The Absolute Worst-Dressed Celebrities At The 2025 Grammys

The usual glitz and glamor of awards season was off to a rocky start in 2025, with the gut-wrenching fires in Los Angeles pushing much of the film industry’s celebrations back a few weeks. Luckily for music makers, the Grammys went ahead on schedule and were able to bring out the celebrity masses. Looking for a chance to show off fashion statements that push the boundaries, many musicians went for see-through looks, mesh cutouts, and even Victorian-era throwbacks. Some nailed it more than others, however.

With the return of repeat host Trevor Noah not making any digs at Will Smith this time, things seemed back to normal for many of the stars in attendance. Costume changes were expected for performers going from the red carpet to the stage, but the camera never forgets. Whereas some stars nailed it in their live performances, their looks upon arrival were a different story. Here are some of the absolute worst-dressed celebrities at the 2025 Grammys.

Arriving at the ceremony boasting seven nominations, Billie Eilish was in good company with her brother and producer, Finneas O’Connell, by her side. However, while walking the red carpet, Eilish could have almost been mistaken for a different Billy — Billy Bob Thornton. Wearing a look similar to Angelina Jolie’s wildest ex’s nearly unrecognizable Golden Globes ensemble, Eilish was decked out in a wallet chain, a boxy jacket, a strange hat, and tiny sunglasses. The whole look was a bit of a hot mess express — though a decent homage to Eilish’s tomboy style.

Eilish wisely switched up the look to sing “Birds of a Feather” as a tender tribute to Los Angeles. “We love you L.A.,” Eilish exclaimed at the end of her performance.

With many celebrities losing their homes to the Los Angeles wildfires, most of the performances and general vibe of the evening were dedicated to supporting recovery efforts — which makes Jaden Smith’s red carpet outfit feel incredibly out of place and possibly inappropriate. Wearing a ramshackle effort of a miniature house on his head, Smith waltzed into the ceremony as a walking reminder of something many people have lost. Not really the right message to be sending, to be honest. It also looked very silly.

Jaden Smith was there to accompany his sister, Willow Smith, who was nominated for two awards — best engineered album for “Empathogen” and best vocals, arrangement, and instrument for “Big Feelings.” Hopefully, her brother’s antics don’t deter her from success.

Whereas the tragic yet fan favorite Chappell Roan wore a Victorian-era inspired outfit that absolutely nailed it, Sierra Ferrell was not so lucky in her choices. The white embroidered gown had just a bit too much going on. As much as we love a statement piece, this had too many statements to make. The scepter, the beaded headpiece, the puffy plumes around the neck — it was all just too much.

This didn’t stop Ferrell from winning big that night. The singer from Charleston, West Virginia, won four awards ranging from americana album to American roots song.

Capitalizing on a true brat moment, Charlotte Emma Aitchison — who goes by the stage name Charli XCX – stepped into the Grammys donning boots fit for the gladiator ring and a dress ready to make a swan song. The fit of the dress was interesting enough — the ruffles, the corset — but the cut by her hips gave a bulky appearance, with the tulle seeming to be making an escape from her hips instead of being a cohesive part of the piece. Combined with the knee-high, peekaboo boots, the overall look felt more like a costume that was rejected from “Poor Things” than something the notorious party girl would wear to the club.

The outfit did not deter Charli XCX from winning her first Grammy award, however. The “Girl, So Confusing” singer took home the trophy for best dancePop recording for “Von Dutch,” while “Brat” won best dance/electronic album.

Embattled artist Kanye “Ye” West and his wife, Bianca Censori, made a rare public appearance at the 2025 Grammys. In what has become a bit of a tradition, Censori wore an inappropriate outfit, while West was dressed in clothing bordering on the overtly casual. Both of them were underdressed in their own ways. West, in his workman’s attire, was not red carpet-ready, and Censori was basically nude under her black fur coat. Both looks were a misstep, with West’s ex, Julia Fox, wearing an outfit that was a combination of the two — and campier to boot.

Luckily, there was no other awkward behavior from West or Censori that night. West was able to successfully avoid running into Taylor Swift and reigniting the feud between the two of them.

When country artist Collins Obinna Chibueze, who goes by the stage name Shaboozey, took the stage to perform a medley of “Good News” and “A Bar Song (Tipsy),” he looked absolutely immaculate in his brown two-piece suit with folk-inspired detailing. The same cannot be said for what he wore on the red carpet. Wearing an eerily matte yet still shiny silver suit jacket and scarf that felt like several pieces of 3D-printed plastic strung together, the “My Fault” singer was not rocking his best look at the start of the evening.

Notably, Shaboozey was able to collaborate with Beyoncé on her album “Cowboy Carter,” which successfully snagged the trophies for best country album and album of the year. A win we can all get behind.

While many stars wore see-through mesh ensembles, some wore them better than others. Attending the awards ceremony with her husband, John Legend, Chrissy Teigen tried to fit in with the crowd but ended up looking a bit of a mess. The black zipper-like structures holding everything precariously in place gave a rather cheap vibe to the whole piece instead of elevating it. And the black mermaid-inspired train felt held together with wires instead of elegant and flowing.

To be fair, it is always cute to see Teigen and Legend going on a nice little date night together — letting their kids live the lavish life without them for a change. Legend performed in the opening musical number with heavy hitters like St. Vincent and Sheryl Crow, smiling the whole time.

From the waist down, country singer Kacey Musgraves’ Grammys look was stunningly appropriate for the event. The same cannot be said for the top half. Wearing a plain white tank top at an event where your peers are opting for haute couture is certainly a choice. Overall, it made the “Happy and Sad” singer look a bit too casual for the events of the evening. One of the things Musgraves has tried to keep behind the scenes is her discomfort with fitting into the current state of the folk and country music scene. 

However, the Grammy Awards would beg to differ with her. Even though she didn’t wear the appropriate attire for the event, it did not halt Musgraves from walking away with the best country song award for “The Architect.”

Petite powerhouse Sabrina Carpenter has been known to channel some vintage Hollywood styles, usually to fantastic effect. This time, however, she missed the mark. This silk and floofy piece looked just a little cheap, with the shine being a bit too harsh and the feathers appearing sort of fake. The classic Hollywood style is hard to nail, but Carpenter was able to pull out all the stops with her live performance.

Wearing cohesive and matching outfits while she performed “Please Please Please” and “Espresso,” Carpenter was able to dazzle the crowd and remind them why she was already a winner going into the evening. She had already snagged the best pop solo award for “Espresso” earlier in the evening, rounding out quite a transformative year for the pop princess.