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Fashion Rewind: Looking Back at the Best Styles from the Kentucky Derby Through the Years

The 2018 Kentucky Derby is scheduled to take place tomorrow at Churchill Downs in Louisville, Ky., with a parade of style hitting red carpets to watch the annual competition.

And in honor of the historic annual horse race, known for bringing out a range of celebs donning preppy Southern-inspired fashion, FN is taking a look back at some of the best moments through the years.

In 2006, R&B singer and actress Ashanti went for a curve-hugging floral dress and matching hat complete with flower-embellished silver and gold sandals. The starlet polished off her glamorous look with a pearl-drop necklace, earrings, a matching bracelet and ring and a tan leather clutch bag.

ashanti, kentucky derby
Ashanti wearing a printed curve-hugging dress and embellished sandals in 2006.
CREDIT: Rex Shutterstock

Serena Williams was also at Churchill Downs for the Derby in ’06, where she rocked a black and white ensemble for the occasion. The tennis champion wore a black feather-embellished hat with a white sundress and floral lace-up wedge sandals. Oversized frames, several eye-catching pieces of jewelry and a brown and white leather handbag pulled things together.

serena williams, kentucky derby 2006
Serena Williams attends the Kentucky Derby in 2006.
CREDIT: Rex Shutterstock

In 2008, “Breaking In” star Gabrielle Union wore a fluttery blue polka-dot dress featuring a ruffle-trim neckline and chunky black leather platform sandals. A black hat, hoop earrings and a black clutch bag topped off the look.

kentucky derby 2008, gabrielle union
Gabrielle Union at the Kentucky Derby in 2008.
CREDIT: Rex Shutterstock

In 2013, designer and former reality star Lauren Conrad made a fashion statement in a head-to-toe nude look consisting of a skintight polka-dot dress, platform round-toe patent leather pumps and a matching headpiece.

lauren conrad, kentucky derby 2013
Lauren Conrad at the Kentucky Derby in 2013.
CREDIT: Rex Shutterstock

For more celebrity looks at the Kentucky Derby through the years, check out the gallery.

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