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

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!

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.

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

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

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.

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

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.

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.

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

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.

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

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

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.

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

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.

Katie Couric went classy and chic with her flower details.

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

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

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

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

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

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

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

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

You’ve got to give it up for Victoria Justice who practically brought her own sun covering with this hat.

Now that’s what we call fashion!