Best Kentucky Derby Looks Over the Years
The Kentucky Derby is well-regarded in the South as the most exciting two minutes in sports. Not only is it one of the most popular horse races in the country, with crowds flocking to Louisville, Kentucky, it's also one of the most stylish events.(Plus, refreshing mint julep required.) Every year, we wait with baited breath to see Southern belles and gents pull out all the stops for their race-day ensembles and weekend party wear. In celebration of the Kentucky Derby, here are some of the most attention-grabbing dresses, suits, and headwear our favorite Southern celebrities and infield attendees have sported over the years, starting from the early 2000s to today. Cue major closet envy.
2002: Petal Power
Flowers and dainty lace attached to the brim added a soft and feminine touch to this Derby spectator's outfit.
2004: Pretty in Pink
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.
2006: Hats & Heels
We wish we could have one in every color.
2008: All Dressed Up With Somewhere to Go
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.
2009: In Full Bloom
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.
2010: Sense & Simplicity
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.
2010: Seeing Spots
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.
2011: A Timeless Embellishment
Supermodel and Fort Lauderdale native Niki Taylor was all smiles, scoring major style points with a big golden bow topping her woven hat.
2012: Boots Made for Walkin'
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.
DIY Derby Hat
Want a big, beautiful hat without the Derby price tag? Try making your own with fresh blooms.
2012: Once Upon a Beauty
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.
2013: Prints & Pastels
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.
2014: A Chic Pair
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!
2014: Sizzling in Red
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.
2015: All Tied Up
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.
2015: Hat's Off to Miss Kentucky
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.
2016: Singing the Blues
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.
2016: Not For the Shy Wallflower
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?