Hats were always worn to the Kentucky Derby, but they haven't always been the wildly large, dramatic affairs seen at Churchill Downs on the first Saturday of May. See how the cloches, boaters and fedoras of yesteryear morphed into the sun hats and fascinators of today.
26 photos
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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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Getty Images
Derby attendees watch War Admiral win the Kentucky Derby, May 8, 1937.
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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.
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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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John Dominis/Time Life Pictures/Getty Images
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.
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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.
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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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Robert Riger/Getty Images
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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Kit Houghton/Corbis via Getty Images
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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Timothy A. Clary/AFP via Getty Images
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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Jon Levy/AFP via Getty Images
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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Gail Kamenish/AP
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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Jeff Haynes/AFP via Getty Images
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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Jeff Snyder/FilmMagic
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.
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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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Rob Carr/Getty Images
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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Matthew Stockman/Getty Images
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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Stephen J. Cohen/Getty Images
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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Shaban Athuman/Getty Images
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.
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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.
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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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Ian Johnson/Icon Sportswire via Getty Images
Fancy hats on display at the 145th running of the Kentucky Derby at Churchill Downs on May 4th, 2019, in Louisville, Kentucky.
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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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Michael Reaves/Getty Images
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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Getty Images
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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Zach Bolinger/Icon Sportswire via Getty Images
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.
