It’s time to awaken your inner Southern Belle and make your way to the 145th Kentucky Derby at Churchill Downs. The first Saturday in May brings 170,000 people to Louisville, Kentucky for races, fun and fashion. The Derby offers a unique opportunity to get dressed to the nines for a sporting event, turning a two-minute gallop into a day known for glamorous outfits and a profusion of over-the-top headwear.

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Hats have been the quintessential fashion item at the Kentucky Derby for most of its history, although the extravagant flourishes now associated with the Derby only became popular in the sixties. Whether you’re a celeb walking the Red Carpet in a designer creation, or a resourceful DIY hatter, what you wear above the shoulders should be the focus of your outfit. There are no rules when it comes to your Derby hat – as long as it’s comfortable and turns heads as you breeze past, you’re doing it right! Feathers, bows and flowers are always popular in the boxes, but down at the Churchill Downs Infield, you will see all sorts of innovative designs and oodles of humor.

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Last year marked the first time that a featured hat maker was selected to be involved in the official Derby festivities. Milliner to the Stars, Christine A. Moore already has a long history of creating hats specifically for horse racing events, so her creations are well-known and loved by those who appreciate the difference a custom made hat can make to your look. Christine’s Spring Collection features compact fascinators and exotically colored wide-brimmed hats, expertly trimmed with oversized, hand-painted silk flowers. You don’t need to be famous to show off one of Christine’s elegant pieces but – wearing one in the Kentucky Derby hat parade – you will undoubtedly feel like you are!

Whether you choose your dress first and then have a hat specially designed to complement your outfit, or find the perfect hat first, there are a couple of things to bear in mind. The Derby is primarily an outdoor event, and the Spring weather can be unpredictable. It’s best to dress in layers even if you’re spending most of the day in the seated areas. It can be a long day at the races – make sure your heels offer style as well as support to get you through all the events and down to the Winners’ Circle.

This is one event where the gents get to dress up too. Blazers in bright, fun prints with bow ties or neckties and smart-casual trousers will make sure you stand out in the crowd. Appointed “official style” of the Kentucky Derby, Vineyard Vines, has an excellent selection of Derby Day extravagance for everyone.

Place your bets, sip your Mint Julep, and cheer those colts and fillies to the finish!