Kentucky Derby: Sarah Hyland, NeNe Leakes & More Of The Craziest Celeb Hats

We are off to the races as The 2021 Kentucky Derby is finally here! What makes this legendary sports event even more fabulous is the over the top hats that A-list stars have been wearing to it for years upon years.

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cynthia bailey
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There’s nothing quite like the fabulous, epic and crazy headwear people don at the Kentucky Derby! Although the event might be all about the horses, plenty of eyes are on the celebs who attend the annual race, and those who get in on the fun with incredible hats and fascinators. The 2021 race is happening today, on Saturday, May 1, but will be looking different due to COVID-19.

While the event will be happening in a smaller fashion, the three big celebrity galas have hit the pause button — including the The Barnstable-Brown Derby Eve Gala, held at Patrica Barnstable Brown‘s private Louisville home with her twin sister Priscilla Barnstable. “We’re just flabbergasted that we need to postpone our Derby Eve Gala fun for another year,” Patricia said to the Courier Journal about the news. While the parties will be in short supply, the Derby i still happening — and we’re looking back at some of the greatest celeb hat looks of all time.

The race at the Kentucky Derby only lasts a few minutes, but the fun and fashion goes on all day long. There’s not many opportunities for people to acceptably rock obnoxious hats in public, but the Derby is just the place, and celebs have always taken advantage of the chance to be totally out-there with their style. For instance, in 2014, Miranda Lambert rocked a stunning red dress, which she paired with a giant bow of the same color on the left side of her head. Keeping with the red theme, she added red heels and a matching lipstick!

Miranda Lambert
Miranda Lambert stuns at the 2014 Kentucky Derby. (Shutterstock)

Modern Family star Sarah Hyland also stunned on the carpet at the Kentucky Derby in 2019 when she donned a sleeveless white dress adorned with a colorful floral pattern. She matched the knee-length frock with simple black stiletto pumps, and allowed her incredible fascinator to take center stage. Her headwear featured a beautiful, deep red flower, and delicate mesh detailing which covered the left side of her face. It also featured two beige feathers which stuck out above the flower. So classy!

Sarah Hyland
‘Modern Family’ alum Sarah Hyland is seen attending the Kentucky Derby. (Shutterstock)

2020 was a tough year for the derby after multiple cancellations and rescheduled dates due to the pandemic. Churchill Downs Incorporated (CDI) announced its decision to reschedule the 146th Longines Kentucky Oaks and Kentucky Derby Presented by Woodford Reserve, in a March 17 press release. “The 146th Kentucky Derby will be rescheduled from May 2, 2020, to September 5, 2020, and the 146th Kentucky Oaks will be rescheduled from May 1, 2020, to September 4, 2020.” CDI’s CEO, Bill Carstanjen said that safety was his organization’s first priority.

“Throughout the rapid development of the COVID-19 pandemic, our first priority has been how to best protect the safety and health of our guests, team members and community,” Bill said. “As the situation evolved, we reached the difficult conclusion that we needed to reschedule. At no point did we ever consider canceling the Kentucky Derby.”

Click through the gallery above to see stars who’ve rocked epic hats to the Kentucky Derby.