The Best And Worst-Dressed Celebs At The 2025 Kentucky Derby

While the Kentucky Derby is technically a sports race event that has been held annually in Churchill Downs in Louisville, Kentucky, for the past 150 years, it has also become a social event where fashion plays a major role. And each year, a number of celebs attend the race to show off their interpretation of Kentucky Derby style.

When asked what she predicts will be trending at this year's event, the Kentucky Derby's official style editor, Zanna Roberts Rassi, told Country Living, "The pastel theme! I know that's not groundbreaking, but not pastel like easter egg colors, much cooler shades of pastel like pistachio greens, butter yellow, baby blues, blush pinks. Go for cooler pastels." For "no-brainer instant Derby style," Roberts Rassi recommends a traditional hat. Now, while we have seen a few pastels and lots of hats, not every celebrity nailed the event's fashion rules — but luckily, a few did the Kentucky Derby justice with their choices, proving the event is still one of the most fun fashion outings of the year.

If this were for another occasion, Alix Earle's outfit would definitely be on the best dress list; however, when it comes to the Kentucky Derby, we certainly expect fun colors to ring in the summer. The social media personality's dress and hat combo, on the other hand, was more suited for a funeral — and we mean this in the nicest way possible. Of course, she still looked gorgeous (Alix Earle even looks stunning makeup-free), so we can forgive her for this fashion faux pas.

Influencer and former gymnast Olivia "Livvy" Dunne was definitely one of the few who saved the event's fashion this year. Dunne showed up in a white minidress with black polka dots and a perfectly matching white hat. The look was simple yet youthful and fun, thanks to the shortness of the dress and the mesh material that covered the top portion of it. The star definitely showed everyone how to find the perfect balance between eye-catching and classic.

We have to admit that we expected way more from reality star Melinda Berry. When she showed up to the event in a ruffled pink maxi dress with a whimsical pattern, our initial thought was that the look was great — until we saw her hat and her shoes. Now, don't get us wrong: We love a one-toned look, but we fear that Berry needs to read up on our ultimate guide to putting together a perfect monochromatic outfit. While we could have looked past the color of the hat, it was the Barbie-esque shade of her pink heels that threw the entire look completely off.

Even though some may have put Gai Waterhouse's funky look on the worst-dressed side of this list, at Glam, we can definitely appreciate a daring and authentic fashion moment, especially if it doesn't follow the usual fashion rules. The Australian horse trainer and businesswoman showed up to this year's Kentucky Derby in a fun pantsuit, sneakers, and a simple hat. The look was quirky and unusual, but Waterhouse pulled it off — and with fashion that is half the game!

Cookbook author and "Top Chef" judge Gail Simmons had a good thing going, but her hat ruined it. There is a fine line between pulling off a maximalist look and looking ridiculous, and we fear that Simmons needs to work on this trend a tad more. We adore the dress she chose for the occasion, but the hat was just working against it instead of with it.

Gymnast Simone Biles was undoubtably one of the best dressed of the event. The Olympic athlete showed up at the 2025 Kentucky Derby in an ultra-short, strapless, hot-pink minidress and a matching hat. The look suited the star perfectly as it was youthful, confident, and bold — all things that Biles herself exudes, too. In fact, we adore Simone Biles' complete transformation from a young gymnast to one of the most well-known (and fashionable) female athletes in the world.

We get it — styling a wide-brimmed hat without looking like Freddy Krueger isn't always easy, but we certainly expect the ladies at the Kentucky Derby to nail it. Unfortunately, journalist and television personality Star Jones hasn't quite mastered the art of it yet. Jones showed up at the annual event in a simple white dress with feather details, but the colorful hat definitely seemed like a last-minute decision as it didn't match any part of her outfit.

Olympic athlete Molly Carlson definitely helped Zanna Roberts Rassi's prediction come true as she showed up at the event in a muted, pastel, sky-blue gown. The vintage cut of the dress, combined with the fact that the color perfectly accentuated Carlson's copper hair, certainly earned her a spot on the best-dressed part of this list.

While Molly Carlson's pastel color choice accentuated her features, Selma Blair's ended up washing her out. The '90s and early-aughts Hollywood icon definitely has enough red carpets under her belt to know that wearing the wrong color can instantly take a look from fab to drab. Had this dress been in a fun jewel tone to help enhance her hair color and features, she definitely would have found herself on the other side of the list. But hey, there's always next year!