Life Style

The Best (And Biggest) Hats At The 2021 Kentucky Derby

With considerably fewer spectators expected for this year’s Kentucky Derby weekend, there is one unintended benefit: Those massive, wide-brimmed hats and towering feathered fascinators probably won’t block many fans’ view of the track. Churchill Downs can accommodate 165,000 but less than 50,000 are expected due to Covid restrictions, which means there’s more room for the show ponies to show off their fine (and often homemade) headwear.

Dressing up for the Derby is a tradition as old as the race itself. When Colonel Merriwether Lewis Clark Jr.—grandson of the famed explorer—helped establish the race in 1875, he was inspired by England’s Epsom Derby, which had strict dress codes for spectators, including hats.

As fancy headwear was already a Southern tradition, Louisvillians immediately embraced the new fashion standard and by the time the Kentucky Derby was first televised in 1952, fine millinery was as prized as a fresh mint julep at Churchill Downs.

The frippery has now expanded to include vibrant ascots, patterned bow ties, lots of statement jewelry, and 2021’s must-have accessory—a face mask.

As roses are the official flowers of the Derby—the winner is draped in a red blanket of them—hats decorated with a giant bud, full bouquets and other floral patterns are usually in full bloom among spectators. (Red for Derby Day and pink for Friday’s Kentucky Oaks.)

Those who don’t opt for flowers at the Derby often bring a lighter touch to their toppers with feathered hats.

And classic Derby Day symbols such as mint juleps, Churchill Downs’ famed twin spires and the horses themselves are also among the homemade headwear seen around the stands.

While wide-brimmed sun hats are always popular along the homestretch—even on rainy days—a fascinator is chic, but more modest, Derby option.

Men are always game to step up their headwear game on Derby weekend— with flowers and other frivolity.

And then there were fans at Churchill Downs this year who couldn’t help reminding others that in the middle of a pandemic, some shots don’t have to be long to be winners.


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