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Hats on and Off at the 150th Kentucky Derby

America’s most famous horse race may be celebrating a milestone this year, but the hats are the real stars of the show.

a woman in the stand wears a pastel pink large sun hat with decorative fuscai flowers.
A day of millinery delight filled blooms and brims.

There are many associations that come to mind with the Kentucky Derby. Horses, naturally. Mint juleps too. But to be a true participant in the Derby spectacle, one needs a proper Derby hat.

The tradition for wearing eye-catching attire to America’s most famous horse race began in the 1870s. The founder of the Kentucky Derby, Meriwether Lewis Clark Jr., was inspired by the fashionable dress codes at events like Ascot in Britain and Paris’s Grand Prix. Creating his own, he figured, would transform his racetrack from a place of ill-repute to one for well-heeled high society.

On a sunny spring Monday in 1875, more than 10,000 spectators attended the first Kentucky Derby and The New York Times reported on the fashion as well as the racing, noting that “the grandstand was thronged by a brilliant assemblage of ladies and gentlemen.” His plan worked, and this collective passion for horses, gambling and partying — even in smart seersucker suits or a spectacular feathered fascinator — has endured as a cornerstone of the Derby to this day.

This year marked the 150th running of the race at Churchill Downs, won this year by Mystik Dan in a photo finish. As expected nobody held back both on and off the track, from wide-brimmed styles adorned with spring florals and soft feathers paired with tasteful pastel-colored dresses to jockey helmets adorned with plastic stallions and straight up horse heads. Hats off to this crowd.

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A coordinated pair in pink and blue.
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More is more on Derby day.
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Quiet pastels work too.
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It’s never a bad idea to match your hat with your cocktail.
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The winner by a nose.
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A dashing suit for Derby day.
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The view from the top.
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Riders up!
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Derby bling means feathers, sequins and a unicorn.
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Proving you can still look fantastic during a Derby nap.
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The hats may get all the attention, but the dresses also deserve their due.
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A cowboy and his bow-tie.
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A magenta moment that is both practical and festive.
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This duo had us at yellow with their coordinating sunny standout looks.
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Can you spot the floral accent in this red, white and blue ensemble?
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A coordinated pair.
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Yay or neigh? This fan was happy to horse around when it came to his head gear. Credit...David Kasnic for The New York Times
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And they’re off! The Kentucky Derby is often described as “the most exciting two minutes in sports.”
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Pastels for the paddock (and flat shoes for a long day).
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The mad hatter?
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A dapper look for a day at the Derby.
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Wide-brimmed straw hats continue to be a winner for many racegoers — and the bigger the better.Credit...David Kasnic for The New York Times
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You can never go wrong with the classic straw hat.
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Thinking pink.
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One fan in full bloom.
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Ahoy sailor!Credit...David Kasnic for The New York Times
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It wouldn’t be the Derby without the mint juleps.Credit...David Kasnic for The New York Times
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Pearls, posies and lots of layered netting here for a millinery delight.Credit...David Kasnic for The New York Times
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An eye-popping race day outfit missing its owner.

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