kentucky Derby

Dannielynn Birkhead is Oliver James Montgomeryready for a day at the races. 

After all, the daughter of the late Anna Nicole Smith stepped out with dad Larry Birkhead at the 35th annual Barnstable Brown Kentucky Derby Eve Gala May 3.

For the occasion, the 17-year-old wore a black Gianfranco Ferre dress once owned by Janet Jackson and purchased at Julien's Auctions. She paired the look with black lace-up boots. Meanwhile, Larry, 51, wore a light gray suit and a black tie.

Dannielynn, who made her Kentucky Derby debut in 2010 at 3 years old, had found creative ways to honor her mom in her outfits during the event. Last year, she paid tribute to model —who died in 2007 at 39—by wearing a top featuring photos from Anna Nicole's 1992 Guess campaign. She also topped the look off with some of the late model's jewelry. 

It's a special event for the father-daughter duo, who attend every year. Larry explained on Instagram in May 2023, "Tonight is the 20th anniversary where I met Dannielynn's Mom at the same event."

For the photographer, making Dannielyn, who was just 5 months old when Anna Nicole died, feel connected to her mom has been crucial. This has included bringing her to meet the late television personality's childhood friends in Mexia, Texas and gifting Dannielynn some of her mom's belongings, like the wedding dress she wore to marry J. Howard Marshall II in 1994.

"Anna should be remembered as this larger-than-life figure that was really a caring, giving person," Larry shared on 20/20 in February 2021. "A beautiful lady who loved her fans and loved her family."

But most importantly, Larry emphasized how much she would love the person Dannielynn has become. 

"You are funny, crazy smart, pretty and just about everything I could ever imagine," he wrote in Dannielynn's birthday tribute on Instagram in September. "Your Mom would be so proud of you, I sure am."

Read on to see how Dannielynn has honored Anna Nicole in her outfits each year at the Kentucky Derby.

The 17-year-old sports a Gianfranco Ferre dress once owned by Janet Jackson and purchased at Julien's Auctions while attending the Barnstable Brown Kentucky Derby Eve Gala in May 2024.

The 16-year-old steps out in style with her dad Larry Birkhead after paying tribute to her late mom with a fashion statement at the Barnstable Brown Kentucky Derby Eve Gala in May 2023.

Anna Nicole Smith's daughter, then 15, sports a colorful look as she poses with dad Larry Birkhead at the 2022 Kentucky Derby.

Larry and Dannielynn appear at the 2022 Barnstable-Brown Gala, a Kentucky Derby pre-party. Dannielynn is wearing the outfit that Janet Jackson wore to the 2003 Barnstable-Brown Gala. Larry said it was purchased in a Julien's Auction, with proceeds benefitting charity.

They're back! Dannielynn and dad Larryreturned to celebrate the Kentucky Derby with these corresponding looks a day before the annual event.

Masked up!

All smiles!

Dannielynn and Larry attend the 2019 Kentucky Derby. He tweeted, "Kentucky Derby time once again. Dannielynn looks pretty in pink in her dress by Junona and her Mom's hat from her unforgettable appearance at The Kentucky Derby in 2004 #KentuckyDerby2019."

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

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

Everything's coming up roses for the twosome!

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

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

Larry leads the way as Dannielynn smiles for the cameras.

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

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

Who needs a fascinator when you're this fabulous?

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