Kentucky Derby fashion over the decades 1875-2024
Jan 19, 2024
Churchill Downs Grandstand 1895 (Photo courtesy of Kentucky Derby Museum)
The beauty of the Thoroughbred is not the only spectacle on display the first Saturday in May, when a field of 20 three-year-old horses race for a chance at glory in the Kentucky Derby (G1).
The eye-popping, extravagant fashion beneath the Twin Spires of Churchill Downs is a sight in itself, and each year Derby attendees from near and far put as much thought into what they’re wearing to the track as to which horse they’re betting in the most exciting two minutes in sports.
As we count down to the 150th running of the Kentucky Derby on May 4, let’s walk down memory lane and explore the evolution of Kentucky Derby fashion over the decades, from the inaugural race in 1875 all the way to the last edition of the Run for the Roses in 2023.
From the formal, floor-length dresses of the 1800s to the shorter hemlines of the early 1900s, the intricate detail of the roaring ‘20s to the more reserved styles of the ‘40s and ‘50s, fashion has transformed drastically, and at the same time has maintained particular conventions, over the course of the Derby’s 149-year history.
Today, you’ll find a mix of vintage and contemporary, bold and classic, and wild and demure when you arrive at the Derby, with people from all over the world looking to express their inner self while celebrating the Southern tradition of the Run for the Roses. And when it comes to the race’s most important accessory — the hat — there is no shortage of styles you will find adorned atop each racegoer’s head.
Shopping for something to wear before the first Saturday in May? Maybe one of these ensembles below will inspire the perfect getup for your latest venture to the Derby.
1875 — Kentucky Derby winner: Aristides
(Photo courtesy of Kentucky Derby Museum/Churchill Downs)
Aristides owner Henry McGrath (Photo courtesy of the Kentucky Derby Museum/Churchill Downs)
1877 — Kentucky Derby winner: Baden-Baden
Jockey William Walker (Photo courtesy of Kentucky Derby Museum/Churchill Downs)
1895 — Kentucky Derby winner: Halma
Churchill Downs Grandstand on Kentucky Derby day, 1895
(Photo courtesy of Kentucky Derby Museum/Churchill Downs)
1905 — Kentucky Derby winner: Agile
Samuel Culbertson, 5th president of Churchill Downs, prepares to attend the Kentucky Derby with guests. The horse drawn carriage sits outside his residence at 1432 S. 3rd Street in Louisville, Kentucky. (Photo courtesy of Kentucky Derby Museum/Churchill Downs)
1906 — Kentucky Derby winner: Sir Huon
(Photo courtesy of Kentucky Derby Museum/Churchill Downs)
1907 Sheepshead Bay crowd
(Photo courtesy of The Keeneland Library)
1908 — Kentucky Derby winner: Stone Street
(Photo courtesy of Kentucky Derby Museum/Churchill Downs)
1916 — Kentucky Derby winner: George Smith
(Photo courtesy of Kentucky Derby Museum/Churchill Downs)
1918 — Kentucky Derby winner: Exterminator
(Photo courtesy of Kentucky Derby Museum/Churchill Downs)
1919 — Kentucky Derby winner: Sir Barton
(Photo courtesy of Kentucky Derby Museum/Churchill Downs)
1924 — Kentucky Derby winner: Black Gold
(Photo courtesy of Kentucky Derby Museum/Churchill Downs)
1926 — Kentucky Derby winner: Bubbling Over
(Photo courtesy of Kentucky Derby Museum/Churchill Downs)
1929 – Photo of nurses. Kentucky Derby winner: Clyde Van Dusen
(Photo courtesy of Kentucky Derby Museum/Churchill Downs)
1936 — Kentucky Derby winner: Bold Venture
(Photo courtesy of Kentucky Derby Museum/Churchill Downs)
1939 — Kentucky Derby winner: Johnstown
(Photo courtesy of Kentucky Derby Museum/Churchill Downs)
1941 — Kentucky Derby winner: Whirlaway
(Photo courtesy of Kentucky Derby Museum/Churchill Downs)
1942 — Kentucky Derby winner: Shut Out
(Photo courtesy of Kentucky Derby Museum/Churchill Downs)
1949 — Kentucky Derby winner: Ponder
(Photo courtesy of Kentucky Derby Museum/Churchill Downs)
1958 Photo of jockey. Kentucky Derby winner: Tim Tam
(Photo courtesy of Kentucky Derby Museum/Churchill Downs)
1965 — Kentucky Derby winner: Lucky Debonair
(Photo courtesy of Kentucky Derby Museum/Churchill Downs)
1966 — Kentucky Derby winner: Kauai King
(Photo courtesy of Kentucky Derby Museum/Churchill Downs)
1968 — Kentucky Derby winner: Forward Pass
(Photo courtesy of Kentucky Derby Museum/Churchill Downs)
1969 — Photo of President Richard Nixon. Kentucky Derby winner: Majestic Prince
(Photo courtesy of Kentucky Derby Museum/Churchill Downs)
1970 — Kentucky Derby winner: Dust Commander
(Photo courtesy of Kentucky Derby Museum/Churchill Downs)
1971 — Kentucky Derby winner: Canonero II
(Photo courtesy of Kentucky Derby Museum/Churchill Downs)
1971 — Kentucky Derby winner: Canonero II
(Photo courtesy of Kentucky Derby Museum/Churchill Downs)
1974 — Kentucky Derby winner: Cannonade
(Photo courtesy of Kentucky Derby Museum/Churchill Downs)
1976 — Kentucky Derby winner: Bold Forbes
(Photo courtesy of Kentucky Derby Museum/Churchill Downs)
1977 — Kentucky Derby winner: Seattle Slew
(Photo courtesy of Kentucky Derby Museum/Churchill Downs)
1977 Photo of military on site. — Kentucky Derby winner: Seattle Slew
(Photo courtesy of Kentucky Derby Museum/Churchill Downs)
1977 — Kentucky Derby winner: Seattle Slew
(Photo courtesy of Kentucky Derby Museum/Churchill Downs)
1979 — Kentucky Derby winner: Spectacular Bid
(Photo courtesy of Kentucky Derby Museum/Churchill Downs)
1979 — Kentucky Derby winner: Spectacular Bid
(Photo courtesy of Kentucky Derby Museum/Churchill Downs)
1980 Photo of trainer. Kentucky Derby winner: Genuine Risk
(Photo courtesy of Kentucky Derby Museum/Churchill Downs)
1980 Photo of infield. Kentucky Derby winner: Genuine Risk
(Photo courtesy of Kentucky Derby Museum/Churchill Downs)
1981 — Kentucky Derby winner: Pleasant Colony
(Photo courtesy of Kentucky Derby Museum/Churchill Downs)
(Photo courtesy of Kentucky Derby Museum/Churchill Downs)
1990 Blue Grass Stakes
1990 Blue Grass Stakes. Finish of the race. Summer Squall, ridden by Pat Day outlasted Land Rush (Angel Cordero, Jr.) and Unbridled (Craig Perret) to win by 1 3/4 lengths on a muddy track. Summer Squall was owned by Dogwood Stable (W. Cothran Campbell) and trained by Neil J. Howard.
1998 — Photo of Jack Nicholson at the Kentucky Derby. Kentucky Derby winner: Winning Colors (filly)
(Photo courtesy of Kentucky Derby Museum/Churchill Downs)
1999 Keeneland crowd scene
1999 Terrace scene at Keeneland (Photo courtesy of Keeneland Association)
2019 — Kentucky Derby winner Country House
(Photo courtesy of Kentucky Derby Museum/Churchill Downs)
2019 — Kentucky Derby winner Country House
(Photo courtesy of Kentucky Derby Museum/Churchill Downs)
2022 — Kentucky Oaks
(Photo courtesy of Kentucky Derby Museum/Churchill Downs)
2023 — Kentucky Derby Winner Mage
Winnerc Circle. Mage with Javier Castellano riding wins the 2023 Kentucky Derby at Churchill Downs, KY (Photo by HorsePhotos)
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