Kentucky Derby 2026 greatest and worst dressed stars: Enormous hats and feathered frocks take over the horse race

The festivities ahead of the 2026 Kentucky Derby have officially kicked off at Churchill Downs in Louisville, Kentucky, and the star-studded guests have certainly not disappointed with their dramatic ensembles. 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

Joan Hart posed with fellow actress Danica McKellar, who looked very colorful at the event. The Wonder Years star donned a floral haltered gown which she paired with a pink and orange hat

David Burtka and Neil Patrick Harris had a little too much going on with their looks at the 2026 Kentucky Derby. Burtka donned a patterned turqouise ensemble that contained shorts, high socks and a tan bowtie. As for Patrick Harris, he wore maroon pants and a colorful suit jacket 

*NSYNC member Joey Fatone arrived at the event in style. He opted for a very-bright turquoise suit and completed the look with some colorful sneakers and a white fedora. His longtime girlfriend Izabel Araujo stunned in a similar-colored sheer floral dress which she paired with some strappy nude heels and a dramatic white had that was embellished with an array of flowers

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 on it and some sheer gloves. The pair kept it simple but classy

Dee Dee Sorvino and her husband John Schneider were seen in coordinated outfits at the event. Sorvino rocked a blue and white polka dot collared dress that contained an eye-popping broach in the center of the chest area. She completed the look wtih a matching hat, gloves and heeled boots. As for Schneider, he wore a white sports jacket over a light blue shirt and matching pants, as well as a necktie that had similar-colored polka dots to his wife’s dress

Lolo Jones ensured all eyes would be on her at the 2026 Kentucky Derby. She wore an intricate patterened white gown at the event, but it was her bold blue and white hat that really stole the show

Star Jones arrived at the event in a baby blue ruffled dress, colorful heels and an over-the-top feathered hat. She also put flowers in her hair and held on to a sparkly purse that matched her shoes. Her husband, Ricardo Lugo, kept it much more simple in an all-white look

Miss America Cassie Donegan stunned in a bright, floral mini dress that contained a tight bodice and A-line waist which left her long legs on full display. She completed the look with a black and red flower hat as well as some black heels. Her ensemble had just the right amount of color without going overboard, if you ask us

Actress Odette Annable kept it very simple in a yellow satin dress and some nude heels. Instead of a bold hat like others, she went with an understated feather headpiece. She attended the event with her Hallmark’s Kentucky Derby costar Andrew Walker, who wore a gray suit over a sky blue button-down shirt,  some loafers and a big fedora

Lance Bass, seen here with his husband Michael Turchin, wore an off-white matching jacket and pants over a yellow sweater to the race. Turchin, for his part, was seen in a blue sweater and jacket and some white trousers

Model and TV personality Camille Kostek accentuated her enviable physique in a black jacket with a low-cut polka dot neckline and a matching pencil skirt. She of course donned a big black hat, as well as some black and white heels and held a chic black Chanel purse

Model Tabitha Swatosh looked fashionable in her black and white shirt and skirt combo. The pale white ensemble contained black flowers. She paired the outfit with some white pumps and a big black hat

It has become tradition for attendees show up to the horse race in colorful outfits and decadent dresses – as well as their most head-turning hats, like the guests seen here

While many of the dramatic head pieces and bright ensembles totally worked, others were just a little too much, resulting in some major fashion fails. Some of the more dramatic hats worn by attendees at this year’s Kentucky Debry are seen

One guest was seen wearing a very bold red, white and blue outfit that had a cat’s face etched onto the front. He paired the ensemble with some cowboy boots, a big furry coat, a dramatic gold chain and a leopard print cowboy had 

The racegoers showcased some truly eye-popping accessories as they geared up to watch what has been dubbed ‘the most exciting two minutes in sports,’ like this man, who wore a horse-shaped hat on his head

The annual competition – which will take place at 6:57 pm EST on Saturday, May 2 – is not only a prestigious horse race, but a fashion spectacle with a very unique and special dress code. Some more of the over-the-top feathered hats spotted at the event are seen