What to Wear When Watching the Kentucky Derby

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Jet-setting across the seven seas, or simply swapping neighborhood spots, What To Wear When is your weekly column for shopping inspiration.

The first Monday in May might belong to the Met Gala, but the first Saturday in May is reserved for sipping mint juleps, wearing elaborate hats, and placing bets—all of which will take place at the legendary Churchill Downs Racetrack in Louisville, Kentucky. Dubbed “The Run for the Roses” (or, alternatively, “The Fastest Two Minutes in Sports”), the Kentucky Derby is one of the longest-running annual sports events in American history, having taken place every year since 1875. In fact, it even took place throughout the Great Depression and both World Wars. The Olympics, and practically every other season of professional sports, did not.

Naturally, the Kentucky Derby, which is just one out of three different races horses must win in order to be awarded the renowned Triple Crown, draws tons of celebrities and socialites from around the globe. Queen Elizabeth II even visited in 2007, and you’d be hard-pressed to find an A-lister who hasn’t made an appearance once or twice at the iconic stakes race. Whether you’ve snagged a spot among the deep-pocketed on Millionaire’s Row (lucky you), plan to party in the infield, or watch from your television, CR has you covered on the sartorial front.

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