Anna Nicole Smith's daughter and her dad make their annual Kentucky Derby trip: See their outfits through the years

For the late Anna Nicole Smith’s 18-year-old daughter, Dannielynn Birkhead, the Kentucky Derby is a family tradition.

Dannielynn gets all dressed up to attend the fashion-forward horse race with her father, Larry Birkhead. The tradition started in 2010 when she was just 3 years old, and posts of the day have become fan favorites.

This year, Dannielynn and her dad kicked off Derby weekend in style. In an Instagram post on Friday, May 2, Larry Birkhead shared a series of photos of him and his daughter together at 2025 Barnstable Brown Gala.

In caption of his post, Larry revealed that his daughter was wearing the same evening gown that her mother, Anna Nicole Smith, wore 21 years ago when she attended the same gala.

“Life full circle,” he captioned the post. “She said she chose the dress because it was her Mom’s and ‘super cool.’”

In a 2022 interview with the Courier Journal, Larry Birkhead explained why it means so much for him and his daughter to go to the Kentucky Derby together.

“It’s our ‘one day a year’ outing that we do publicly,” he said. “And I think you guys probably can take pictures and watch her grow from just this event … there’s a lot of people that are interested in things because of her mother, and I don’t let her fall into that. I just say, ‘Hey, let’s do one thing a year (and) let people see how you are.’”

Dannielynn was only five months old when Smith died in February 2007 after accidentally overdosing on prescription drugs. Five different men claimed to be Dannielynn’s father, but after a DNA test, Larry was legally designated as her father.

Dannielynn spent a relatively private childhood with Larry in their Kentucky home. But the father-daughter duo step into the spotlight on this one special day.

Let’s look back on Dannielynn and her dad at the Kentucky Derby through the years.

2010

Larry Birkead brought his daughter to the Kentucky Derby when she was 3 years old.

Dressed all in pink, Dannielynn looked thrilled by the cameras … and reassured by having her father nearby.

2011

Dannielynn sipped her kid’s drink like a lady when she attended the festivities in 2011, wearing a fun animal-print dress.

2012

Dressed in sunshine yellow at the 138th Kentucky Derby, Dannielynn sweetly gave her dad a giant smooch. Of course, her cute cow puppet is along for the ride.

2013

Is there anything sweeter than Larry and Dannielynn dressed up as Bert and Mary Poppins for the Kentucky Derby? After all, both feature a horse race!

2014

The family tradition continued to bloom when Dannielynn was 7. The floral bodice, tulle skirt and butterfly shoes signal her creativity. Larry sweetly echoes his daughter’s color choices in his striped tie.

2015

From bright colors to pastels, Dannielynn sports a slightly more grown-up look in 2015. Doing a complete 180 from last year, she wore a very demure pale pink dress and carried a sequin purse with flowers on it.

2016

An updo seems perfectly fitting for this elegant young lady who is wearing a light grey dress with pink flowers. With a grey suit, pink shirt and jaunty tie, Larry matches her exactly.

2017

Stunning as ever at the age of 10, Dannielynn looks like a perfect English rose in a pink dress with matching fascinator.

2018

Dannielynn and Larry change up their color palette by switching to blues in 2018. Just as she did last year, Dannielynn wore a fit-and-flare dress with a 1950s silhouette. Larry looks like the perfect parental escort in plaid.

2019

The pair switched back to bubble gum pink in 2019. Dannielynn looked right at home on the red carpet.

2020

The Triple Crown event was postponed in 2020 due to COVID-19. It was ultimately held in September without any spectators, so Dannielynn and Larry had to sit this one out. 

2021

In their return to the race in 2021, Dannielynn wore a rhinestone face mask that perfectly coordinated with her JOVANI suit. 

“She cleaned out the chocolate brownies, ice cream and nachos while at the same time critiquing my outfit,” Larry wrote on Instagram of his then 14-year-old daughter.

2022

Dannielynn was all color and joy in 2022, while Larry’s neutrals really let her grab the spotlight.

Along with two photos posing with his daughter, Larry posted an old snap of Smith giving her best pout for the camera on Instagram.

“Saw this pic of Anna and thought Dannielynn looked like her twin!” he added in the caption.

2023

The 2023 Kentucky Derby marked a special year for Larry, as it was his 20th anniversary of meeting Smith.

At the Barnstable Brown Derby Eve Gala, Dannielynn paid tribute to her mom by wearing a long-sleeved black and white top printed with a pattern of photos of Smith from her famous Guess campaign. Larry’s tie included the same print of Smith from his daughter’s shirt.

At the Derby itself, Dannielynn’s fashion sense was in full bloom with her flower-themed gown. Dad Larry Birkhead, as always, matched his look to hers.

2024

Last year, Larry detailed his Kentucky Derby weekend on social media. Dannielynn wore a bright red dress with puffy sleeves and a matching feathered headpiece. Larry shared that the ensemble was “inspired by her favorite character Hino Eiji, Kamen Rider OOO TaJaDor combo.”

He added, “Hey whatever works, just trying to spend a little quality time as this weekend of traditions come to a close…”

2025

This year, Dannielynn decided to pay tribute to her mother when she attended the annual Barnstable Brown Gala on the eve of the Kentucky Derby with her dad.

For the gala, she wore the same dress that her mother wore 21 years ago when she attended the same event.

“Life full circle,” Larry Birkhead captioned the post. “She said she chose the dress because it was her Mom’s and ‘super cool.’”