Kentucky Derby Hats: Revisting the Best Derby Hats Through the Years

The Kentucky Derby is technically centered around horses, but it's also all about the hats. Kentucky Derby attendees have been wearing fancy hats to the annual race every event since 1875's inaugural race when Colonel Meriwether Clark Jr. decided to model the race after British horseracing. That idea meant men and women had to follow strict dress codes, including the inclusion of decadent hats.

Why Hats and Fancy Dress?

Clark founded Churchill Downs, where the derby is held, and his wife, Mary, encouraged women to dress in their finest outfits for the event, Yahoo! Sports shares. Hats were also a frequent accessory worn by Southern women when they got dressed up, specifically for church and other formal events. As hats became less popular in people's everyday wardrobes, they retained their prominence at the Kentucky Derby, and the event became one of only a few occasions where they were worn, making them a favorite part of the annual race.

What Are Derby Hats Called?

A Kentucky Derby hat is sometimes confused with a bowler hat, which is not the correct term. Instead, a wide-brimmed sunhat is your typical Kentucky Derby hat, typically adorned with a bow.

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(Photo: Getty / John Dominis)
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(Photo: Getty / Robert Riger)

What Role Did Television Play?

The Kentucky Derby was first televised in 1952, prompting derby hats to become larger and more extravagant in an attempt to stand out from the crowd. Styles now include wide-brimmed hats, fascinators, headbands, parasols, ascots, fedoras and more. Some attendees choose to go with a sleek and simple look while others go all-out, decorating their headpieces with fruit, flowers, miniature horses and more.

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(Photo: Getty / Kit Houghton / Dylan Buell / Jamie Squire)
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(Photo: Getty / Andy Lyons)

Changes to the Kentucky Derby 2021

During the 147th Kentucky Derby on May 1, attendees will be required to wear masks, as Kentucky currently has an executive order in place that requires the use of face coverings in most public settings. This shouldn't be an issue for most derby day ensembles, as milliners have been adding face masks to their collections since 2020. Some are choosing to accompany their hats with equally eye-catching or color-matching masks, while others are keeping their face coverings neutral.

Can Women Wear Pants at the Kentucky Derby?

Women can wear pants, but denim should be avoided at all costs. Dress pants or dress clothing should be worn. Business casual is the line to follow. But for many, the glamour and prestige of the event brings out wild interpretations of more traditional looks.

"It’s all about the hat, we want the attention to be on the women’s headwear and on their dresses," said designer Rachel Bell. "The mask should really blend with the outfit, because the focus is on the hat." Bell and Kate Smith own The Hat Girls and are the official hat designers of the Kentucky Derby Festival for the sixth year in a row. They created 720 hats for this year's race and are offering 32 different shades of colors they can pull from dresses or hats to create a perfectly matching face mask.

While wide-brimmed hats will certainly be spotted at Churchill Downs on Saturday, Bell estimates that smaller fascinators will be plentiful due to the fact that they're easy to wear with a mask. "We found it easier to convince people to go with a fascinator because it’s not covering your face as a big hat would do," she said. "With a wide brim all you are going to see is the eyes, if you have the mask and sunglasses on."

What's The Difference Between a Hat and Fascinator?

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A hat is a larger, wide-brimmed typically made for a bolder statement. While a fascinator is a lacy scarf according to Southern Living that women have "fastened" around their heads. For 2021, fascinators will be in high demand due to mask requirements.

She also guessed that attendees at the 2021 derby will dress even fancier than usual after a year of wearing sweatpants on the couch. "I think people will tend to dress up a little more this year," she mused. "Since we have been at home wearing athleisure for the last year or so, we expect to see really nice outfits out on the tracks."