The Worst-Dressed Celebs At The 2026 Kentucky Derby
Every year, a bunch of celebrities and regular people from all over gather to show off their strangest and most extravagant attire as they watch some horse races in the Kentucky sun. A surprising number of sports celebrities turned out for the 2026 Kentucky Derby, while other familiar faces from television, music, and more attended the star-studded gathering.
With such intense fashion looks at the Kentucky Derby, there are always going to be some that go too far, or don't go far enough, and 2026 was no different. There were plenty of outfits that really missed the mark, but who was the worst-dressed of the year?
From veteran sports stars to Grammy-winning singers, there were quite a few rough ensembles this year. Even the biggest celebrities have bad days when it comes to fashion. Here are a few of the worst-dressed stars at the Kentucky Derby that stood out for all the wrong reasons.
Chaka Khan looked dressed up for a stylish funeral
Edgy, Grammy-winning singer Chaka Khan tried her best to bring some experimental black-and-gold style to the 2026 Kentucky Derby. But unfortunately, it didn't work out as well as she planned.
Khan wore knee-high black boots with an asymmetrical skirt, a partially sheer shirt with three-quarter sleeves, and, of course, an extravagant black hat. But instead of high fashion, it looked more like Khan was dressed for a glam funeral or cosplaying a stylish witch, making this a major miss.
Rob Gronkowski missed the memo on the dress code
On the other end of the spectrum, retired football star Rob Gronkowski did too little for such a fashion-forward event. He showed up at the Kentucky Derby in khaki pants, a light blue button-up shirt, a dark blue jacket, and a matching baseball cap.
While Gronkowski isn't much of a style star, if you're going to the Kentucky Derby, you have to do something a little different with your outfit. Clearly, in this case, Gronkowski missed the memo, with his look much too simple for the event.
Sports star Avery Johnson and his wife had too much going on
Avery Johnson, former basketball player and coach and current sports analyst, attended the Kentucky Derby with his wife, Cassandra Johnson. If it were just Avery on his own, it's possible his outfit wouldn't have stood out so much, but thanks to Cassandra's look, the couple ended up on the worst-dressed list.
Cassandra showed up in a white long-sleeved dress that featured a high neck and a pattern of bright flowers. She paired the dress with tie-around heels with flowers on them, a matching purse, and a flower headband, while Johnson's light blue suit was paired with a bold striped tie. Too many colors and flowers overwhelmed the Johnsons' outfits.
Joey Fatone and his wife went overboard with the teal
Toeing the line between chicly eye-catching and too over-the-top is truly a difficult task at the Kentucky Derby. For NSYNC member Joey Fatone and his wife, Kelly Baldwin, they'll need to try again next time, because their 2026 get-ups did not work.
The couple went for all-teal looks, and while the color choice can certainly work at the Kentucky Derby, there was just too much of it here, especially in Fatone's case. The singer wore an all-teal suit with a white button-up shirt that appeared to have a painted graphic on it, along with a white fedora hat and teal, green, and yellow sneakers.
Star Jones' bright blue and floral look was all over the place
The look that former "The View" host Star Jones chose for the 2026 Kentucky Derby was so close to working out, but despite the over-the-top nature of the event, her outfit had a smidge too much stuff happening on it. Jones wore a light blue strapless minidress with pointed heels, a purse, and a huge hat in blues and purples. She also had some flowers in similar colors woven into her hair.
The color choice was perfect for Jones and felt very fitting for spring, but the ensemble was too all over the place. Jones should have done the hat or flowers in the hair, not both, and the patterns and colors on the shoes and purse did not match everything else.
Former Bon Jovi member Richie Sambora was too rocker for his own good
Some celebrities need to realize that classic is the best for a reason. At the Kentucky Derby, you want to stick as close to the theme as possible unless you're really confident in your own style; otherwise, it will turn out like former Bon Jovi member Richie Sambora's outfit.
The singer and musician arrived at the 2026 races in a black shirt with matching pants that looked a little too long on him. On top of that, he added a gold-accented layer, an orange velvet jacket, and a tilted tan fedora with a polka-dot sash. There's quite a bit to Sambora's outfit, and regrettably, even his rocker vibe couldn't save the ensemble.