See the Most OMG Fashion Moments From the Kentucky Derby Over the Years

The Kentucky Derby always brings out the most outrageous fashion moments for celebrities around the globe! E! has compiled the most fun outfits from over the years.

By Vannessa Jackson Sep 05, 2020 1:00 PMTags
Watch: E! Style Collective's Best Beauty and Fashion Moments

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.

OMG Red Carpet Fashion Over the Last 30 Years

Scroll through the gallery below to see the most extravagant looks of the Kentucky Derby history!

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

Now that's what we call fashion!

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