The 2026 Kentucky Derby is almost upon us, and the festivities have already kicked off at Churchill Downs in Louisville, Kentucky, ahead of the coveted horse race. As expected, the star-studded guests have certainly not disappointed with their dramatic ensembles.
A Fashion Spectacle Like No Other
The annual competition, which will take place at 6:57 pm EST on Saturday, May 2, is not only a prestigious horse race but also a fashion spectacle with a very unique and special dress code. Each year, it has become tradition for attendees to show up in colorful outfits and decadent dresses, as well as their most head-turning hats.
Star Sightings at Churchill Downs
A slew of stars have been spotted at this year's event already, including Melissa Joan Hart, Neil Patrick Harris, former *NSYNC members Lance Bass and Joey Fatone, singer Luis Fonsi, Miss America Cassie Donegan, and actress Odette Annable. The racegoers showcased some truly eye-popping accessories and ensembles as they geared up to watch what has been dubbed 'the most exciting two minutes in sports.'
While many of the dramatic headpieces and bright outfits totally worked, others were just a little too much, resulting in some major fashion fails. From enormous hats to feathered frocks, here is a roundup of all the dramatic looks from the 2026 Kentucky Derby.
Melissa Joan Hart
Melissa Joan Hart arrived at the event wearing a blue, figure-hugging gown which contained a sultry cut-out in her midriff. She paired it with a bold white hat that had an enormous flower on top.
Neil Patrick Harris and David Burtka
David Burtka and Neil Patrick Harris had a little too much going on with their looks. Burtka donned a patterned turquoise ensemble that contained shorts, high socks, and a tan bowtie. Patrick Harris wore maroon pants and a colorful suit jacket.
Joey Fatone and Izabel Araujo
*NSYNC member Joey Fatone arrived in style, opting for a very bright turquoise suit and completing the look with colorful sneakers and a white fedora. His longtime girlfriend Izabel Araujo stunned in a similar-colored sheer floral dress, paired with strappy nude heels and a dramatic white hat embellished with an array of flowers.
Luis Fonsi and Águeda López
Singer Luis Fonsi looked dapper in a black and white plaid sports jacket, a button-down white shirt, white trousers, tan dress shoes, and a white and black hat. His wife, Águeda López, opted for a simple black gown, white Chanel pumps, a bold black hat with one white flower, and sheer gloves. The pair kept it simple but classy.
Cassie Donegan
Miss America Cassie Donegan stunned in a bright, floral mini dress with a tight bodice and A-line waist, leaving her long legs on full display. She completed the look with a black and red flower hat and black heels. Her ensemble had just the right amount of color without going overboard.
Odette Annable
Actress Odette Annable kept it very simple in a yellow satin dress and nude heels. Instead of a bold hat, she went with an understated feather headpiece. She attended with her Hallmark's Kentucky Derby co-star Andrew Walker, who wore a gray suit over a sky blue button-down shirt, loafers, and a big fedora.
Lance Bass and Michael Turchin
Lance Bass, seen with his husband Michael Turchin, wore an off-white matching jacket and pants over a yellow sweater. Turchin was seen in a blue sweater and jacket with white trousers.
Fashion Fails and Over-the-Top Hats
While many dramatic headpieces and bright ensembles worked, others missed the mark. One guest wore a bold red, white, and blue outfit with a cat's face etched onto the front, paired with cowboy boots, a big furry coat, a dramatic gold chain, and a leopard print cowboy hat. Another racegoer showcased a horse-shaped hat on his head. The event featured numerous over-the-top feathered hats, some of which were deemed fashion fails.
