Most horse racing fans head to Louisville’s Churchill Downs on the first Saturday in May watch the annual Run for the Roses. But plenty of show ponies are also there for the poses—showing off their Derby Day finery. And while those bold seersucker suits and vibrant floral sundresses may brighten up Millionaires Row and look great on TV, nothing tops a great topper at the Kentucky Derby. And no style is out of fashion. There are wide-brimmed “Southern belle” hats, fascinators, fedoras, porkpies, bowlers, boaters and, of course, some homemade headwear that might be better left at home.The tradition of dressing up for the first leg of the Triple Crown dates back to the earliest days of the Derby. In 1875, when Colonel Meriwether Lewis Clark Jr.—grandson of the famed American explorer—helped found the race, he took his inspiration from England’s Epsom Derby, which had formal dress codes for spectators, including hats. Clark believed that if those in attendance wore “full morning dress” it would help keep away the kinds of folks who might be drawn to a sporting event simply because there was gambling and drinking. (For more than 150 years, however, Derby fans have proven they can do all three at once.)Dressed From The Past: Some Derby Day spectators look appropriate for the first race—in 1875.Leandro Lozada / AFP via Getty ImagesSince fancy headwear was already a Southern tradition, Louisvillians embraced those high fashion standards. By the time the Derby was first televised in 1952, fine millinery was as prevalent as a fresh mint julep.Today, there is no official dress code at Churchill Downs, but spectators hardly need reminding that they are as much on parade as the Thoroughbreds in the paddock. Even fans who wouldn’t know a furlong from a farrier, understand that Derby Day requires the widest brims, the boldest colors and the most outrageous millinery.Flowers have long been a dominant theme with Derby dandies. Roses have been associated with the “most exciting two minutes in sports” since 1896, when the winning Thoroughbred, Ben Brush, was draped in a garland of pink and white roses. Big Red: Who needs a garland of roses when one big bloom makes a statement?Leandro Lozada / AFP via Getty ImagesEight years years later, red became the official color of the Derby rose and spectators have been in full bloom ever since. (Pink remains the official color of the Kentucky Oaks, a race for three-year-old fillies the Friday before the Derby.) The paddock and the infield are always filled with festive red, pink and white hats covered in bouquets of roses—or often one giant bloom.Blue Belle: Floral headwear is always a winner at the Kentucky DerbyAP Photo/Charlie RiedelOf course, other popular flowers can be found among the Derby’s Hat Pack. And given the number of julep-themed headwear seen around Churchill Downs every year, a mint sprig may technically count as part of a floral arrangement. For those who eschew the garden theme, bright plumage is a perennially popular choice for Churchill peacocks, while silk, tulle, and other diaphanous fabrics are always in fashion. The desire to go big on Derby Day can also mean that some fans sport something extra-wide or sky scraping, including hats that pay homage to Churchill’s iconic Twin Spires. Never mind that there may be someone sitting behind you who actually wants to watch the race.Go Big, Then Go Home: It's a tall order to see the race behind her at Churchill Downs.Jeff Schear/Getty Images for Churchill DownsEven those who opt for fascinators—headwear typically clipped to the hair or attached with a headband and worn on a jaunty angle—can cause heads to tilt behind them.Politicians Up!: New Mexico Governor Michelle Lujan Grisham arrived at Churchill Downs ready to ride.Daniel Boczarski/Getty Images for Churchill DownsOther spectators go right at the real reason for race day and festoon their homemade headwear with horses, horseshoes, jockey silks and other equine symbols. And celebrities—there every year to see and be seen—also love to throw their hats into the fashion fray. Several musicians—including Richie Sambora, Joey Fatone and Chaka Khan—hit a fashion high note. Two 1990s TV icons, Melissa Joan Hart and Danica McKellar arrived in floral finery. And plenty of past and present NFL stars—including New York Giants quarterback Jaxson Dart and Hall of Famer Warren Moon—traded in helmets for chic headwear. (Except for Rob Gronkowski, who just opted for a baseball cap.)It may not have been what Colonel Meriwether Lewis Clark Jr. had in mind, but he would surely tip his hat to the spectacle.Lucky Outfit: 'Mr. Derby' shows off his custom jacket made by his artist daughter, Twiggy Originals, and a hat adorned with his collection of Pegasus pins.Jeff Moreland/Icon Sportswire via Getty ImagesMORE FROM FORBESForbesMeet The Wily Billionaire Trucking Boss Behind Kentucky Derby Favorite RenegadeBy John HyattForbesA Simple Guide To Betting The Kentucky DerbyBy Danny BrewerForbes16 Bourbons To Use For The Best Mint Julep, According To BartendersBy Jillian DaraForbesThe Best Of Watches And Wonders 2026By Michael Solomon