Fashion is in the eye of the beholder.
The Kentucky Derby kicks off on Saturday, Sept. 5! It is one of the biggest events in the equestrian world and this year's races will mark the 146th event. Every year, it is a breeding ground for great fashion and big risks.
Sometimes it pays off—staple Dannielynn Birkhead always delights—and other times celebs will go a little too over the top with their bold, colorful looks. We see you Joey Fatone! At the end of the day, it's all part of the fun of celebrating a day out to the course.
Luckily, we've rounded up the most OMG moments of pure fashion delight from the Kentucky Derby red carpet of years past. These celebrity looks did not disappoint—and these stars definitely gave it their all when it came to Southern glam and mega big hats they decided to rock. You've got to see it to believe it.
Scroll through the gallery below to see the most extravagant looks of the Kentucky Derby history!
Travis Kelce
The Kansas City Chiefs tight end's pinstriped suit for the 2024 Kentucky Derby was a total touchdown.
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.
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.
Rachel Platton
The singer sent big waves into motion with this floral look in 2023.
Jack Harlow
The rapper was riding in first class with this classy suit at the 2022 event.
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.
Michelle Williams
Fashionistas will be jumpin', jumpin with excitement over the Destiny's Child alum's floral dress for the 2019 derby.
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.
Taylor Dayne
Hats off to the "Love Will Lead You Back" singer's 2019 look.
Cynthia Bailey
The Real Housewives of Atlanta star donned a fabulous and fierce leopard-print dress in 2019.
Dannielynn Birkhead & Larry Birkhead
The father-daughter duo stole the show with their pink and yellow frills at the 2019 derby.
Jennifer Nettles
The country superstar returned to her southern roots with this lavender outfit and rosy fascinator for the 2019 Kentucky Derby.
Anthony Anderson
In 2018, the Black-ish star sported a dapper yellow suit.
Joey Fatone
The *NSYNC singer's vibrant suit jacket really did pop at the 2018 Kentucky Derby.
Tara Lipinski & Johnny Weir
In 2018, the Olympic figure skaters proved once again they never freeze up when it comes to fashion.
Laila Ali
The retired boxer's dress and hat for the 2018 derby were total knockouts.
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.
Aisha Tyler
The Criminal Minds actress rocked the red carpet with her pink floral dress and coordinating butterfly hat at the 2018 Kentucky Derby.
Penatonix
The group decided to embrace the solo look with each member wearing their own specific fashion to the 2018 event.
Victoria Justice
You could say the actress's look for the 2018 derby was victorious.
Giada De Laurentiis
The culinary star's dress for the 2017 Kentucky Derby was a true chef's kiss.
Katie Couric
The journalist went for classy and chic with her flower details at the 2017 derby.
Vanessa Lachey and Nick Lachey
While attending in 2015, the Love Is Blind hosts proved they aren't blind when it comes to style.
Sarah Hyland
The Modern Family actress dazzled in a tea-length floral getup in 2015.
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.
Kim Kardashian
No one can object to how great the lawyer-to-be looked in black and white at the 2009 Kentucky Derby.
Richard Lawson & Tina Knowles
The now-exes coordinated in black and white ensembles for the 2018 event.
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.
Now that's what we call fashion!