The Worst-Dressed Celebs Of May 2025

May 2025 was a busy month for celebs and Hollywood elites. From the Met Gala to the AMAs, the ACMs, and the Cannes Film Festival, there were more than enough red carpets to go around. While some celebrities stunned us with gorgeous looks that sparked serious style envy, others showed up in outfits that felt more like horror stories designers tell each other around a campfire.

A recurring theme we noticed was designers attempting to cram multiple aesthetics into a single look without properly blending them. Fashion may be leaning more into expressionism — and we genuinely applaud creative risks — but at the end of the day, the point of fashion is to look good. When expression cancels out beauty, a celeb ends up on the worst-dressed list. This May, we saw bizarre silhouettes, clashing fabrics, and ill-fitted pieces that clearly didn't work, and somehow, these outfits still made it past the designers, stylists, and celebs themselves.

Only a handful of dresses manage to miss the mark in every possible area, and somehow, Jordan Chiles managed to find two of them and combine them into one outfit. The exposed lace-up chest is far too wide to be flattering, the zips on the hips ruin the only part of the dress that might've been passable, and what is that bottom skirt? A balloon? A deflated tutu? This dress is an absolute shame because white could've looked breathtakingly stunning on her if she had picked the right outfit. On the bright side, since Chiles was one of the worst-dressed celebrities at the 2025 American Music Awards, it's virtually impossible for her to show up at the AMAs next year in something worse. Silver lining ... we guess?

Heidi Klum may have missed the memo, but triangular silhouettes aren't exactly popular. For some reason, the usually stunning model paired a boxy upper half with linebacker shoulders and added a ruffled train that doesn't even look like part of the dress. We love a good knee-high boot, but in this case, it just feels like Heidi picked it simply because it was black. And that brings us to another major issue: The outfit is pure black. Everyone knows an all-black look can easily read as dated, and this one is no exception. But let's be honest, even a pop of color couldn't have saved this. The hair is a 10, but the outfit is a crime.

Crop suit jacket, tiny baby tie, draped sash across, flowery shoes, sheer thighs — it seems as though Aimee Lou Wood's stylist combined every idea they've ever had into one outfit. It's imbalanced and chaotic, and looks more like a design-school mood board than a finished look. The 2025 Met Gala's theme was "Superfine: Tailoring Black Style" with a "Tailored For You" dress code, and needless to say, this 'fit failed because there's no way it was properly tailored for the "Daddy Issues" actor.

From the lavender tone to the tentacle-like fringe and even the red lips, Julia Garner's outfit felt less red carpet-ready and more like a re-imagination of Ursula from "The Little Mermaid." Worse still, the limp fringes swallow her shape entirely, and the center slit only adds to the awkwardness. But more than anything else, this look is a push for folks to understand why skin undertones matter and how to figure theirs out. If Garner's stylist had considered the concept more, they might have chosen a color that didn't completely wash Garner out and make her almost invisible in the dress. 

It's a sad day when a fashion icon tops our list of the worst-dressed celebs at the 2025 Met Gala, but Vera Wang had this one coming. All artists know the urge to combine two concepts, but the key has always been in blending them to avoid harsh lines — or, in fashion speak, styling them so the pieces feel cohesive. Vera Wang's dress at the Met Gala completely missed that. The harsh transition between the drape and the giant feather explosion made it look like two separate looks were stitched together in a rush. The top is cut too deep, and the bottom's heaviness makes it painfully awkward. And don't get us started on the sunglasses.

Karen Fairchild's outfit at the May 2025 ACMs made all the styling mistakes you'd want to avoid when jumping aboard the sheer trend. She accessorized poorly, picked an unflattering cut, and chose to make her underwear visible in the most unimpressive way possible. This awkwardness is only aggravated by the stripe mismatch. We have vertical lines on the bodice that clash with horizontal ruffles on the skirt. And to top it all off, the oversized flower at the neckline looks like a throwback to the choker trend of the past (aka the outdated necklace trend we're replacing in 2025). Fairchild is stunning, but this outfit just wasn't it.

Given how proud Wynonna Judd looks in these pictures, it pains us to say this, but this Morticia Addams–inspired look is a big-time flop. Fitted blazer up top, full-on see-through boho drama below, it's two clashing vibes that never meet in the middle. The long blazer paired with flare lace pants creates a bulky silhouette, making everything look heavier and less flattering. If Judd had stuck to just one concept, she might have pulled it off.

There's sheer, there's sexy, and then there's "did you forget your dress?" Unfortunately, this leans into the last category. The fabric looks thin, cheap, and dangerously close to falling apart. It's certainly not what we expected from Kassi Ashton at all. The texture of the dress had potential — and the color could've been dreamy on a better silhouette — but this just feels unfinished. Even the hair leans more morning after than red carpet. This isn't effortless; it's just underdone. Now, read up on the worst-dressed celebs at the 2025 Academy of Country Music Awards for more fashion critiques.