Trot on Over to See the Best Kentucky Derby Looks of All Time

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The 2025 Kentucky Derby will take place at Churchill Downs in Louisville May 3. But the event isn't just horseplay. We're tipping our hat to Travis Kelce, Jessica Simpson and more of the best looks.

Kentucky Derby 2023: Best Celebrity Fashion Moments

We’re not horsing around: It’s almost time for the 2025 Kentucky Derby.

The event's 151st outing will take place at Churchill Downs in Louisville, Kentucky May 3. And while viewers will be chomping at the bit to see which of the 20 steeds cross the finish line first, that's not the only reason we're struggling to hold our horses. Fans will also be saddling up to go through all the star-studded looks.

Because from the head-turning hats and the bouquet of floral prints to the dapper bow ties and the sharp suits, the fashion is anything but horseplay.

"Derby fashion is a celebration of culture and expression with each year serving as a showcase of communal creativity," Zanna Roberts Rassi said in an April 2 press release for Churchill Downs Racetrack. “Whether it's through striking colors, statement headpieces or fantasy frills—the first Saturday in May at Churchill Downs sets a new standard for fashion's influence on sports and culture."

And you can bet there will be celebrities at this year’s derby, too. Simone Biles will tell the jockeys to get ready as the "Riders Up" announcer, and Grace Potter will sing the national anthem. In fact, the three-time Grammy nominee has already been practicing her performance of "The Star-Spangled Banner" quite a bit—even when carpooling.

“When I’m picking up my kid, you can hear me going ‘and the rocket’s red glare’ in the car as I’m coming in," Grace, who shares 7-year-old Sagan with husband Eric Valentine, said on the April 29 episode of Southern Living’s podcast Biscuits & Jam. "They’re like, 'Oh, here comes Ms. Potter.'"

Fans can watch the daylong coverage of the Kentucky Derby starting May 3 at 12 p.m. EST on USA Network and then 2:30 p.m. EST on NBC—though the main race won’t take place until about 6:57 p.m. EST. And while the event has been dubbed the "most exciting two minutes in sports," the memories of the fashion can last much longer.

So grab your mint julep and scroll through the looks celebrities have worn to the derby throughout the years.

Silas Walker/Lexington Herald-Leader/Tribune News Service via Getty Images

Travis Kelce

The Kansas City Chiefs tight end's pinstriped suit for the 2024 Kentucky Derby was a total touchdown.

Michael Reaves/Getty Images

Wynonna Judd

For her national anthem performance at the 2024 derby, the Grammy winner wore an elegant white suit jacket with black trim and lace detailing—finishing her look with a coordinating tie and top hat.

Stephen J. Cohen/Getty Images

Patrick Mahomes & Brittany Mahomes

The Kansas City Chiefs quarterback and the KC Current co-owner scored some style points with their pastel outfits in 2023.

Stephen J. Cohen/Getty Images

Rachel Platton

The singer sent big waves into motion with this floral look in 2023.

Michael Loccisano/Getty Images for Churchill Downs

Jack Harlow

The rapper was riding in first class with this classy suit at the 2022 event.

Michael Hickey/Getty Images for Churchill Downs

Tori Kelly

Before singing the National Anthem at the 2021 Kentucky Derby, the "Should've Been Us" artist showed off her floral look including a bag from behno. 

Stephen Lovekin/REX/Shutterstock

Michelle Williams

Fashionistas will be jumpin', jumpin with excitement over the Destiny's Child alum's floral dress for the 2019 derby.

Stephen Lovekin/REX/Shutterstock

NeNe Leakes

Sometimes in order to fit in you've got to stand out, which the Real Housewives of Atlanta alum knew all too well when she attended the 2019 Kentucky Derby in her sunny yellow dress plus a flower- and butterfly-adorned hat.

AFF-USA/REX/Shutterstock

Taylor Dayne

Hats off to the "Love Will Lead You Back" singer's 2019 look.

AFF-USA/REX/Shutterstock

Cynthia Bailey

The Real Housewives of Atlanta star donned a fabulous and fierce leopard-print dress in 2019.

AFF-USA/Shutterstock

Dannielynn Birkhead & Larry Birkhead

The father-daughter duo stole the show with their pink and yellow frills at the 2019 derby.

Stephen Lovekin/REX/Shutterstock

Jennifer Nettles

The country superstar returned to her southern roots with this lavender outfit and rosy fascinator for the 2019 Kentucky Derby.

Michael Loccisano/Getty Images for Churchill Downs

Anthony Anderson

In 2018, the Black-ish star sported a dapper yellow suit.

Dia Dipasupil/Getty Images for Chruchill Downs

Joey Fatone

The *NSYNC singer's vibrant suit jacket really did pop at the 2018 Kentucky Derby.

Dia Dipasupil/Getty Images for Chruchill Downs

Tara Lipinski & Johnny Weir

In 2018, the Olympic figure skaters proved once again they never freeze up when it comes to fashion.

Dia Dipasupil/Getty Images for Chruchill Downs

Laila Ali 

The retired boxer's dress and hat for the 2018 derby were total knockouts.

Dia Dipasupil/Getty Images for Chruchill Downs

Graham Eliott

For the 2018 Kentucky Derby, the chef served up a red jacket, bold blue shirt and white pants—topping his ensemble with a hat, bow tie, pocket square and sneakers.

Dia Dipasupil/Getty Images for Chruchill Downs

Aisha Tyler

The Criminal Minds actress rocked the red carpet with her pink floral dress and coordinating butterfly hat at the 2018 Kentucky Derby.

Dia Dipasupil/Getty Images for Chruchill Downs

Penatonix

The group decided to embrace the solo look with each member wearing their own specific fashion to the 2018 event.

Michael Loccisano/Getty Images for Churchill Downs

Victoria Justice

You could say the actress's look for the 2018 derby was victorious.

Gustavo Caballero/Getty Images for Churchill Downs

Giada De Laurentiis 

The culinary star's dress for the 2017 Kentucky Derby was a true chef's kiss.

Gustavo Caballero/Getty Images for Churchill Downs

Katie Couric

The journalist went for classy and chic with her flower details at the 2017 derby.

Joey Foley/FilmMagic

Vanessa Lachey and Nick Lachey

While attending in 2015, the Love Is Blind hosts proved they aren't blind when it comes to style.

Joey Foley/FilmMagic

Sarah Hyland

The Modern Family actress dazzled in a tea-length floral getup in 2015.

Mike Coppola/Getty Images for Moet & Chandon

Lauren Conrad

We're coming clean and noting the Laguna Beach alum stunned in a perfectly coordinated beige ensemble—hat and all—at the 2013 derby.

Jeff Gentner/Getty Images

Kim Kardashian

No one can object to how great the lawyer-to-be looked in black and white at the 2009 Kentucky Derby. 

Michael Loccisano/Getty Images for Churchill Downs

Richard Lawson and Tina Lawson

The now-exes coordinated in black and white ensembles for the 2018 event.

AP Photo/Darron Cummings

Jessica Simpson

The singer's pink hat and floral dress for the 2004 Kentucky Derby were so good they may just take your breath away.

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