The Worst-Dressed Celebs At The 2026 Grammy Awards Had Us Cringing

The 2026 Grammy Awards red carpet featured a lot of gorgeous dresses and bold, stylish menswear, but with them also came some real fashion disasters. Every year, various artists come together to celebrate the best music in their wildest, most creative, and audacious red carpet looks. Chappell Roan led the conversation this year with her provocative ensemble designed by the legendary Thierry Mugler from his 1998 spring/summer couture collection. Roan was nominated for record of the year and best pop solo performance for her song, "The Subway." "We've seen Chappell in so many campy, over-the-top looks, and I think that with the fake tattoos, the prosthetics, and the dress, we discussed doing something a little more sultry — a little more real," her makeup artist, Andrew Dahling, excitedly told Elle ahead of the ceremony on February 1.

Jeff Kravitz/Getty

As he gushed, "It's a Mugler medieval fantasy for the carpet." There was also our queen Lady Gaga, who slays year after year in her stunning creations and, for the 2026 event, donned a truly iconic Matières Fécales dress made entirely out of feathers. But alas, some artists were less willing to break the mold and take risks than others. Blackpink's Rosé, who was nominated for three Grammy awards this season, opted for an understated look that left us utterly bored, to be frank. Meanwhile, 10-time Grammy-winner Billie Eilish also played it safe with her preppy-chic look courtesy of Hodakova. Below are our picks for the cringiest and worst-dressed stars on music's biggest and most fashionable night. 

Look, we love Miley Cyrus as much as the next person and think she's the epitome of cool, but unfortunately, this outfit just wasn't doing it for us. Wearing Celine on the red carpet, including a black biker jacket adorned with a giant brooch bearing her initials "M" and "C," the pop star's look just had way too much going on. As Coco Chanel famously quipped, "Before you leave the house, look in the mirror and take one thing off." Miley clearly didn't heed her advice. The all-black ensemble is starting to get predictable and tired, too, at this point. 

Congratulations to Doechii for winning best music video for her hit 2025 song "Anxiety," but her ill-fitting prom dress on the Grammys red carpet didn't exactly leave us impressed. Her custom Robert Cavalli gown featured a voluminous skirt with a floor-sweeping train that dragged after her like a king-sized comforter. She looked incredible with her natural hair and makeup, and the color of her dress was gorgeous against her skin, but she could've done without all that extra fabric.

After this and the monstrosity that was her look at the 2025 Golden Globes, it might be time for Ali Wong to consider firing her stylist and hiring a new one. Nominated for best comedy album for her Netflix special "Ali Wong: Single Lady," the comedian and actor turned up to the 2026 Grammys in a shimmering green dress by Vivienne Westwood. It had a corseted bodice that looked to be a little too big for Wong's petite frame, and a too-short train. Perhaps some jewelry might have saved this outfit, but overall, not her best moment. 

Chrissy Teigen took us back to the era of flower crowns and Snapchat filters with her 2026 Grammys look, which was very much giving prom dress gone bad. Her look, designed by Caroline's Couture, featured a sweetheart neckline with swirl patterns and ruched hems on one side, giving fans a nice view of her gorgeous pins (or should we say pin?). Teigen paired it with silver earrings, a matching maroon clutch, and some pointed toe heels to complete her ensemble. Just terrible all 'round. 

As much as we appreciate Justin Vernon, aka Bon Iver, for standing up to President Donald Trump amid his brutal ICE crackdown in Minnesota, this look was absolutely horrendous. The celebrated indie folk singer, who's memorably collaborated with Taylor Swift on several occasions, donned a custom navy suit by Bode featuring embroidered horses and an "ICE OUT" pin and orange whistle on his lapels. With Vernon's bolo tie and outdoor style hat, the Grammy winner looked as though he was cosplaying as a national park ranger. The grocery tote bag and tan loafers were certainly not of much help, either.

We can always count on Darren Criss to bring the drama and fun to every red carpet, but this time, he totally dropped the ball. For the 2026 Grammy Awards, the actor rocked a custom suit by Tanner Fletcher with lace detailing over a white silk top, long sleeves, and a statement ribbon. He finished it off with cream loafers, which didn't add much oomph to this (frankly) dull ensemble. But congratulations on his first Grammy nomination for best musical theater album this year! The recognition — much like Criss' spot on our worst-dressed list — was certainly well deserved.