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Kentucky Derby's Most Memorable Fashion Moments Over the Years

28 photos
May 03, 2025 3:18 AM
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Travis Kelce, 2024 Kentucky Derby
1/28
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.


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2/28
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.


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3/28
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.


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Stephen J. Cohen/Getty Images

Rachel Platton

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


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Michael Loccisano/Getty Images for Churchill Downs

Jack Harlow

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


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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. 


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7/28
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.


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8/28
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.


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AFF-USA/REX/Shutterstock

Taylor Dayne

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


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AFF-USA/REX/Shutterstock

Cynthia Bailey

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


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AFF-USA/Shutterstock

Dannielynn Birkhead & Larry Birkhead

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


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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.


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Michael Loccisano/Getty Images for Churchill Downs

Anthony Anderson

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


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Dia Dipasupil/Getty Images for Chruchill Downs

Joey Fatone

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


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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.


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Dia Dipasupil/Getty Images for Chruchill Downs

Laila Ali 

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


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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.


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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.


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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.


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Michael Loccisano/Getty Images for Churchill Downs

Victoria Justice

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


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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.


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Gustavo Caballero/Getty Images for Churchill Downs

Katie Couric

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


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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.


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24/28
Joey Foley/FilmMagic

Sarah Hyland

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


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