Best Kentucky Derby Looks Over the Years

Flowers and dainty lace attached to the brim added a soft and feminine touch to this Derby spectator's outfit.

We barely recognized Jessica Simpson in this larger-than-life, wide-brimmed, floppy hat. But, the Texan effortlessly pulled off florals and head-to-toe pink at the track.

We wish we could have one in every color.

The Kentucky model and actress decided to go the more elegant route with her 2008 Derby look. Those are definitely not your mama's pearls and Sunday church hat.

LeeAnn Rimes not only won us over with her soul-stirring rendition of the National Anthem at the Derby, but her pretty floral dress and matching chic hat were also showstoppers.

The Little Rock native and former first daughter proved that there's always room for simple, even at the Kentucky Derby. We don't know who won the race that year, but the sparkling hat, subtle sheer overlay, and draping on Chelsea Clinton's gray dress deserved the day's top honor.

Jessica Simpson's little sister attended the big race in 2010 with then-husband Pete Wentz, dressed in a beautiful polka dot dress and matching platform sandals. We love the more sophisticated, demure hat here and her Southern nod to pearls.

Supermodel and Fort Lauderdale native Niki Taylor was all smiles, scoring major style points with a big golden bow topping her woven hat.

The country music star embraced her inner cowgirl at the 2012 Kentucky Derby, trading the pumps for cowboy boots to pair with her frilly, sweetheart dress.

Our resident Snow White and Tennessean Ginnifer Goodwin arrived in style and brights at the Kentucky Derby in 2012, donning a massive orange hat for the celebration.

Clearly, two is stylish company here. Country singer Luke Bryan was ever so dapper at the Derby, rocking a pastel blazer, complementary pocket square, and fedora, with his gorgeous wife Caroline by his side wearing a beautiful printed sheath dress and feathered hat.

We don't know what we're most impressed by here—the beautiful lace overlay on this attendee's dress, the ruffle detailing on her coat, or the sequined headpiece? Either way, it's clear that a couple who slays the Derby together, stays together. Bonus Southern style points for the matching mint juleps!

Who else but Miranda Lambert could've pulled off such a daring and bold ensemble? As only a Southern belle would do, the "More Like Her" singer stepped out in a signature red pout to match her red dress, fascinator, clutch, and satin pumps.

The American Idol winner, who grew up in Birmingham, Alabama, nailed this look, complete with a bow tie and appropriate 1920s style Skimmer Hat for the outdoor sporting event.

Clark Janell Davis was crowned Miss Kentucky in 2015, but we think the crowning glory here is the intricate fascinator hat she wore at the Derby. It's absolutely divine and Queen-approved.

Will Chase of former ABC drama series Nashville and singer-songwriter Ingrid Michaelson attended the Derby decked out in one of our favorite spring color combinations: cobalt blue and bright yellow. Michaelson's headpiece struck the perfect fashionable chord.

We saved the best for last. Because where else, other than the Kentucky Derby, would you expect to see a disco ball-inspired, cherry topper?