Yahoo News The Kentucky Derby Has Attracted Many Big Celebrities Over the Years
While most of us opt to watch The Kentucky Derby from home or at a party with a mint julep in hand, some of your favorite celebrities have traveled to Churchill Downs on the first Saturday of May to take in the greatest two minutes in sports firsthand.
Just as they would on a movie premiere red carpet, these stars made sure to dress in their finest Derby duds, from eye-catching hats and pastel sundresses to bourbon-themed pocket squares. (Keep scrolling to see which actor brought that clever accessory!)
We rounded up 35 photos of celebrities at The Kentucky Derby over the past 20 years, from British royalty to NFL legends. We're eager to see who will show up next!
Patrick and Brittany Mahomes (2023)
Patrick and his wife, Brittany, posed for photos in the Paddock while sporting coordinating shades of pink and blue. After taking home the Super Bowl trophy earlier that year, the NFL star got to take on another sports milestone when he was tapped to deliver the iconic "Riders up!" call.
Jessica Simpson (2002)
In '02, Jessica sang along to "My Old Kentucky Home" before the race. The singer also attended the 2004 Derby with her then-husband Nick Lachey, which was filmed for their TV show, Newlyweds.
Queen Elizabeth II and Prince Philip (2007)
Queen Elizabeth II, who was notably passionate about horses, visited Kentucky five times during her royal reign. During her final visit, she stopped by Churchill Downs to take in the Run for the Roses. "She was at the track for three hours and everybody who met her said she was very kind," Greg Bush, the senior director of operations at Churchill Downs, told the Courier-Journal. And she was treated like, well, royalty.
Kim Kardashian (2009)
Instead of sporting the pastel color palette synonymous with the Derby, Kim opted for a black, white, and gray hat adorned with tulle and feathers. The reality star brought her mom, Kris Jenner, as her guest during her trip to Louisville.
Jack Harlow (2023)
The rapper and Louisville native loves The Kentucky Derby so much, he wrote a song about it! The music video for "Churchill Downs," which was released in 2022 and features a cameo from Drake, was shot on location and includes actual Derby footage.
Miranda Lambert (2011)
The country singer opted for a black fascinator instead of a hat for her 2011 Derby look. "I'm pretty much obsessed with the royal wedding and Kate Middleton so I figured I was going to go and channel that," she said in her Derby red carpet interview. The year before, Miranda took a group of friends to The Kentucky Derby for her bachelorette party.
Lauren Conrad (2013)
The Hills star opted for a monochromatic outfit made complete by a tulle topper. "I didn't win a single bet, but we sure had fun," she wrote in an Instagram post.
Serena Williams (2006)
The tennis legend accessorized her halter Derby dress with a pair of oversized sunglasses and a wide-brimmed hat trimmed with feathers.
Chris Pine (2023)
Chris looked dapper in a light blue blazer, which he accessorized with classic Wayfarer sunglasses and a patterned pocket square. The actor attended The Kentucky Derby with his father, fellow actor Robert Pine.
Brooke Shields (2005)
Many Derby style experts recommend letting your hat be the focal point of your outfit. We think Brooke absolutely nailed that advice with her eye-catching cobalt hat!
Tara Lipinski and Johnny Weir (2021)
This duo traded in their ice skates for elaborate Derby headwear. Tara accessorized her pale pink gown with a braided headpiece, while Johnny sported a hat adorned with the race's signature roses. A serve!
Guy Fieri (2012)
Guy is no stranger to the excitement of Derby Day: He told Louisville Business First that he even considers himself "an unofficial spokesman" for the race. He's also hosted Derby-themed events at his restaurant in Louisville, Guy Fieri's Smokehouse.
Maren Morris (2017)
The country singer paired her striped skirt with a chic black fascinator on the red carpet at the Barnstable Brown Gala, a star-studded charity event held the night before the Derby.
Ashton Kutcher (2012)
Ashton played into the Derby's preppy dress code with a bowtie, newsboy cap, and a pair of classic sunglasses. He was spotted chatting with Tom Brady and Miranda Lambert before the race.
Peyton and Eli Manning (2005)
Two of football's most famous brothers were spotted together at Churchill Downs in 2005. In 2023, Deadline reported that Peyton's production company is creating both a documentary and a scripted film about Rich Strike, the 2022 Derby longshot winner.
Gabrielle Union (2008)
In 2009, the actress told Essence that she loved her Derby look. "I wanted a really timeless, Hollywood-classic look when I did all of the Cadillac Records press," she said. "With this one, the hair came together, the makeup came together, and the dress was beautiful." We absolutely agree.
Giada De Laurentiis (2017)
The chef paired her Italian-inspired dress with a yellow hat for her first trip to the Derby. "The whole idea of the hats and the outfits and the energy and the adrenaline rush and the betting—I'm just looking forward to all of it!" she told the Lexington Herald-Leader. "I have no expectations. I just want to take it all in."
Angela Bassett (2014)
The actress showed off her white floral fascinator designed by a local milliner on the red carpet ahead of the 140th Kentucky Derby. Angela told the Courier-Journal that she keeps coming back to the Derby because of "the people and the tradition."
Aaron Rodgers (2016)
Aaron, pictured here celebrating after the 2016 race, is a Kentucky Derby staple. "There's not many things more exciting than the feeling, whether it's the first race of the day or the Kentucky Derby or the Oaks, when all of the horses get installed and they're off to get the job done," he told TwinSpires in 2021.
Bobby Flay (2022)
Bobby is not only a horse-racing fan, but also a successful racehorse owner. In 2016, his horse, Creator, won the Belmont Stakes. "The thing I love about horse racing is that for $2, you can have an opinion," he told Esquire. "It's such an inclusive sport in that way."
Zoe Saldana (2007)
The actress gave her classic white dress a pop of color with a blue wide-brimmed hat. Bonus points for the unique shape and ribbon-inspired fabric!
Smokey Robinson (2010)
Smokey and his wife, Francis, are red carpet staples at the Run for the Roses—they've been spotted at the Derby multiple times over the years. In a red carpet interview before the 2023 race, the Motown legend said that if he had a horse in the Derby, he'd name it after his wife. Aw!
Tom Brady (2011)
The NFL star, pictured here in 2011, is a perennial Derby attendee. He's been spotted with a slew of fellow football stars at various races over the years, including fellow quarterback Jimmy Garoppolo and former teammate Rob Gronkowski. In fact, Gronk told an ESPN reporter that his favorite off-field memory with Brady was seeing him take a shot of Fireball at the Derby, if only to see the look of "disgust" on his face.
Spike Lee (2006)
Spike and his wife, Tonia, posed for photos before the 132nd Kentucky Derby. The director, who is rarely seen without his signature caps, opted for a black-and-white, polka-dot newsboy number to match his white suit.
Josh Duhamel (2016)
Josh attended the Derby for the first time in 2016, where he told the Courier-Journal that he was intimidated by how well-dressed everyone was. "I've got a little mint julep pocket square," he said. You did just fine, Josh!
Rebecca Romijn and Jerry O'Connell (2010)
Jerry has been spotted at the Derby several times over the years, and in 2010, he brought Rebecca along for the ride. "Louisville is great," he told BloodHorse. "This city just really knows how to do it."
Usher (2006)
Usher has been spotted at Churchill Downs multiple times. For the 2006 race, he accessorized his gingham shirt with a black bowtie. Dapper!
Jeff Bridges (2017)
Jeff and his wife, Susan, posed with their betting slips in the grandstand. The actor even got to deliver the traditional "Riders up!" call before the race.
Kacey Musgraves (2017)
The country singer, pictured here with her then-husband Ruston Kelly, wore a devil horn-inspired headpiece to a pre-Derby gala.
Kate Upton (2016)
The model served as the Kentucky Oaks ambassador during the annual pre-race parade. On the eve of the Derby, she told the Courier-Journal that she was looking forward to not only getting gussied up for the race, but also seeing everyone else's creative outfits.
Josh Groban (2015)
The singer posed in a blue suit ahead of the 141st Kentucky Derby. In 2015, he became the seventh musician to sing the National Anthem before the race, after the tradition began in 2009.
Nicole Richie (2004)
Although Nicole's yellow pantsuit and pink ribbon fit the Derby's color palette, she still added the grungy flair she was famous for with a black fedora. The reality star's trip to Churchill Downs came just a month before the second season of her hit reality show, The Simple Life, premiered.
Sarah Hyland (2015)
The Modern Family star chose to pair her floral Derby dress with a deep red velvet fascinator topped with feathers and a veil. We love.
Gene Simmons (2007)
Gene's visit to Churchill Downs was immortalized in an episode of his reality show, Gene Simmons Family Jewels. In the episode, the KISS frontman not only crashed his wife's girls' trip to Louisville, but was dismayed when she bet $100,000 on a horse. (We're guessing that's not what his thumbs-up was for.)
Ian Somerhalder (2011)
The Vampire Diaries star took to social media to share his excitement ahead of the 2011 Kentucky Derby. "On my way to The Kentucky Derby to hang with my old man and soak in some soon-to-be Kentucky rain...time with parental(s) is important," he tweeted. How sweet.
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