40 Celebrity Kentucky Derby Looks Over the Years

40 Photos of Celebrities Dressed to the Nines at The Kentucky Derby Over the Years
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40 Photos of Celebrities Dressed to the Nines at The Kentucky Derby Over the Years
From British royalty to NFL legends.
By Madison McGee Updated: May 6, 2024
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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 40 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!
Travis Kelce (2024)
LEANDRO LOZADA // Getty Images
It's no surprise that all eyes were on the Kansas City Chiefs star this year, as he was spotted celebrating his winning bet in the stands in this dapper outfit. Here's hoping he brings Taylor Swift next year!
Patrick and Brittany Mahomes (2023)
Rob Carr // Getty Images
Speaking of the Chiefs, a year prior, 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 Kansas City Chiefs star got to take on another sports milestone when he was tapped to deliver the iconic "Riders up!" call .
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Jessica Simpson (2002)
John Simpson // Getty Images
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 .
Martha Stewart (2024)
Jeff Schear // Getty Images
Ahead of the 150th Run for the Roses, Martha delivered the " Riders up !" call. The media mogul caused quite the stir with Derby viewers on social media when she nearly said "Connecticut" instead of "Kentucky," but we think she recovered quite well from the potential flub!
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Queen Elizabeth II and Prince Philip (2007)
TIMOTHY A. CLARY // Getty Images
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.
Thomas Rhett and Lauren Akins (2024)
Daniel Boczarski // Getty Images
From Thomas's pastel shirt to Lauren's floral fascinator, these Derby first-timers absolutely aced the dress code! Ahead of the race, the couple told NBC Sports that they enjoyed getting to learn behind the scenes details about horse racing. "It's amazing how you can know nothing about the horses or the names until right before the race, and then all of a sudden, you're the biggest fan of number 4 you've ever been in your life," Thomas said.
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Kim Kardashian (2009)
Jason Kempin // Getty Images
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.
Jimmy Fallon (2024)
Icon Sportswire // Getty Images
The late night star tried his hand at mixing patterns by pairing his purple and white-striped shirt with a polka dot tie.
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Jack Harlow (2023)
Jeff Schear // Getty Images
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.
Wynonna Judd (2024)
Rob Carr // Getty Images
The songstress waved to the crowd after performing the National Anthem ahead of the race. The Kentucky native told the Courier-Journal that performing in her home state was an honor, saying, "Tradition is a huge word in our family, and as dysfunctional as we are, we somehow managed to have faith and it's because of our Southern roots."
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Miranda Lambert (2011)
Theo Wargo // Getty Images
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)
Stephen Lovekin // Getty Images
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 .
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Serena Williams (2006)
Paul Hawthorne // Getty Images
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)
Stephen J. Cohen // Getty Images
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.
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Brooke Shields (2005)
Jeff Gentner // Getty Images
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)
Icon Sports Wire // Getty Images
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!
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Guy Fieri (2012)
Rob Carr // Getty Images
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)
Michael Hickey // Getty Images
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.
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Ashton Kutcher (2012)
Stephen J. Cohen // Getty Images
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 befo…

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