Kentucky Derby 2026 best and worst dressed stars: Enormous hats, bizarre feathered headpieces and over-the-top floral frocks take over the prestigious horse race

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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. 

And as expected, the star-studded guests have certainly not disappointed with their dramatic ensembles.

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 show up in colorful outfits and decadent dresses – as well as their most head-turning hats.

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.’ 

And while many of the dramatic head pieces and bright outfits totally worked, others were just a little too much, resulting in some major fashion fails.

From enormous hats to feathered frocks, the Daily Mail has rounded up all the dramatic looks from the 2026 Kentucky Derby.

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

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

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

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

*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

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

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

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

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

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

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

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. One of the more dramatic hats worn by an attendee at this year's Kentucky Debry is seen
Another of the more dramatic hats worn by an attendee at this year's Kentucky Debry is seen

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

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 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. Another over-the-top feathered hat that was spotted at the event is seen
One guest is pictured wearing an eye-popping purple, pink and blue feathered hat

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




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