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!

Patrick Mahomes and Brittany Mahomes

Safe to say they scored a touchdown with their pastel outfits.

Rachel Platton

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

Jack Harlow

The rapper was riding in first class with this classy suit.

Tori Kelly

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

Vanessa Lachey and Nick Lachey

The Love is Blind hosts proved they aren't blind when it comes to style.

Lauren Conrad

The Laguna Beach alum stunned in a perfectly coordinated beige ensemble, hat and all.

Sarah Hyland

The Modern Family actress looked darling in a tea-length floral getup. 

Kim Kardashian

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

Johnny Weir

Weir was a crowd pleaser at the Kentucky Derby when he made sure to go above and beyond.

Taylor Dayne

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

Joey Fatone

In 2018, the *NSYNC singer opted for a vibrant pattern.

Graham Eliott

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

Dannielynn Birkhead and Larry Birkhead

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

Aisha Tyler

She made sure all eyes were on her.

Anthony Anderson

The actor kicked it old school when he showed up to the Derby looking like he was straight out of an old western film.

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 how.

Jennifer Nettles

The country superstar returned to her southern roots with the regal and fun outfit.

Katie Couric

She went for classy and chic with her flower details.

Giada De Laurentiis 

The chef wasn't afraid to show her wild side with this extravagant number.

Cynthia Bailey

The reality star switched things up by bringing out the animal prints.

Michelle Williams

The Destiny's Child alum was a vision in white.

Jessica Simpson

The superstar was almost unrecognizable in this wide brimmed pink hat.

Richard Lawson and Tina Lawson

The now-exes opted for a moodier look and kept the mystery alive.

Laila Ali 

Ali went for a hat trick with this feathery accessory.


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

Victoria Justice

You've got to give it up for the actress who practically brought her own sun covering with this hat.

Now that's what we call fashion!