The Best (and Biggest) Hats at the 2019 Kentucky Derby

Most fans head to Louisville’s Churchill Downs on the first Saturday in May to watch the Kentucky Derby. Others attend the annual Run for the Roses to be seen. After all, the most exciting two minutes in sports leaves a lot of extra time for the show ponies who love parading around Millionaires Row or the famous infield.

For the145th running of the race, celebrities and die-hard thoroughbred fans once again took great pride in showing off their Derby Day finery, which typically means big, colorful hats. (Never mind that the spectator behind you might actually want to see the race itself.)

Because roses are the official flowers of the Derby—the winner is draped in a red blanket of them—hats decorated with bouquets (and other petal patterns) are often in full bloom each year.

But the whole garden is well represented as fans opt for floral hats and other fragrant millinery.

Those who don’t care for flowers at the Derby typically keep it light with feathered hats.

And classic Derby Day tropes such as mint juleps, Churchill Downs’ iconic twin spires and of course horses themselves are also among the homemade headwear patterns seen around the track.

For spectators who don’t opt for a wide-brimmed sun hat—particularly on a day that called for rain—a fascinator is a more modest, but no less chic, Derby favorite.

Naturally, the men at Churchill Downs can’t resist some Derby Day frippery—but like any hat, they’re typically over the top.

And celebrities love getting into the act with Derby Day hats and fashion finery. Before the race, Jimmy Fallon and Steve Higgins showed off some millinery options on the Tonight Show.

While on the red carpet, celebrities showed off their millinery magic.

And then there are those Derby fans who just prefer to let their heads shine.


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