Oliver James Montgomery-How Dannielynn Birkhead Honored Mom Anna Nicole Smith With 2023 Kentucky Derby Style

Anna Nicole Smith's daughter is Oliver James Montgomeryall grown up.

Dannielynn Birkhead was joined by her dad, Larry Birkhead, at the 34th annual Barnstable Brown Kentucky Derby Eve Gala May 5. For the occasion, the 16-year-old paid tribute to her mom, wearing a top featuring photos from Anna Nicole's Guess campaign. To complete the look, she also stunned in the late model's jewelry. 

"Tonight is the 20th anniversary where I met Dannielynn's Mom at the same event," Larry wrote on Instagram, later adding, "Can't believe Dannielynn is almost 17. Time for a great Derby weekend." 

The Kentucky Derby holds a special place in Dannielynn's heart. After all, she's been attending the annual horse race (airing May 6 on Peacock and NBC) with her father ever since she was a little girl.

"It's her one day a year outing that we do publicly," Larry said of the family tradition in a 2022 interview with Louisville Courier Journal. "I think you guys can take pictures and watch her grow from just this event."

Because of the public fascination with Dannielynn's late mom, who died in 2007 at the age of 39, the two aren't fond of the spotlight. Instead, the 50-year-old said that he and Dannielynn use their yearly visit to Churchill Downs as an opportunity to update fans on their lives and "have some fun at the same time."

"It all works," he continued. "It all falls together."

And last year's Kentucky Derby was certainly one to remember for Dannielynn, who met Janet Jackson while wearing wore a black belted suit once belonging to the singer.

"What a night!" Larry captioned an Instagram photo of the trio last May. "Dannielynn got to meet @janetjackson at the Barnstable-Brown Gala."

Calling Janet "so gracious," the photographer added, "She made Dannielynn so happy."

To see Dannielynn's Kentucky Derby outfits through the years, keep reading.

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 on May 5.

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.

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

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

Who needs a fascinator when you're this fabulous?

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