Anna Nicole Smith’s Daughter Dannielynn, 16, Enjoys 2023 Kentucky Derby with Dad Larry Birkhead

Dannielynn Birkhead and dad Larry Birkhead are enjoying an exciting day at the 2023 Kentucky Derby!

On Saturday, the 16-year-old daughter of the late Anna Nicole Smith attended the 149th annual event with dad Larry, 50.

Dannielynn wore a sunflower print dress, designed by Leo Lin, which she accessorized with a crystal necklace and bracelet from her mom’s archives. “To be honest, the dress was so big I had to drive it from Florida, because it was too big to go on the plane and check it in. So this was a full-on production,” Larry tells PEOPLE.

For his part, the photographer wore a light blue suit that complimented his daughter’s dress. He completed the look with a yellow tie and handkerchief, as well as a sunflower pinned to his lapel.

In an Instagram post, Larry shared photos of himself and Dannielynn posing with Richie Sambora, who gave the teenager a guitar lesson. “Rockin’ the rest of @kentuckyderby … with Richie Sambora and Dannielynn,” he captioned the post. “Richie graciously made good on his offer to give Dannielynn a private guitar lesson and spent a ton of time giving her confidence building tips and mastering the art of playing the guitar. Great guy!”

Larry added: “Dannielynn played a little @janetjackson ‘Black Cat’ for him. Now off to the @kentuckyderby after the Barnstable-Brown Gala last night.”

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Dannielynn and Larry attend the Kentucky Derby each year. The annual horse racing event is held in Louisville, Kentucky, at the Churchill Downs racetrack on the first Saturday in May. They had previously attended the Barnstable Brown Gala on Friday night, which benefits the Barnstable Brown Diabetes Center at the University of Kentucky.

Now that their appearance has become a tradition, Larry tells PEOPLE, “The stakes are always high on these outfits. People come to me and ask, ‘What is Dannielynn wearing? Are you going to match?’ The problem is the dresses keep getting more expensive!”

Larry added that he has saved every outfit that his daughter has ever worn to the Derby. “There’s a whole storage bin devoted to all of her Derby dresses from when she was a baby,” he says. “And everything she has of her mom’s is cataloged in storage, with photos of the event where she wore it. So someday, she can give them to her kids if she wants to.”

As Dannielynn finishes her junior year of high school, Larry says, “I’m super protective of her. She’s a really good kid. And hope I had a little bit to do with that.”

“But this is our own big event. Our Met Gala!” he adds with a laugh. “The one event we go to every year because she’s not ‘out there’ in public.”

This year marks the 20th anniversary of when Larry first met Anna Nicole at the annual Barnstable Brown Gala, which he was sent to cover as a young photographer. “It’s great to be part of something that changed my life in so many ways,” he says.

“I think her mom would be proud,” he adds. “She might tell me I should have dressed her in more pink — but I think she’d be happy. That she is the young lady she turned out to be.”

Last year, Dannielynn celebrated her 16th birthday and Larry honored his not-so-little girl with a sweet tribute.

“Dannielynn is such a great kid and she makes me so proud every day,” he told PEOPLE at the time. “I can’t believe she is old enough to drive! It seems like yesterday I was pushing her in a toy car!”

The proud dad also posted a heartfelt message to his daughter on Instagram alongside a collage of images of Dannielynn through the years.

“Sixteen years ago my beautiful baby was born. That’s if you want to feel really old,” he teased. “Many people thought the odds were stacked against you, but maybe that was geared more towards me than you. Through tragedy, turmoil and a couple of baby tantrums-today you shine bright and are so accomplished. So proud to be your Dad!”

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Birkhead also shared a story about telling his daughter “what a great baby she was when she born.”

“She shot back in true Dannielynn style … ‘How do you know you weren’t even there?’ ???? Ouch,” he shared. “I told her ‘maybe not, but I have been there every day since I brought you home.’ ”

“It’s been a wild ride and Dannielynn has brought joy and laughter to my life. Stay off your local roads because Dannielynn is 16! Happy Birthday ❤️ Rock on ???? Mom is looking down! ????,” he concluded the post.

One of the photos included in the collage showed an infant Dannielynn being kissed by her late mother, who died in 2007 when Dannielynn was just 5 months old.