Giddy up: The Kentucky Derby is back!
The event, which takes place at the Churchill Downs racetrack in Louisville, Kentucky, has a star-studded history packed with over-the-top style. However, amid the coronavirus pandemic, the 2020 race plans were postponed due to health concerns. Instead of the traditional three charity galas and a red carpet for Hollywood’s biggest stars, racing fans had to watch the equestrians jockey from a safe distance when the race returned in May 2021.
There have certainly been some pretty floral frocks and gorgeous suits worn to the event, but the Kentucky Derby is really all about the accessories. With that in mind, we’ve decided to take a trip down memory lane and look back at the best, wildest and most absurd headwear stars have worn.
Five years later, Kim Kardashian attended the Kentucky Derby. She kept her outfit on the simple side, but served up some glamour with an abstract gray hat that’s since gone down in fashion history.
When the 2013 race rolled around, Lauren Conrad stole the show, rocking a monochromatic ensemble. She paired her sweet polka dot dress with a linen and tulle headpiece that had a girly and feminine feel.
Kendra Wilkinson was another standout, taking a detour from the traditional flower-printed sundresses and bright colors. Instead, she opted for a sleek white blouse and black trousers. As for her headwear? She donned a wide-brimmed hat with feather embellishments.
But not all stars go for a simple or traditional headpiece. Some take risks with their Kentucky Derby accessories.
For example, in 2015, Sarah Hyland paired her floral-print midi dress with a burgundy fascinator that was nothing if not unique. The topper featured red mesh, a velvet flower and a few bird feathers.
Another wild one? Michelle Williams’ over-the-top blush-and-blue topper, which had large tulle and lace detailing, at the 2019 Kentucky Derby.
From Jessica Simpson in 2004 to Giada De Laurentiis in 2017 and everyone in between, keep scrolling to check out the most memorable Kentucky Derby headpieces: