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  4. Best Kentucky Derby Looks Over the Years

Best Kentucky Derby Looks Over the Years

Southern Living May 2021 Cover
By Southern Living Editors
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Kentucky Derby
Credit: Jeff Haynes/Getty Images

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.  

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2002: Petal Power

Kentucky Derby Hat
Credit: Photo: Matthew Stockman/Getty Images

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

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2004: Pretty in Pink

Jessica Simpson
Credit: Photo: Getty Images

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.

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2006: Hats & Heels

Kentucky Derby
Credit: Jeff Haynes/Getty Images

We wish we could have one in every color.

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2008: All Dressed Up With Somewhere to Go

Molly Sims at the Kentucky Derby
Credit: Photo: Jason Kempin/Getty Images

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.

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2009: In Full Bloom

LeeAnn Rimes at the Kentucky Derby
Credit: Photo: Jason Kempin/Getty Images

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.

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2010: Sense & Simplicity

Chelsea Clinton at the Kentucky Derby
Credit: Photo: Jason Kempin/Getty Images

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.

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2010: Seeing Spots

Ashlee Simpson at the Kentucky Derby
Credit: Photo: Stephen J. Cohen/Getty Images

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.

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2011: A Timeless Embellishment

Niki Taylor Kentucky Derby
Credit: Photo: Michael Loccisano/Getty Images

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

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2012: Boots Made for Walkin'

Miranda Lambert at the Kentucky Derby
Credit: Photo: Getty Images

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.

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2012: Once Upon a Beauty

Gennifer Goodwin at the Kentucky Derby
Credit: Photo: Michael Loccisano/Getty Images

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.

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2013: Prints & Pastels

Luke Bryan at the Kentucky Derby
Credit: Photo: Mike Coppola/Getty Images

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.

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2014: A Chic Pair

Red and Black Couple at the Kentucky Derby
Credit: Photo: Icon Sports Wire/Getty Images

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!

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2014: Sizzling in Red

Miranda Lambert at the Kentucky Derby
Credit: Photo: Joe Imel/AP Photo

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.

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2015: All Tied Up

Ruben Studdard Kentucky Derby
Credit: Photo: Tasos Katopodis/Getty Images

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.

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2015: Hat's Off to Miss Kentucky

Clark Davis at the Kentucky Derby
Credit: Photo: Gustavo Caballero/Getty Images

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.

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2016: Singing the Blues

Will Chase at Kentucky Derby
Credit: Photo: Frazer Harrison/Getty Images

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.

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2016: Not For the Shy Wallflower

2016 Kentucky Derby
Credit: Photo: Getty Images

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?

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    Everything in This Slideshow

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    1 of 17 2002: Petal Power
    2 of 17 2004: Pretty in Pink
    3 of 17 2006: Hats & Heels
    4 of 17 2008: All Dressed Up With Somewhere to Go
    5 of 17 2009: In Full Bloom
    6 of 17 2010: Sense & Simplicity
    7 of 17 2010: Seeing Spots
    8 of 17 2011: A Timeless Embellishment
    9 of 17 2012: Boots Made for Walkin'
    10 of 17 2012: Once Upon a Beauty
    11 of 17 2013: Prints & Pastels
    12 of 17 2014: A Chic Pair
    13 of 17 2014: Sizzling in Red
    14 of 17 2015: All Tied Up
    15 of 17 2015: Hat's Off to Miss Kentucky
    16 of 17 2016: Singing the Blues
    17 of 17 2016: Not For the Shy Wallflower

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