Dannielynn and her father Larry Birkhead made their annual appearance at the Barnstable-Brown Gala during the Kentucky Derby weeken

Dannielynn and Larry Birkhead. PHOTO: LARRY BIRKHEAD/INSTAGRAM

Larry Birkhead and his daughter Dannielynn made a stylish appearance at the Kentucky Derby festivities on Friday, May 3. The proud father shared snapshots of their outing on Instagram, showcasing their elegant attire as they headed to the Barnstable-Brown Gala, which marked the start of the Kentucky Derby weekend.

In the first image, the two sat beside each other sharing a seat while smiling for the camera. The photographer wore a gray suit set with a black tie as his daughter opted for an all-black look previously worn by Janet Jackson.

“Dannielynn is wearing her second @janetjackson outfit to the party that I got from Janet’s @juliens_auctions -charity auction,” he wrote of her attire.

According to Julien’s, the garment is a “Gianfranco Ferre black dress that’s knee-length in the front and floor-length in the back and features zippers all around.”

Birkhead concluded, “Looking forward to a fun Derby weekend with the newly graduated high school student!”

The daughter of the late Anna Nicole Smith lives a relatively private life year-round. However, each May, Dannielynn and Birkhead make it their mission to attend the Kentucky Derby together — a tradition they’ve had since Dannielynn was 3 years old.

Anna Nicole Smith, Dannielynn Birkhead. PASCAL LE SEGRETAIN/GETTY / MICHAEL LOCCISANO/GETTY

“Ahh The derby where you met her mama!!! I love that you’ve made it a tradition. She’s beautiful! You both look great. Congrats Danni! 🥹💞,” one person wrote in the Instagram comment section.

For the 2023 Kentucky Derby, the teen wore a sunflower print dress designed by Leo Lin while posing for photos with her father — who coordinated with similar colors.

Dannielynn Birkhead and Larry Birkhead, 2023 Kentucky Derby. LARRY BIRKHEAD/INSTAGRAM

Other than their annual father-daughter outings, the pair are also known to be supportive of one another via social media.

For Birkhead’s birthday in January, he joked about how his daughter snapped “really bad pictures” of him.

“#1-3) A friend took us to dinner for my birthday and Dannielynn continued her journey to take really bad pictures of me,” he began in his Instagram caption, alongside photos of himself and his daughter laughing over a meal.

And for Dannielynn’s birthday in September, Birkhead praised his daughter.

“Happy 17th Birthday Dannielynn! I am so proud of you in each and every way. Wishing you the best day ever!” he wrote. “You are funny, crazy smart, pretty and just about everything I could ever imagine. Your Mom would be so proud of you, I sure am.”

Before ending his post, Birkhead added, “Happy Birthday! Love Dad ❤️ By the way, when you asked me if you could live in my basement forever. I said yes, but I didn’t have the heart to tell you there aren’t any basements in Florida 😂 ❤️ #HappyBirthday 🎂.”

All Grown Up! See Anna Nicole Smith’s Daughter Dannielynn Birkhead Through the Years

Larry Birkhead and Anna Nicole Smith’s daughter has gone from tiny tot to little lady in her years at the Kentucky Derby and her rare public moments beyond

Dannielynn Birkhead and Larry Birkhead at the 2022 Kentucky Derby. PHOTO: MICHAEL LOCCISANO/GETTY

Anna Nicole Smith and Larry Birkhead’s daughter Dannielynn Birkhead turned 17 on Sept. 7, 2023, and though she has spent her life both in and out of the spotlight, as her father once said, it’s gone fast, regardless: “We went from diapers and teething to braces and sports bras overnight!”

Larry Birkhead has been quite private about his daughter Dannielynn’s daily life, but fans have had the privilege of watching her grow up, especially during their annual outings to the Kentucky Derby. Larry occasionally shares glimpses of their adventures together on social media, offering fans a peek into their close bond. Here’s a look at Dannielynn’s life through the years, including her stylish and sweet appearances at the Derby with her dad.

01of 19

2010

Dannielynn Birkhead and Larry Birkhead at the 2010 Kentucky Derby. MICHAEL HICKEY/WIREIMAGE

At just 3 years old, a pink-clad Dannielynn Birkhead made her Kentucky Derby debut with Dad.

02of 19

2011

Dannielynn Birkhead and Larry Birkhead at the 2011 Kentucky Derby. MICHAEL LOCCISANO/GETTY

“It’s tough raising a little girl without a mom,” Birkhead, at the Derby in 2011, told Steve Harvey in 2016. “You always want to make sure you’re doing the right things and a thing that a mom would choose that a dad might not choose.”

03of 19

2012

Dannielynn Birkhead and Larry Birkhead at the 2012 Kentucky Derby. MICHAEL LOCCISANO/GETTY

At the 2012 race, Dannielynn opted for her very first Derby-esque headpiece. Though Birkhead keeps his daughter out of the spotlight, the pair lives in rural Kentucky and make an annual trip to the horse race.

04of 19

2013

Dannielynn Birkhead and Larry Birkhead at the 2013 Kentucky Derby. MICHAEL LOCCISANO/GETTY

The father-daughter duo went to Churchill Downs in 2013 as Mary Poppins and Bert — parasol and all!

05of 19

2014

Dannielynn Birkhead and Larry Birkhead at the 2014 Kentucky Derby. STEPHEN J. COHEN/WIREIMAGE

“I look at her and she’s my everything,” Birkhead — with his daughter at the 2014 race — told Inside Edition. “She reminds me so much of her mom and as she gets older, and her features are changing, it’s just like having a little miniature Anna Nicole running around in so many ways.”

06of 19

2015

Dannielynn Birkhead and Larry Birkhead at the 2015 Kentucky Derby. NEILSON BARNARD/GETTY

In a February 2017 interview with 20/20, Birkhead said Dannielynn, at the Derby in 2015, is “fearless like her mom.”

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2016

Dannielynn Birkhead and Larry Birkhead at the 2016 Kentucky Derby. GUSTAVO CABALLERO/GETTY

“We went from diapers and teething to braces and sports bras overnight,” Birkhead told Wendy Williams in 2017. “It’s great and it’s a lot of work.”

08of 19

2017

Dannielynn Birkhead and Larry Birkhead at the 2017 Kentucky Derby. MICHAEL LOCCISANO/GETTY

For the duo’s eighth Derby, the proud pop and his 10-year-old coordinated in pink. Birkhead also took Dannielynn to the Barnstable-Brown Party, where he’d first met Anna Nicole Smith in 2003.

09of 19

2018

Dannielynn Birkhead and Larry Birkhead at the 2018 Kentucky Derby. DIA DIPASUPIL/GETTY IMAGE

Like previous years, Dannielynn was dressed to the nines at the 2018 Derby — this time wearing a white silk Southern belle gown with blue hydrangea appliqués from Lesy boutique. Her dad coordinated in a blue checkered suit from menswear designer Nick Graham.

10of 19

2019

Dannielynn Birkhead and Larry Birkhead at the 2019 Kentucky Derby. STEPHEN J. COHEN/WIREIMAGE

Dannielynn was in her brightest ensemble yet for the 2019 event, making an appearance at the Barnstable Brown Kentucky Derby Gala before the official kickoff of the horse race.

11of 19

2019

Dannielynn Birkhead and Larry Birkhead in 2019.

In June 2019, proud dad Larry shared three photos of his 12-year-old daughter celebrating her seventh-grade graduation.

“Surprised Dannielynn with @HamiltonMusical tickets for 7th grade graduation,” Birkhead captioned the sweet snaps. “I think she is happy!”

12of 19

2021

Dannielynn Birkhead in 2021. ABC 20/20/YOUTUBE

COVID-19 meant no appearance from the pair at the scaled-back 2020 Kentucky Derby, but fans got an even broader look into the Birkheads’ life in a February 2021 20/20 special that told Anna Nicole Smith’s story.

“Dannielynn’s a teenager now, and she doesn’t really know a ton of things about her mom,” Larry said in a voiceover on the trailer. “To be really honest, I didn’t know a whole lot about Anna — you know, her early years,” he added.

13of 19

2021

Dannielynn Birkhead in 2021. 2020/TWITTER

Part of the 20/20 special focused on Dannielynn seeing some of her mother’s possessions for the first time.

“She has a big heart like her mom had, I think she could appreciate these things,” Larry said of his daughter, then 14.

“When we talk about Anna Nicole, there were a lot of happy moments for her,” Larry said in the special. “There were a lot of highs before there were a lot of lows.”

“Anna should be remembered as this larger than life figure that was really a caring, giving person. A beautiful lady who loved her fans and loved her family,” he added.

14of 19

2021

Dannielynn Birkhead and Larry Birkhead at the 2021 Kentucky Derby. LARRY BIRKHEAD/INSTAGRAM

Though the father-daughter pair’s favorite Barnstable Brown Kentucky Derby Gala did not take place due to COVID-19, they still attended the Kentucky Derby in their best fashions.

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2022

Dannielynn attended the 2022 Barnstable Brown Gala in the same outfit Janet Jackson wore to the same event in 2003.

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2022

Dannielynn Birkhead and Larry Birkhead at the 2022 Kentucky Derby. MICHAEL LOCCISANO/GETTY FOR CHURCHILL DOWNS

And the next day, she and Dad got all dressed up again for the Kentucky Derby.

17of 19

2022

Dannielynn Birkhead and Larry Birkhead with Janet Jackson in 2022. LARRY BIRKHEAD/INSTAGRAM

Talk about a dream come true! The father-daughter pair met Janet Jackson backstage at the singer’s June 2022 concert in Cincinnati, Ohio.

“After hours of singing, dancing and sweating through the @cincymusicfest we got to hang with @janetjackson She killed it, managed to include all of her hits, sing and dance in the heat and still find time for two of her fans,” Larry wrote. “A great weekend. How cute is Janet 👀 ❤️?”

18of 19

2023

Dannielynn Birkhead and Larry Birkhead at the 2023 Kentucky Derby. LARRY BIRKHEAD/INSTAGRAM

The 16-year-old and her dad attended the 34th annual Barnstable Brown Kentucky Derby Eve Gala on May 5, 2023, where she wore a black tulle skirt and blouse featuring her mom’s photographs from her famous Guess campaign, accessorized with rhinestone shoes.

“She’s showing off her fashion sense but at the same time paying tribute to her mom,” Birkhead told PEOPLE just ahead of the annual gala.

19of 19

2023

Dannielynn Birkhead and Larry Birkhead at the 2023 Kentucky Derby. LARRY BIRKHEAD/INSTAGRAM

Dannielynn and her dad attended the 2023 Kentucky Derby together, where the teen wore a sunflower print dress designed by Leo Lin. She accessorized the look with a crystal necklace and bracelet from her mom’s archives.