The Kentucky Derby, America's longest-running sporting event, has been a cultural icon for over 152 years. It combines horse racing with a celebration of fashion and celebrity at Churchill Downs Racetrack.
Key points
Kentucky Derby is America's longest-running sporting event
Event combines horse racing with fashion and celebrity
Held at Churchill Downs Racetrack for over 152 years
Known as the 'Run for the Roses'
Mentioned in this story
Churchill Downs Racetrack
Kentucky Derby
A pillar of American tradition for more than a century and a half, the Kentucky Derby has long been more than a horse race. The famed “Run for the Roses,” the nation’s longest‑running continuously held sporting event, unfolds like a living tapestry of history and spectacle.
Beneath the twin spires of Churchill Downs Racetrack, thundering hooves share the spotlight with a dazzling parade of high profile celebrities and fashion — including sweeping wide‑brimmed hats, sculptural fascinators, and whimsical headpieces that bloom across the grandstands like a garden in full bloom.
For 152 years, style, sport and celebrities have woven together at the iconic racetrack, each vying for the spotlight in a celebration as richly American as the Derby itself.
The history of the Kentucky Derby
Understanding the Kentucky Derby’s place in American history is best understood by the stories of the horses, trainers, owners and others who’ve experienced the event.
“It’s up there with the Super Bowl and the World Series and the Masters and Wimbledon,” Louisville native and Daily Racing Form reporter Marty McGee previously told The Courier Journal. “If you ask any horseman the one race they want to win, it’s the Kentucky Derby. Why is that? It’s certainly the greatest race in the world.”
Kentucky Derby 152 contender Chief Wallabee during a morning workout at Churchill Downs. The horses enters the Kentucky Derby off a third-place finish in the Grade 1 Florida Derby on March 28 at Gulfstream Park. He currently ranks 17th on the Kentucky Derby points leaderboard with 50. April 19, 2026
2026 Kentucky Derby contender Albus on the backside at Churchill Downs in Louisville, Kentucky. The horse is trained by Riley Mott. April 20, 2026
Q&A
What is the history of the Kentucky Derby?
The Kentucky Derby has a rich history spanning over 152 years, showcasing stories of horses, trainers, and owners who have shaped the event.
Why is the Kentucky Derby called the 'Run for the Roses'?
The Kentucky Derby is nicknamed the 'Run for the Roses' because the winning horse is awarded a blanket of roses, symbolizing victory.
What makes the Kentucky Derby a significant American tradition?
The Kentucky Derby is significant as it combines horse racing with a celebration of American culture, fashion, and celebrity, making it a unique event in sports history.
Where is the Kentucky Derby held?
The Kentucky Derby is held at Churchill Downs Racetrack in Louisville, Kentucky.
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Japanese horse Wonder Dean, a contender for the 2026 Kentucky Derby, on the track with Churchill Downs veteran rider Mike Crowder aboard his pony at Churchill Downs in Louisville, Kentucky. April 20, 2026
Jockey Junior Alvarado walks by a sign honoring Sovereignty -- which he rode to a win in the 2025 Kentucky Derby -- at trainer Bill Mott's barn at Churchill Downs in Louisville, Kentucky. He's slated to ride Kentucky Derby horse Chief Wallabee. April 20, 2026
Kentucky Derby 152 contender Chief Wallabe outside trainer Bill Mott's barn at Churchill Downs. The horses enters the Kentucky Derby off a third-place finish in the Grade 1 Florida Derby on March 28 at Gulfstream Park. He currently ranks 17th on the Kentucky Derby points leaderboard with 50. April 19, 2026.
2026 Kentucky Derby contender Wonder Dean works at Churchill Downs in Louisville, Kentucky. Trainer is Daisuke Takayanagi. The horse has earned $725,172 so far. April 20, 2026
Jockey Junior Alvarado aboard 2026 Kentucky Derby horse Chief Wallabee during morning workouts at Churchill Downs in Louisville, Kentucky. The horse is trained by Bill Mott. The horse's most recent race was in the Florida Derby at Gulfstream Park, where he finished third. April 20, 2026
Jockey Junior Alvarado aboard 2026 Kentucky Derby horse Chief Wallabee during morning workouts at Churchill Downs in Louisville, Kentucky. The horse is trained by Bill Mott. The horse's most recent race was in the Florida Derby at Gulfstream Park, where he finished third. April 20, 2026
2026 Kentucky Derby contender Chief Wallabee is walked back his stall at trainer Bill Mott's barn on the backside of Churchill Downs in Louisville, Kentucky. April 19, 2026
2026 Kentucky Derby contender Wonder Dean works at Churchill Downs in Louisville, Kentucky. Trainer is Daisuke Takayanagi. The horse has earned $725,172 so far. April 20, 2026
2026 Kentucky Derby contender Incredibolt in his stall at Trainer Riley Mott's barn at Churchill Downs in Louisville, Kentucky. The Pin Oak Stud won the Virginia Derby. April 20, 2026
Kentucky Derby 152 contender Albus on the track with exercise rider Antonio Garcia aboard for training at Churchill Downs in Louisville, Kentucky. The horse is trained by Riley Mott. April 20, 2026
Kentucky Derby 152 contender Albus on the track with exercise rider Antonio Garcia aboard for training at Churchill Downs in Louisville, Kentucky. The horse is trained by Riley Mott. April 20, 2026
Two-time Kentucky Derby winning trainer Bill Mott at his barn on the backside at Churchill Downs in Louisville, Kentucky. Mott has Chief Wallabee in the 152nd Kentucky Derby. April 20, 2026
Trainer Riley Mott in the stall of 152nd Kentucky Derby contender Albus while working at his barn on the backside at Churchill Downs in Louisville, Kentucky. Riley, who has two horses in the 2026 Kentucky Derby -- Albus and Incredibolt -- is the son of Derby winning trainer Bill Mott. April 20, 2026
Trainer Riley Mott carries the saddlecloth of 152nd Kentucky Derby contender Albus while working in his barn on the backside at Churchill Downs in Louisville, Kentucky. Riley, who has two horses in the 2026 Kentucky Derby -- Albus and Incredibolt -- is the son of Derby winning trainer Bill Mott. April 20, 2026
2026 Kentucky Derby contender Albus on the backside at Churchill Downs in Louisville, Kentucky. The horse is trained by Riley Mott. April 20, 2026
Trainer Riley Mott on the backside during morning workouts at Churchill Downs in Louisville, Kentucky. Riley, who has two horses in the 2026 Kentucky Derby -- Albus and Incredibolt -- is the son of Derby winning trainer Bill Mott. April 20, 2026
Trainer Riley Mott watches training on the backside at Churchill Downs in Louisville, Kentucky. Riley, who has two horses in the 2026 Kentucky Derby -- Albus and Incredibolt -- is the son of Derby winning trainer Bill Mott. April 20, 2026
Japanese horse Wonder Dean, a contender for the 2026 Kentucky Derby, on the track with Churchill Downs veteran rider Mike Crowder aboard his pony at Churchill Downs in Louisville, Kentucky. April 20, 2026
Jockey Junior Alvarado on the backside at Churchill Downs in Louisville, Kentucky. He's slated to ride Kentucky Derby horse Chief Wallabee for trainer Bill Mott. Alvarado won the 2025 Kentucky Derby aboard Sovereignty. April 20, 2026
Jockey Junior Alvarado at trainer Bill Mott's barn at Churchill Downs in Louisville, Kentucky. He's slated to ride Kentucky Derby horse Chief Wallabee. April 20, 2026
Jockey Junior Alvarado aboard 2026 Kentucky Derby horse Chief Wallabee during morning workouts at Churchill Downs in Louisville, Kentucky. The horse is trained by Bill Mott. April 20, 2026
Japanese horse Wonder Dean, a contender for the 2026 Kentucky Derby, on the track with Churchill Downs veteran rider Mike Crowder aboard his pony at Churchill Downs in Louisville, Kentucky. April 20, 2026
2026 Kentucky Derby horse Right To Party on the track during a morning workout at Churchill Downs in Louisville, Kentucky. April 20, 2026
2026 Kentucky Derby horse Right To Party on the track during a morning workout at Churchill Downs in Louisville, Kentucky. April 20, 2026
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A peek at the backside of Churchill Downs during Kentucky Derby Week
Kentucky Derby 152 contender Chief Wallabee during a morning workout at Churchill Downs. The horses enters the Kentucky Derby off a third-place finish in the Grade 1 Florida Derby on March 28 at Gulfstream Park. He currently ranks 17th on the Kentucky Derby points leaderboard with 50. April 19, 2026
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A peek at the backside of Churchill Downs during Kentucky Derby Week
Kentucky Derby 152 contender Chief Wallabee during a morning workout at Churchill Downs. The horses enters the Kentucky Derby off a third-place finish in the Grade 1 Florida Derby on March 28 at Gulfstream Park. He currently ranks 17th on the Kentucky Derby points leaderboard with 50. April 19, 2026
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A peek at the backside of Churchill Downs during Kentucky Derby Week
2026 Kentucky Derby contender Albus on the backside at Churchill Downs in Louisville, Kentucky. The horse is trained by Riley Mott. April 20, 2026
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A peek at the backside of Churchill Downs during Kentucky Derby Week
Japanese horse Wonder Dean, a contender for the 2026 Kentucky Derby, on the track with Churchill Downs veteran rider Mike Crowder aboard his pony at Churchill Downs in Louisville, Kentucky. April 20, 2026
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A peek at the backside of Churchill Downs during Kentucky Derby Week
Jockey Junior Alvarado walks by a sign honoring Sovereignty -- which he rode to a win in the 2025 Kentucky Derby -- at trainer Bill Mott's barn at Churchill Downs in Louisville, Kentucky. He's slated to ride Kentucky Derby horse Chief Wallabee. April 20, 2026
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A peek at the backside of Churchill Downs during Kentucky Derby Week
Kentucky Derby 152 contender Chief Wallabe outside trainer Bill Mott's barn at Churchill Downs. The horses enters the Kentucky Derby off a third-place finish in the Grade 1 Florida Derby on March 28 at Gulfstream Park. He currently ranks 17th on the Kentucky Derby points leaderboard with 50. April 19, 2026.
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See full field of horses racing in the 2026 Kentucky Derby
2026 Kentucky Derby contender Wonder Dean works at Churchill Downs in Louisville, Kentucky. Trainer is Daisuke Takayanagi. The horse has earned $725,172 so far. April 20, 2026
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A peek at the backside of Churchill Downs during Kentucky Derby Week
Jockey Junior Alvarado aboard 2026 Kentucky Derby horse Chief Wallabee during morning workouts at Churchill Downs in Louisville, Kentucky. The horse is trained by Bill Mott. The horse's most recent race was in the Florida Derby at Gulfstream Park, where he finished third. April 20, 2026
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A peek at the backside of Churchill Downs during Kentucky Derby Week
Jockey Junior Alvarado aboard 2026 Kentucky Derby horse Chief Wallabee during morning workouts at Churchill Downs in Louisville, Kentucky. The horse is trained by Bill Mott. The horse's most recent race was in the Florida Derby at Gulfstream Park, where he finished third. April 20, 2026
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A peek at the backside of Churchill Downs during Kentucky Derby Week
2026 Kentucky Derby contender Chief Wallabee is walked back his stall at trainer Bill Mott's barn on the backside of Churchill Downs in Louisville, Kentucky. April 19, 2026
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A peek at the backside of Churchill Downs during Kentucky Derby Week
2026 Kentucky Derby contender Wonder Dean works at Churchill Downs in Louisville, Kentucky. Trainer is Daisuke Takayanagi. The horse has earned $725,172 so far. April 20, 2026
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A peek at the backside of Churchill Downs during Kentucky Derby Week
2026 Kentucky Derby contender Incredibolt in his stall at Trainer Riley Mott's barn at Churchill Downs in Louisville, Kentucky. The Pin Oak Stud won the Virginia Derby. April 20, 2026
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A peek at the backside of Churchill Downs during Kentucky Derby Week
Kentucky Derby 152 contender Albus on the track with exercise rider Antonio Garcia aboard for training at Churchill Downs in Louisville, Kentucky. The horse is trained by Riley Mott. April 20, 2026
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A peek at the backside of Churchill Downs during Kentucky Derby Week
Kentucky Derby 152 contender Albus on the track with exercise rider Antonio Garcia aboard for training at Churchill Downs in Louisville, Kentucky. The horse is trained by Riley Mott. April 20, 2026
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A peek at the backside of Churchill Downs during Kentucky Derby Week
Two-time Kentucky Derby winning trainer Bill Mott at his barn on the backside at Churchill Downs in Louisville, Kentucky. Mott has Chief Wallabee in the 152nd Kentucky Derby. April 20, 2026
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A peek at the backside of Churchill Downs during Kentucky Derby Week
Trainer Riley Mott in the stall of 152nd Kentucky Derby contender Albus while working at his barn on the backside at Churchill Downs in Louisville, Kentucky. Riley, who has two horses in the 2026 Kentucky Derby -- Albus and Incredibolt -- is the son of Derby winning trainer Bill Mott. April 20, 2026
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A peek at the backside of Churchill Downs during Kentucky Derby Week
Trainer Riley Mott carries the saddlecloth of 152nd Kentucky Derby contender Albus while working in his barn on the backside at Churchill Downs in Louisville, Kentucky. Riley, who has two horses in the 2026 Kentucky Derby -- Albus and Incredibolt -- is the son of Derby winning trainer Bill Mott. April 20, 2026
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A peek at the backside of Churchill Downs during Kentucky Derby Week
2026 Kentucky Derby contender Albus on the backside at Churchill Downs in Louisville, Kentucky. The horse is trained by Riley Mott. April 20, 2026
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A peek at the backside of Churchill Downs during Kentucky Derby Week
Trainer Riley Mott on the backside during morning workouts at Churchill Downs in Louisville, Kentucky. Riley, who has two horses in the 2026 Kentucky Derby -- Albus and Incredibolt -- is the son of Derby winning trainer Bill Mott. April 20, 2026
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A peek at the backside of Churchill Downs during Kentucky Derby Week
Trainer Riley Mott watches training on the backside at Churchill Downs in Louisville, Kentucky. Riley, who has two horses in the 2026 Kentucky Derby -- Albus and Incredibolt -- is the son of Derby winning trainer Bill Mott. April 20, 2026
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A peek at the backside of Churchill Downs during Kentucky Derby Week
Japanese horse Wonder Dean, a contender for the 2026 Kentucky Derby, on the track with Churchill Downs veteran rider Mike Crowder aboard his pony at Churchill Downs in Louisville, Kentucky. April 20, 2026
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A peek at the backside of Churchill Downs during Kentucky Derby Week
Jockey Junior Alvarado on the backside at Churchill Downs in Louisville, Kentucky. He's slated to ride Kentucky Derby horse Chief Wallabee for trainer Bill Mott. Alvarado won the 2025 Kentucky Derby aboard Sovereignty. April 20, 2026
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A peek at the backside of Churchill Downs during Kentucky Derby Week
Jockey Junior Alvarado at trainer Bill Mott's barn at Churchill Downs in Louisville, Kentucky. He's slated to ride Kentucky Derby horse Chief Wallabee. April 20, 2026
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A peek at the backside of Churchill Downs during Kentucky Derby Week
Jockey Junior Alvarado aboard 2026 Kentucky Derby horse Chief Wallabee during morning workouts at Churchill Downs in Louisville, Kentucky. The horse is trained by Bill Mott. April 20, 2026
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A peek at the backside of Churchill Downs during Kentucky Derby Week
Japanese horse Wonder Dean, a contender for the 2026 Kentucky Derby, on the track with Churchill Downs veteran rider Mike Crowder aboard his pony at Churchill Downs in Louisville, Kentucky. April 20, 2026
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See full field of horses racing in the 2026 Kentucky Derby
2026 Kentucky Derby horse Right To Party on the track during a morning workout at Churchill Downs in Louisville, Kentucky. April 20, 2026
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A peek at the backside of Churchill Downs during Kentucky Derby Week
2026 Kentucky Derby horse Right To Party on the track during a morning workout at Churchill Downs in Louisville, Kentucky. April 20, 2026
Matt Winn, former vice president and general manager of Churchill Downs, is credited with popularizing the Kentucky Derby in the early 20th century. In 1915, Winn convinced Harry Payne Whitney to ship his highly regarded filly, Regret, from New Jersey to compete in the Kentucky Derby. Regret became the first filly to win the race, giving the Kentucky Derby national recognition.
“I do not care if she never wins another race, nor if she never starts in another race,” Whitney told the Daily Racing Form at the time. “She has won the greatest race in America, and I am satisfied."
Regret’s victory came four years before Sir Barton became the first Triple Crown winner in 1919, long before the Triple Crown became an official designation in the 1930s. Sir Barton won the Kentucky Derby on May 10, the Preakness on May 14 and the Belmont on June 11. He actually won another race — the Withers Stakes — on May 24 between the Preakness and Belmont.
But more than five decades since his 1973 triumph, Secretariat remains the most popular winner of the Kentucky Derby and Triple Crown.
He graced the cover of Time Magazine, has several statues in his honor and was the subject of a Disney movie. His winning time of 1:59 2/5 remains a Derby record.
While the horses are the stars, the Kentucky Derby has turned several trainers, owners and jockeys into household names.
Ben Jones is one of two trainers to win the Kentucky Derby six times. His first victory came with Lawrin in 1938, and his final one came with Hill Gail in 1952.
D. Wayne Lukas, who died in 2025, became the face of horse racing in the 1980s. He won the Derby four times from 1988-99 and in 1996 became the first trainer ever to enter five horses in a Kentucky Derby, winning with Grindstone.
In 2020 with Authentic, Bob Baffert tied Ben Jones with his sixth Kentucky Derby victory. Baffert appeared to get his record-breaking seventh win with Medina Spirit in 2021, but the horse ultimately was disqualified for a drug violation. Baffert was reinstated for racing at Churchill Downs in 2025.
No owner has enjoyed more success than Calumet Farm, the Lexington institution that won the Kentucky Derby eight times from 1941 with Whirlaway to 1968 with Forward Pass under the leadership of Warren and Lucille Wright. Calumet was known for its devil red and blue racing silks and employed Ben Jones as its trainer.
Whirlaway in action on May 2, 1941. All the tremendous power and muscular coordination are shown as he worked out at Churchill Downs for his record-breaking run a few days later in the Derby. Here's Whirlaway in action. All the tremendous power and muscular coordination is shown as he worked out at Churchill Downs for his record-breaking run a few days later in the 1941 Kentucky Derby. May 2 1941.
Whirlaway in action on May 2, 1941. All the tremendous power and muscular coordination are shown as he worked out at Churchill Downs for his record-breaking run a few days later in the Derby. Here's Whirlaway in action. All the tremendous power and muscular coordination is shown as he worked out at Churchill Downs for his record-breaking run a few days later in the 1941 Kentucky Derby. May 2 1941.
African-American jockeys dominated the race in the early years, including Oliver Lewis aboard Aristides in the inaugural 1875 event. Isaac Murphy won the Derby three times from 1884-91, and Jimmy Winkfield won back-to-back Derbys with His Eminence (1901) and Alan-a-Dale (1902). Winkfield was the last African-American jockey to win the race.
To date, jockeys Eddie Arcaro and Bill Hartack share the Kentucky Derby record with five victories apiece.
The role of fashion at the Kentucky Derby
Since 1875, Kentucky Derby‑goers have known one truth: The right outfit can feel as triumphant as a winning ticket. There may be no strict rules for Derby style, but bold fashion has always been part of the thrill.
Each year, women flow through the gates at Louisville's historic racetrack wearing flirty sundresses, sophisticated spectator suits and bold, bright prints. Not to be outdone, gentlemen sport seersucker suits, bow ties, floral shirts and light straw fedoras, bowlers or Pork Pie hats.
Fashion models burst from the starting gate at Churchill Downs, wearing the latest styles for the upcoming Kentucky Derby. 1965
Style was a sure bet for the Kentucky Derby Saturday at Churchill Downs in Louisville, Ky. May, 6, 2023.
High fashion at the Kentucky Derby. May 4, 1963
A woman showed off her dress while at the Kentucky Derby. By Robert Steinau, The Courier-Journal. May 4, 1968
A couple sport matching outfits while attending the Kentucky Derby. By Robert Steinau, The Courier-Journal. May 4, 1968.
A woman sported diamond shaped sun glasses while attending the Kentucky Derby. May 4, 1968
Fashion at the Kentucky Derby. Bl May 2, 1970
Fashion at the Kentucky Derby. 1991
Fashion at the Kentucky Derby. 1979
A woman wore an elaborate hat to the Kentucky Derby. May 5, 1973
Jane Menko, of Santa Ana, CA., and her mother Gladys Knaster, of Louisville dressed in horse themed Derby attire while attending the race. May 5, 1973
Peter Outlaw of Philadelphia attending the Kentucky Derby in style. May 5, 1973.
Fashion at the Kentucky Derby. 1972
Fashion at the Kentucky Derby. 1972
Men's fashion at the Kentucky Derby. May 6, 1972
A man dresses in broad plaid pants to attend the Kentucky Derby. May 2, 1970
A woman shows off her fashionable clothing while attending the Kentucky Derby. May 2, 1970,
A woman wore an elaborate horse shoe hat to the Derby. May 2, 1970
Fashion at the Kentucky Derby. May 2, 1970
A couple sport matching outfits while attending the Kentucky Derby. May 4, 1968.
A woman showed off her dress while at the Kentucky Derby. May 4, 1968
Even the fashion conscious were prepared for the rain and cold weather at the Derby. . May 6, 1967
Mrs.Francis Ebenkamp and her hat at the Kentucky Derby. May 4, 1963
Mr. John Parker wore his cowboy hat to the Kentucky Derby. May 4, 1963
Mrs. Dean Lowe and her hat at the Kentucky Derby. . May 4, 1963
Mrs. Delbert Johnson and her hat at the Kentucky Derby. May 4, 1963
Fashion at the Kentucky Derby. . May 4, 1963
Fashion at the Kentucky Derby. . May 4, 1963
Fashion at the Kentucky Derby. May 4, 1963
Fashion at the Kentucky Derby. May 4, 1963
Fashion at the Kentucky Derby. May 4, 1963
Two women enjoyed mint juleps at the Kentucky Derby. May 6, 1961
Fashion at the 1961 Kentucky Derby. May 6, 1961
A woman with a fruit basket Derby hat sat in the paddock area at Churchill Downs on Derby day. May 6, 1961
A couple looked over the racing program at Churchill Downs on Derby day. May 6, 1961
Fashion at the Kentucky Derby. May 6, 1961
A lady shows off her clock faced hat at the Derby. May 6, 1961
Mrs. Dan Brosnan of Albany Ga. and Ms. William Fawcett of Atlanta Ga. suffered through a rainy Kentucky Derby. The poncho Ms. Fawcett is wearing was designed especially for the Kentucky Derby by her. She is a professional model. May 7, 1955.
Kentucky Derby fashions. May 6, 1961.
Kentucky Derby fashions. May 6, 1961.
Kentucky Derby fashions. May 6, 1961.
Bessie Erlanger of Louisville sported a chemise and sack dress to the Kentucky Derby. May 3, 1958
Movie star Susan Hayworth at the Kentucky Derby. . May 4, 1957
The Duke Edward and Duchess Wallis Simpson, of Windsor are the center of the media's attention at the Kentucky Derby. May 5, 1951
Mrs. George P. Robbins, Jr. of New Orleans enjoyed a drink and a bet at the Derby. May 5, 1951
Movie star Ann Sheridan attended the Kentucky Derby. May 5, 1951
Mrs. Marc Wymond and her Kentucky Derby guests. . April 27, 1948
Miss Naomi Layne of Columbus, Oh, Glen Ohsner and Mary Weaver enjoyed the infield of the Kentucky Derby. May 1, 1948
A scene from Kentucky Derby day at Churchill Downs. May 3, 1941
Clara Winn, left and Mrs. Turner Summers enjoyed their day at Churchill Downs. April 26, 1941
Mr. and Mrs Wathen Kneblekamp enjoyed their day at Churchill Downs. April 26, 1941
Fashion at the 1991 Kentucky Derby.
No other information with photo.
Vintage Derby Fashion
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SEE IT: A look back at 150 years of Kentucky Derby fashion
Fashion models burst from the starting gate at Churchill Downs, wearing the latest styles for the upcoming Kentucky Derby. 1965
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SEE IT: A look back at 150 years of Kentucky Derby fashion
Fashion models burst from the starting gate at Churchill Downs, wearing the latest styles for the upcoming Kentucky Derby. 1965
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SEE IT: A look back at 150 years of Kentucky Derby fashion
Style was a sure bet for the Kentucky Derby Saturday at Churchill Downs in Louisville, Ky. May, 6, 2023.
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SEE IT: A look back at 150 years of Kentucky Derby fashion
High fashion at the Kentucky Derby. May 4, 1963
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SEE IT: A look back at 150 years of Kentucky Derby fashion
A woman showed off her dress while at the Kentucky Derby. By Robert Steinau, The Courier-Journal. May 4, 1968
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SEE IT: A look back at 150 years of Kentucky Derby fashion
A couple sport matching outfits while attending the Kentucky Derby. By Robert Steinau, The Courier-Journal. May 4, 1968.
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SEE IT: A look back at 150 years of Kentucky Derby fashion
A woman sported diamond shaped sun glasses while attending the Kentucky Derby. May 4, 1968
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SEE IT: A look back at 150 years of Kentucky Derby fashion
Fashion at the Kentucky Derby. Bl May 2, 1970
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SEE IT: A look back at 150 years of Kentucky Derby fashion
Fashion at the Kentucky Derby. 1991
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SEE IT: A look back at 150 years of Kentucky Derby fashion
Fashion at the Kentucky Derby. 1979
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SEE IT: A look back at 150 years of Kentucky Derby fashion
A woman wore an elaborate hat to the Kentucky Derby. May 5, 1973
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SEE IT: A look back at 150 years of Kentucky Derby fashion
Jane Menko, of Santa Ana, CA., and her mother Gladys Knaster, of Louisville dressed in horse themed Derby attire while attending the race. May 5, 1973
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SEE IT: A look back at 150 years of Kentucky Derby fashion
Peter Outlaw of Philadelphia attending the Kentucky Derby in style. May 5, 1973.
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SEE IT: A look back at 150 years of Kentucky Derby fashion
Fashion at the Kentucky Derby. 1972
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SEE IT: A look back at 150 years of Kentucky Derby fashion
Fashion at the Kentucky Derby. 1972
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SEE IT: A look back at 150 years of Kentucky Derby fashion
Men's fashion at the Kentucky Derby. May 6, 1972
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SEE IT: A look back at 150 years of Kentucky Derby fashion
A man dresses in broad plaid pants to attend the Kentucky Derby. May 2, 1970
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SEE IT: A look back at 150 years of Kentucky Derby fashion
A woman shows off her fashionable clothing while attending the Kentucky Derby. May 2, 1970,
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SEE IT: A look back at 150 years of Kentucky Derby fashion
A woman wore an elaborate horse shoe hat to the Derby. May 2, 1970
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SEE IT: A look back at 150 years of Kentucky Derby fashion
Fashion at the Kentucky Derby. May 2, 1970
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SEE IT: A look back at 150 years of Kentucky Derby fashion
A couple sport matching outfits while attending the Kentucky Derby. May 4, 1968.
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SEE IT: A look back at 150 years of Kentucky Derby fashion
A woman showed off her dress while at the Kentucky Derby. May 4, 1968
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SEE IT: A look back at 150 years of Kentucky Derby fashion
Even the fashion conscious were prepared for the rain and cold weather at the Derby. . May 6, 1967
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SEE IT: A look back at 150 years of Kentucky Derby fashion
Mrs.Francis Ebenkamp and her hat at the Kentucky Derby. May 4, 1963
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SEE IT: A look back at 150 years of Kentucky Derby fashion
Mr. John Parker wore his cowboy hat to the Kentucky Derby. May 4, 1963
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SEE IT: A look back at 150 years of Kentucky Derby fashion
Mrs. Dean Lowe and her hat at the Kentucky Derby. . May 4, 1963
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SEE IT: A look back at 150 years of Kentucky Derby fashion
Mrs. Delbert Johnson and her hat at the Kentucky Derby. May 4, 1963
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SEE IT: A look back at 150 years of Kentucky Derby fashion
Fashion at the Kentucky Derby. . May 4, 1963
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SEE IT: A look back at 150 years of Kentucky Derby fashion
Fashion at the Kentucky Derby. . May 4, 1963
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SEE IT: A look back at 150 years of Kentucky Derby fashion
Fashion at the Kentucky Derby. May 4, 1963
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SEE IT: A look back at 150 years of Kentucky Derby fashion
Fashion at the Kentucky Derby. May 4, 1963
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SEE IT: A look back at 150 years of Kentucky Derby fashion
Fashion at the Kentucky Derby. May 4, 1963
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SEE IT: A look back at 150 years of Kentucky Derby fashion
Two women enjoyed mint juleps at the Kentucky Derby. May 6, 1961
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SEE IT: A look back at 150 years of Kentucky Derby fashion
Fashion at the 1961 Kentucky Derby. May 6, 1961
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SEE IT: A look back at 150 years of Kentucky Derby fashion
A woman with a fruit basket Derby hat sat in the paddock area at Churchill Downs on Derby day. May 6, 1961
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SEE IT: A look back at 150 years of Kentucky Derby fashion
A couple looked over the racing program at Churchill Downs on Derby day. May 6, 1961
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SEE IT: A look back at 150 years of Kentucky Derby fashion
Fashion at the Kentucky Derby. May 6, 1961
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SEE IT: A look back at 150 years of Kentucky Derby fashion
A lady shows off her clock faced hat at the Derby. May 6, 1961
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SEE IT: A look back at 150 years of Kentucky Derby fashion
Mrs. Dan Brosnan of Albany Ga. and Ms. William Fawcett of Atlanta Ga. suffered through a rainy Kentucky Derby. The poncho Ms. Fawcett is wearing was designed especially for the Kentucky Derby by her. She is a professional model. May 7, 1955.
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SEE IT: A look back at 150 years of Kentucky Derby fashion
Kentucky Derby fashions. May 6, 1961.
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SEE IT: A look back at 150 years of Kentucky Derby fashion
Kentucky Derby fashions. May 6, 1961.
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SEE IT: A look back at 150 years of Kentucky Derby fashion
Kentucky Derby fashions. May 6, 1961.
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SEE IT: A look back at 150 years of Kentucky Derby fashion
Bessie Erlanger of Louisville sported a chemise and sack dress to the Kentucky Derby. May 3, 1958
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SEE IT: A look back at 150 years of Kentucky Derby fashion
Movie star Susan Hayworth at the Kentucky Derby. . May 4, 1957
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SEE IT: A look back at 150 years of Kentucky Derby fashion
The Duke Edward and Duchess Wallis Simpson, of Windsor are the center of the media's attention at the Kentucky Derby. May 5, 1951
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SEE IT: A look back at 150 years of Kentucky Derby fashion
Mrs. George P. Robbins, Jr. of New Orleans enjoyed a drink and a bet at the Derby. May 5, 1951
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SEE IT: A look back at 150 years of Kentucky Derby fashion
Movie star Ann Sheridan attended the Kentucky Derby. May 5, 1951
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SEE IT: A look back at 150 years of Kentucky Derby fashion
Mrs. Marc Wymond and her Kentucky Derby guests. . April 27, 1948
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Miss Naomi Layne of Columbus, Oh, Glen Ohsner and Mary Weaver enjoyed the infield of the Kentucky Derby. May 1, 1948
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A scene from Kentucky Derby day at Churchill Downs. May 3, 1941
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Clara Winn, left and Mrs. Turner Summers enjoyed their day at Churchill Downs. April 26, 1941
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Mr. and Mrs Wathen Kneblekamp enjoyed their day at Churchill Downs. April 26, 1941
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Fashion at the 1991 Kentucky Derby.
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Vintage Derby Fashion
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"We wear what makes us feel amazing," Kentucky-based fashion consultant Jo Ross previously told The Courier Journal.
Whether seated in the upscale Millionaires Row or roaming the less-pricey infield, fans take the phrase "go big or go home" quite literally, especially when it comes to their hats.
Since the first Kentucky Derby in 1875, well-heeled spectators have arrived at Churchill Downs sporting coordinating hats, dresses, bags and shoes, all thanks to Col. Meriwether Clark Jr., the founder of Churchill Downs, who had a vision of modeling the races after British horse racing. Part of his plan to change the image of American racetracks from places of ill-repute to venues of high society included encouraging fans to dress to the nines. With the help of his wife, Clark campaigned to create a posh event. His plan worked. Right out of the starting gate, elegantly dressed ladies and gentlemen arrived for a day at the races.
By the 1920s, The Courier Journal was splashing photos of race‑day fashion across its pages, spotlighting stylish fans — especially women — and dissecting their outfits in lavish detail. It didn’t take long for spectators to realize that a showstopping Derby look was the surest ticket to turning heads at Churchill Downs and landing in the next morning’s paper. When CBS broadcast the Kentucky Derby nationwide for the first time in 1952, the rest of America finally got to witness the spectacle for themselves, cementing the race as a runway as much as a sporting event.
America's hat-wearing habits began to shift in the 1960s, marking a turning point in Kentucky Derby hat history. While the hat was an everyday accessory for much of the first half of the century, by the 1960s, people were no longer wearing them as part of everyday attire. Wearing a hat to the Kentucky Derby, however, became the exception.
“Televised coverage of the massive crowds at the Kentucky Derby meant that if you wanted to stand out and get noticed, your hat needed to be big and bold," said Jessica Whitehead, senior curator of collections at the Kentucky Derby Museum. “Some are large and elegant; others are homemade novelty creations that you’ll only find on Derby Day at Churchill Downs.”
While “head-to-toe” fashion has changed dramatically during the Kentucky Derby’s 152-year history, the finishing touch of wearing a fancy or unique hat is a vital thread woven into the culture of the historic event.
“Derby fashion keeps evolving, and dazzling, year after year,” said Christine A. Moore, a Featured Milliner of the Kentucky Derby. “Elevated fashion on Derby Day, it’s here to stay."
Aside from a dramatic headpiece, the mint julep is the other must-have trackside accessory. If you find yourself holding a winning ticket in one hand, there is nothing better to occupy your opposite hand than the traditional drink of the Kentucky Derby. Churchill Downs annually serves up around 120,000 mint juleps on race day.
Celebrities at the Kentucky Derby through the decades
Spectacle has always drawn the world’s elite, and the Kentucky Derby is no exception. Hollywood and sport heavyweights like Jack Nicholson, Steven Spielberg, Michael Jordan, Tom Brady, Travis Kelce and even Kurt Vonnegut have made the pilgrimage to Churchill Downs on the first Saturday in May.
The father of Gonzo journalism and Louisville native, Hunter S. Thompson, wrote his seminal sports article, "The Kentucky Derby Is Decadent and Depraved" after attending the race in 1970.
Dubbed “the sport of kings,” America’s most iconic horse race has also lured presidents and royalty. King Rainier of Monaco and his son, Prince Albert, took in the action, the Duke and Duchess of Windsor arrived in 1951, and Prince Aly Khan followed in 1958. The most celebrated royal visit came in 2007, when Queen Elizabeth II and Prince Philip graced the grandstand, cementing the Derby’s status as a global stage for power, prestige and pageantry.
Churchill Down's president at the time, the late Steve Sexton, told The Sydney Morning Herald the Queen of England was "certainly the most prestigious guest" in the modern-day history of the Kentucky Derby.
The tight security at the 133rd Kentucky Derby which Queen Elizabeth attended is a far cry from how notable dignitaries and celebrities experienced the Kentucky Derby in the 1940s through 1980s.
Photographs of President Nixon and his wife, Pat, show the leader of the free world mingling with the crowd as the couple ambled through the public grandstands in 1969. In total, nine U.S. presidents have attended the Derby, though only Nixon did so while in office.
Early Courier Journal images of comedian Bob Hope also show him seated in a spectator box where anyone with a ticket could easily drop by and say hello.
Today, celebrities including sports figures, Grammy Award-winning musicians, titans of industry, Pulitzer Prize-winning authors and stars of television and film are whisked through an entrance at Churchill Downs and escorted to a red carpet where members of the media ask them about their picks for that year's Kentucky Derby, their fashion choice, whether they enjoy the mint julep cocktail and if they attended a celebrity gala the previous evening.
The most famous of the Derby Eve galas has been hosted since 1989 by Patricia Barnstable-Brown. The former actress and model hosts a legendary charity gala at her private home in Louisville's Highlands neighborhood with her family. Over the years, the Barnstable Brown Gala has drawn numerous repeat guests, from Joey Fatone of NSYNC fame and Super Bowl Champion Tom Brady to country music legends such as Tanya Tucker.
"We love that our guests ask to come back year after year. No one wants to throw a party that people don't want to come back to," Barnstable-Brown previously told The Courier Journal. "The fact that our party is now in its 37th year and our guests won't miss it is the highest compliment."
The gala annually raises millions of dollars for diabetes research, and Condé Nast named it to its top 10 parties in the world list.
In its earliest years, long before television or social media, the Kentucky Derby was a local event attended by the high society of Louisville. Newspaper accounts detailed the “celebrity” horsemen and women and local politicians who attended the first Kentucky Derby on a sunny spring day in 1875. Two years later, Churchill Downs hosted its first international celebrity, when the Polish actress Helena Modjeska attended the races.
"Early on celebrities were primarily politicians, horsemen and women, and the social elite," Whitehead said. "It wasn't until Hollywood started cranking out movies and creating 'stars' that celebrities as we know them today started showing up on the first Saturday in May."
Among the most recognizable early celebrities at Churchill Downs were Susan Hayward, Louisville native Muhammad Ali, novelist John Steinbeck, Lee Majors, Dennis Hopper, Marlo Thomas, Andy Williams and former President Gerald Ford.
No matter the era, the star power and standout style scattered across the stands infuse the tradition of American horse racing at Churchill Downs with a charge all its own, turning the first Saturday in May into a dazzling mix of glamour, energy and pure Kentucky Derby magic.
