The 2026 Grammy Awards red carpet had its share of standout looks. Some artists leaned fully into drama, creativity, and risk—and it worked. Others, however, missed the mark in ways that were hard to ignore. Every year, the Grammys promise bold fashion, and while that boldness sometimes pays off, it can just as easily slide into confusion, excess, or plain bad judgment.
This year, Chappell Roan dominated early fashion chatter with her striking Thierry Mugler couture piece from the designer’s 1998 spring/summer collection. The look was theatrical, intentional, and clearly thought through. Lady Gaga, as expected, delivered another headline-worthy moment in a feathered Matières Fécales dress that felt her unapologetically. These looks reminded everyone why the Grammys are known for fashion risks.
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But not everyone rose to the occasion. Some stars played it too safe, others tried too hard, and a few ended up looking completely disconnected from the moment. Below are the looks that had people cringing rather than applauding.
Miley Cyrus leaned too hard into biker energy
Miley Cyrus is usually a red carpet win, but this time, the balance was off. Dressed in Celine, she wore a black biker jacket decorated with an oversized brooch featuring her initials. On paper, it sounds edgy. In reality, it felt cluttered. The all-black palette, once a strong signature, is starting to feel repetitive, and the extra details didn’t elevate the look—they weighed it down. Sometimes less really is more, and this outfit didn’t seem to get that memo.
Doechii’s dramatic gown suffered from poor proportions
Doechii had plenty to celebrate after winning Best Music Video for her 2025 hit “Anxiety,” but her red carpet dress distracted from the moment. The custom Robert Cavalli gown featured an enormous skirt and a long train that overwhelmed her frame. While the color suited her beautifully and her hair and makeup were on point, the excessive fabric turned the dress into more of a burden than a statement. The fit simply didn’t serve her.
Jeff Kravitz/GettyAli Wong’s styling continues to miss the mark
Ali Wong’s 2026 Grammys look raised familiar concerns. Wearing a shimmering green Vivienne Westwood gown, the comedian appeared uncomfortable in a dress that didn’t quite fit. The corseted bodice looked oversized, and the short train felt awkwardly unfinished. The lack of accessories didn’t help either. After several red carpet missteps in recent years, this felt less like an experiment and more like a pattern.
Chrissy Teigen’s throwback look felt outdated
Chrissy Teigen’s outfit seemed pulled straight from a mid-2010s mood board—and not in a nostalgic way. The Caroline’s Couture dress featured a sweetheart neckline, swirling patterns, and ruched details that felt overly busy. Paired with a matching clutch and pointed heels, the look leaned heavily into prom-night energy. It wasn’t flattering, and it didn’t feel current. Instead, it brought back fashion memories most people are happy to forget.
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Bon Iver’s outfit lacked red carpet polish
Justin Vernon of Bon Iver is known for doing things his own way, and that includes fashion. Still, his 2026 Grammys look missed the tone of the event. Wearing a navy Bode suit embroidered with horses, paired with a bolo tie, outdoor-style hat, and a grocery tote bag, Vernon looked more prepared for a casual errand than music’s biggest night. Even with the political statement accessories, the overall presentation felt disjointed and oddly underdressed.
Darren Criss went theatrical, but not effectively
Darren Criss usually brings personality to the red carpet, but this year’s custom Tanner Fletcher suit fell flat. Lace detailing, a white silk top, long sleeves, and a dramatic ribbon should have added flair. Instead, the look felt oddly dull. The cream loafers didn’t add much, and the outfit lacked a clear direction. While his Grammy nomination was well deserved, the fashion moment didn’t live up to the occasion.
The Grammys are about pushing boundaries, but risk without cohesion often backfires. The worst-dressed stars of the 2026 Grammy Awards didn’t fail because they tried something new—they failed because the looks didn’t feel intentional, flattering, or suited to the moment. On a night meant to celebrate creativity, that disconnect stood out the most.
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