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, Bill Belichick and Jordon Hudson, Dylan Dreyer, former *NSYNC members Lance Bass and Joey Fatone, singer Luis Fonsi, Dee Dee Sorvino and Lolo Jones, amongst others.
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. Here are the best and worst dressed stars from the event.
BEST DRESSED
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
Bill Belichick and Jordon Hudson matched in black ensembles at the race. Hudson donned a dark dress that had a ruffled skirt, a sheer one-shouldered neck piece and a dramatic studded belt. Her head piece was on the simpler side and paired nicely with her gown. As for Belichick, he wore a classic black suit
Actress Danica McKellar looked very colorful at the event. The Wonder Years star donned a floral haltered gown, which she paired with a pink and orange hat and it was just the right amount of color if you ask us
Today show’s Dylan Dreyer opted for a white floral mini dress and some nude heels. For her choice of headpiece, she donned a big blue hat that had various colored flowers and ruffles on top of it
*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 with 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 patterned white gown at the event, but it was her bold blue and white hat that really stole the show
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 and their looks looked great together
Nicole Scherzinger looked classy in her polka dot white dress, which contained a tight bodice, flowing skirt and bows on the waistline. She accessorized with a big black hat that contained a ruffle on the top and they worked nicely together
Too Hot to Handle star Melinda Berry was pretty in pink at the 2026 Kentucky Derby. She donned a lacy crop top and matching skirt, which she paired with some tan heels and a blue and pink headpiece that contained a veil over her face
The Real Housewives of Atlanta’s Angela Redd Oakley attended the event in a figure-hugging black and white polka dot dress, which she paired with black pumps and a pink and black feathered headpiece. Her husband, Charles Oakley, kept it simple in a tan sports jacket over a while polo shirt and matching trousers
Anna Nicole Smith’s look-alike daughter Dannielynn Birkhead made a rare appearance as she attended the Kentucky Derby on Saturday in chic Mac Duggal strapless black gown, whuch had an enormous white flower on it, platformed heels and a black and white feathered headpiece. Dannielynn, 19, was spotted at the prestigious horse race with her dad, Larry Birkhead
Actress Gina Torres opted for a button-down shirt dress which she paired with some leather boots, a dramatic black belt, a tan sun hat and a patterned purse. The tone-downed but fashionable ensemble accentuated her enviable physique perfectly
Brazilian model Lais Ribeiro and her husband, basketball star Joakim Noah, both looked great at the Kentucky Derby. Ribeiro wore a chic black pantsuit, a brown scarf and a green feathered headpiece. As for Noah, he chose a leather jacket, black trousers, sneakers and a brown bucket hat
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
Model and TV personality Camille Kostek showcased 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
WORST DRESSED
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 turquoise ensemble that contained shorts, high socks and a tan bowtie. As for Patrick Harris, he wore maroon pants and a colorful suit jacket
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
Chaka Khan’s over-the-top ensemble was a total fashion fail. She donned a sheer top and awkward puffy skirt, tights, knee-high leather boots, a huge Dolce and Gabbana belt and black hat
Dasha’s outfit totally clashed thanks to the two different patterns. She donned a lace-up black crop top and a floral, rauched skirt as well as some black pumps
Riche Sambora was spotted in a bright orange jacket, black shirt and bellbottom pants. He accessorized with a few silver necklaces and a fedora 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
