How Eye-Catching Hats Became a Kentucky Derby Fashion Trademark
What began as an elite custom morphed into a grand show of symbolic reverence, as the Derby played host to some of the most diverse displays of head wear worldwide
By Danielle Abreu ••
It’s the most prestigious prize in horse racing – and the most elusive
The Kentucky Derby may be the greatest two minutes in sports, but at Churchill Downs on Saturday, the competition parading in the stands could give the thoroughbreds a run for their money.
From towering hat designs festooned with ribbons to delicate fascinators, the modern taste for the Derby's trademark accessory has spawned contests at parties, and given business a boost for milliners.
Although the annual battle for the Derby's most eye-catching hat has taken on a life of its own in recent decades, the tradition of wearing one to the race traces back to day one, says Kentucky Derby Museum curator Chris Goodlett.
When Meriweather Lewis Clark Jr., the grandson of legendary explorer William Clark of the Lewis and Clark expedition, founded the Kentucky Derby, he wanted to bring elegance and class to American horse racing, inspired by the grand races of London and Paris.
Defying social norms that excluded women from places men were gambling, he marketed his race to the fashionable upper crust. That meant women appeared front and center at the races, dressed in stylish clothes, shoes and — the centerpiece of the wardrobe — a dashing hat.
"The presence of ladies in the grandstand added great splendor to the racing scene," Goodlett said. "News articles in 1875 make reference to the dress of the ladies, with specific mention of hats."
Eventually, in the 1960s, women began wearing larger and more extravagant hats, the better to be seen in the stands on television. What began as an elite custom morphed into a grand show of symbolic reverence, as the Derby played host to some of the most diverse displays of head wear worldwide.
Mrs. Woodrow Wilson, widow of the late President Wilson shown as she attended the running of the Kentucky Derby wearing a simple straw cloche hat at Louisville, Kentucky, May 6, 1933.
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Derby attendees watch War Admiral win the Kentucky Derby, May 8, 1937.
he Abbott Sengstacke Family Papers/Robert Abbott Sengstacke/Getty Images
Spectators watch in the grandstand during the Kentucky Derby’s Diamond Jubilee, Louisville, Kentucky, May 1949. Hats become slightly more ornate during this time, though they would not reach the opulence of modern day Derby hats for a few more years.
John Dominis/Time Life Pictures/Getty Images
Not all attendees during the 50s wore demure hats – some, like the women seen above, were a harbinger of what the Derby could come to look like among attendees in terms of fashion.
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Spectators covering up in the rain at Churchill Downs on Kentucky Derby day, 1955. Hats for both women and men continued to be part of everyday public life, and the Derby was no exception.
From left: trainer R. L. Wheeler, owner Cornelius V. Whitney, jockey Willie Shoemaker and Mrs. Whitney pose for pictures as Kentucky Governor Bert Combs presents a julep cup to the owners of Tompion after the Kentucky Derby favorite captured Keenland’s featured Bluegrass Stakes.
Bill Shoemaker’s wife gives him a kiss at the 94th running of the race at Churchill Downs, in 1968. The rise in televised events in the 60s encouraged bigger, showier fascinators and hats, according to the Kentucky Derby museum.
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Three women in suits and matching hats cheer during the 1977 Kentucky Derby, Louisville, Kentucky, May 7, 1977. Attendees have started showing more personality in their headwear, though some still preferred to keep their hats simple.
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A woman wears a flamboyant hat decorated with a plastic horse’s head in this 1986 photo. Hats became elaborate works of art once the Derby became the place to see or be seen.
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Col. Charles Matasich and George Holter, wearing two of the most photographed hats at the Kentucky Derby, pose for pictures while waiting for the first race at Churchill Downs in Louisville, Kentucky. May 3, 1997. Women and men have traditionally worn their best, and their showiest, to the Kentucky Derby.
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Women young and old wear traditional derby hats in the paddock area at Churchill Down in Louisville, Kentucky, in this 1998 photo.
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Tracey Cherry, from Del Ray Beach, Florida, dons her derby hat during Kentucky Derby Day celebrations at Churchill Downs Saturday, May 6, 2000 in Louisville, Kentucky.
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Eric Williams of Chicago, IL, looks over his racing form at Churchill Downs in Louisville, Kentucky the site of the 129th running of the Kentucky Derby. May 3, 2003. Hats have gradually changed from an indicator of genteel dress into an outlet of self expression and artistry by the turn of the century.
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A contestant for the Kentucky Derby Hat Contest at Churchill Downs as seen in 2004 in Louisville, Kentucky, United States. Hats have gradually changed from an indicator of genteel dress into an outlet of self expression and artistry by the turn of the century.
Jason Kempin/WireImage
Kim Kardashian seen at the 135th Kentucky Derby at Churchill Downs on May 2, 2009, in Louisville, Kentucky. Derby hat brims have gradually grown wider and looser at the turn of the century, compared to stiffer brims worn by attendees the decades prior.
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Ky Col. Charles M. Matasich looks on during the 137th Kentucky Derby at Churchill Downs on May 7, 2011, in Louisville, Kentucky.
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A fan looks on from the stands while she wears her derby hat during the 137th Kentucky Derby at Churchill Downs on May 7, 2011, in Louisville, Kentucky. Derby hats have only gotten wider and more elaborate with each passing year.
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A view of a Derby hat at the 140th Kentucky Derby at Churchill Downs on May 3, 2014, in Louisville, Kentucky. Social media and derby hat contests have only spurred the creation and appreciation of creative millinery during the Derby.
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A woman wearing a festive hat looks on prior to the 143rd running of the Kentucky Derby at Churchill Downs on May 6, 2017, in Louisville, Kentucky.
Michael Loccisano/Getty Images for Churchill Downs
Victoria Justice attends the Kentucky Derby on May 5, 2018 in Louisville, Kentucky. The Derby has become the place to stretch traditional concepts of headwear, departing from the pillboxes and cochises of old.
Michael Loccisano/Getty Images for Churchill Downs
Figure skater Johnny Weir seen at the Kentucky Derby 144 on May 5, 2018, in Louisville, Kentucky. Men are no stranger to ornate headwear at the Derby, as Weir proves.
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Fancy hats on display at the 145th running of the Kentucky Derby at Churchill Downs on May 4th, 2019, in Louisville, Kentucky.
Robin Marchant/Getty Images for Churchill Downs
Outsized hats made of sinamay, netting or crinoline featuring large amounts of feathers, like the one seen on a guest here on May 4, 2019, is now a Derby staple.
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A woman wearing a frilled fascinator looks on prior to the 145th running of the Kentucky Derby at Churchill Downs on May 4, 2019, in Louisville, Kentucky.
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An attendee wears a derby hat and face mask during the 146th Kentucky Derby on Sept. 5, 2020, at Churchill Downs in Louisville. Ornate masks-and-hat pairings became standard in response to hosting the Derby during the coronavirus.
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An attendee wears a derby hat and face mask during the 146th Kentucky Derby on Sept. 5, 2020, at Churchill Downs in Louisville. Ornate masks-and-hat pairings became standard in response to hosting the Derby during the coronavirus.
Today, the annual Run for the Roses can be the backbone of many milliners', or women's hatmakers, shops every year, with business booming in the April run-up to the big event.
"When I first opened the boutique, I made one or two hats for the Derby," said milliner Linda Pagan, who owns The Hat Shop in New York and has been creating one-of-a-kind Derby hats for close to 20 years. "Now, it is the biggest month of our year."
The process of custom-making a hat is labor-intensive, and a Derby hat can take weeks to create. Many of Pagan’s clients start shopping for the perfect Derby hat as early as January, especially those who plan on wearing a grandiose wide-brim headpiece.
Celebrating the Derby in style doesn't have to mean an enormous hat, though. There's also the fascinator, a sort of cross between a miniature hat and a hair accessory, embellished with feathers, flowers, beads or lace and perched on the side of a woman's head, in a style that Kate, the Duchess of Cambridge, has made unmistakable.
How to make the official drink of the Kentucky Derby, the Mint Julep.
Philip Treacy, the famed Irish milliner who designed 36 hats for the royal wedding (including the infamous "Teletubby" one) and almost single-handedly revived the fascinator, has pronounced the style dead, to his delight, but it still has its fans at races stateside. The Louisville Courier-Journal's fashion editor Christine Fellingham estimates that a third of Derby-goers now wear fascinators.
They're stylish, sure, but Pagan points out that they're also easy to wear, and transport.
"Once upon a time, airlines use to have special sections on-board for storing hat boxes," Pagan notes. Now, due to ever-tougher luggage restrictions, "wild horse" shoppers who wait until the last stretch to score a hat may have to settle for a humble cocktail hat or fascinator.
That modern-day practical consideration could keep fascinators a popular choice for the Derby's hat-donning ladies, just as wide-brimmed hats once were for Derby-goers hoping not to burn their fair skin in the blazing sun of the grandstands.
These one-of-kind pieces can be expensive, too.
Some racegoers are willing to spend up to $1,000 or more to land the perfect accessory to their outfit. However, if you're lucky enough to get tickets to the annual "Big Brims and Fancy Trims" sample hat sale at the Kentucky Derby Museum in Louisville, attendees can find head pieces for as low at $19, with no hat priced over $75.
Whatever hat a Derby fan chooses — whether it's off the rack or custom-made, awe-inspiringly elegant or gruesomely garish — Pagan says there's a key to finding the perfect one: "Confidence."
