See the Best Dressed Stars Ever at the Kentucky Derby

The Kentucky Derby races to NBC and Peacock May 6. Take a look at Victoria Justice, Jessica Simpson and more celeb guests that dressed to impress.

By EOL Staff May 05, 2023 3:30 AMTags
Watch: Shailene Woodley & Aaron Rodgers Dress to Impress at Kentucky Derby

Hats off to these fashion icons.

Between Victoria Justice's chic pantsuit and Sarah Hyland's darling floral getup, there's no de-neigh-ing that celebs dress to the nines for the Kentucky Derby.

It's true—Derby fashion is such an important tradition, that stars even commission custom-made outfits. At the 2018 event, Black-ish actor Anthony Anderson wowed in a custom, canary-yellow suit. "This was specifically made for the Derby today," he told reporters at the time. "I may put it in a case and just have it in the family room." Needless to say, his look certainly brightened up our day.

This year, we're betting on even more unforgettable ensembles. After all, we can't be the only ones itching to dress up again in person or virtually!

The 149th Kentucky Derby is set to air Saturday, May 6, with coverage kicking off at 12 p.m. ET / 9 a.m. PT on NBC and Peacock. In addition to whimsical headwear, viewers won't want to miss Grammy winner Carly Pearce's National Anthem performance at the Churchill Downs Racetrack. 

Anna Nicole Smith's Daughter Dannielynn Birkhead's Kentucky Derby Days

In honor of this year's event, keep reading to see which celebrity guests of years past did not disappoint with their show-stopping lewks...

Flower Power

Before singing the National Anthem at the 2021 Kentucky Derby, Tori Kelly shows off her floral look including a bag from behno. 

Yin & Yang

Love is Blind hosts Vanessa and Nick Lachey have proven our hypothesis that they're style icons. 

Beige Beauty

Lauren Conrad stunned in a perfectly coordinated beige ensemble, hat and all.

Floral Femme

Modern Family star Sarah Hyland looked darling in a tea-length floral getup. 

Keeping Up With Couture

We object to how amazing lawyer-to-be Kim Kardashian looked in black and white at the 2009 Kentucky Derby. 

Heavenly Hair Pieces

Johnny Weir is a crowd pleaser on any carpet, but at the Kentucky Derby he made sure to go above and beyond.


At least Taylor Dayne didn't have to worry about the sun getting in her eyes.

Silky Dreams

Joey Fatone opted for a vibrant pattern to set the tone for the day in 2018,

Mix and Match

Chef Graham Elliot went all out for the event. Patterned jacket, white pants, and matching glass? Don't mind if we do!

Daddy Daughter

Dannielynn Birkhead and her dad are always a hit on the Kentucky Derby red carpet, and they stole the show with their pink and yellow frills.

Hats Off

President Donald Trump's ex-wife, Ivana Trump, showed off her whimsical hat. We also love her drop pearl earrings— it's all in the accessories.

Mint Dream

Golfer Rickie Fowler knew that when in doubt, always had some fun patterns with a mix of bright colors.

Lookin' Dapper

Johnny Knocksville showed up in a suit looking like a modern day Ferris Bueller. The stuntman opted for a slick suit and probably a few pranks.

So Subtle

Aisha Tyler knows how to steal focus, and when it came time for her to turn up at the Kentucky Derby, she made sure all eyes were on her.

Fit the Pattern

Joey Fatone wanted to make sure he was spotted from miles away in this patterned ensemble for the 2019 event.

Old School

Anthony Anderson was kicking it old school when he showed up to the Derby looking like he was straight out of an old western film.

Rockin' the Red Carpet

Kid Rock looked right at home with his cowboy boots and signature sunglasses look.

Crown & Gown

Natalie Zea nailed this black and red ensemble, and paired it with a faux crown. All hail the queen of the Kentucky Derby!

Pop of Color

Sometimes in order to fit in you've got to stand out. NeNe Leakes knew all too well how to get all eyes on her.

Talk of the Town

Country superstar Jennifer Nettles returned to her southern roots with the regal and fun outfit.

Blushing Beauties

It's not everyday you get to match with your dad on a red carpet, but these two have never disappointed while at the Kentucky Derby.

Statement Hat

Katie Couric went classy and chic with her flower details.

Bright Spot

Giada De Laurentiis wasn't afraid to show her wild side with this extravagant number.

Animal Connection

Cynthia Bailey switched things up by bringing out the animal prints.

Vision in White

Destiny's Child alum Michelle Williams stayed mysterious with this oversized hat obscuring half her face.

Wearing the Blues

This father daughter duo shined bright in their matching powder blue ensembles.

Pretty In Pink

Jessica Simpson was almost unrecognizable in this wide brimmed pink hat.

Matching Set

Richard and Tina Lawson opted for a moodier look and kept the mystery alive.

Hat Trick

Laila Ali went old school for her red ensemble with a feathery hat to boast.

Group Shot

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

View More Photos From Kentucky Derby's Most Memorable Fashion Moments Over the Years

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