The Biggest Fashion Flops In The History Of The American Music Awards

The American Music Awards is an annual event that was created by Dick Clark in 1974 to give fans the power to decide which nominees deserve to win each category. The award show also helps recognize and promote new up-and-coming artists by giving them a nationally televised stage to perform on. Since its inception, the award show has gradually evolved into a fashion show where artists make bold statements, with increasingly outrageous outfits appearing on the red carpet after the turn of the millennium. With so many daring fashion choices being made by celebrities wanting to stand out, there have inevitably been countless fashion flops in AMAs history. 

While the 2026 American Music Awards was a fashion flop for these celebs, there were far worse looks that hit the AMAs red carpet like a fashion trainwreck in the past. Despite the public's fixation on celebrity women's fashion at high-profile events, it was actually the men who most frequently found themselves on the dreaded worst-dressed list. From Britney Spears and Justin Timberlake's all-denim Y2K outfits in 2001 to Shaboozey's plaid nightmare in 2025, these are the biggest fashion flops in the history of the American Music Awards.

Britney Spears and Justin Timberlake defined Y2K fashion trends when they showed up to the 2001 American Music Awards wearing all-denim ensembles. Timberlake's Canadian tuxedo and cowboy hat combo was met with mixed reactions, but Britney Spears' fashion flop became one of her most iconic looks. "You do a lot of things when you're young and in love," Timberlake said in 2020 on "The Daily Popcast" (via People) while reflecting back on the memorable Y2K fit. Katy Perry and Riff Raff later recreated their all-denim style at the 2014 AMAs in outfits made by Versace.

The 33rd annual American Music Awards in 2005 was arguably the worst-dressed year in the award show's history. It was the year when brown clothing dominated the red carpet, from Ashanti and Hilary Duff's bland brown dresses to the brown outfits worn by Chingy and Joe Simpson. But while there were plenty of stars committing fashion crimes with their brown ensembles, Chris Brown was the worst offender. Every piece of his supersized suit was ill-fitting, making him look like a kid trying on his father's clothes. The long clothes also made his legs look comically short. If only he had settled for something several sizes smaller, he might have avoided this fashion trainwreck altogether. 

While Nicki Minaj was promoting her "Pink Friday" album at the 2010 American Music Awards, she decided to wear a pink-based dress for the red carpet. However, it was everything layered on top of the bubblegum-colored garment that stole all the attention. The mix of gold and colorful embellishments formed an exoskeleton, but despite the structured arrangement, it was far too busy. "She look like a created character on Dynasty Warriors," one YouTube user said. "Some people bashed her dress but I think the dress is unique and unique is beautiful. I like that Nicki isn't a follower of the crowd. She proves that its ok to be different," another YouTube user came to her defense. 

The same year Nicki Minaj took a risk with her colorful exoskeleton, singer Kesha also made a bold choice for her own 2010 American Music Awards red carpet look. She decided to wear a dress made of VHS tapes after several of her favorite tapes were destroyed in a Nashville flood. While the tape gave her dress a disheveled appearance, it was primarily her styling that made it one of the worst AMAs looks of all time. Her messy mohawk and studded eyebrows were visually loud on the red carpet. "OMFG what a total disaster!! all of it!" one Facebook user commented on her AMAs post. 

Ariana Grande's older half-brother, Frankie Grande, is no stranger to trying to get people's attention. At the 2014 American Music Awards, he braved the red carpet in a painted-on shirt made to look like he was wearing a short-sleeved button-down and bowtie. The paint job could have been better, as it ultimately read as tacky and messy. "Is that really spray-painted? I thought he was just wearing something tight and a little see-through," one YouTube user commented. In the comment section of one of his AMAs red carpet interviews, other YouTubers called him "a try-hard" and "a wannabe" for wearing the attention-seeking outfit.

In his AMAs debut, Bad Bunny rolled up to the 2018 American Music Awards in a loud teal button-down shirt with skulls and fire printed all over it. He wore black and white striped pants that clashed with the busy shirt pattern, making his entire outfit look messy and visually overwhelming. However, the worst part of his AMAs red carpet look was the all-seeing eye placed in the middle of his forehead. His unsettling third eye had X (then Twitter) comparing him to "Dragon Ball" character Tien Shinhan and accusing him of being a part of the Illuminati. While he definitely stood out, it seems that Bad Bunny made a bad first impression on many AMAs fans.

Also in 2018, Post Malone suffered a major fashion flop when he wore a blue suit with a black turtleneck. The suit featured serpents with a yellow and brown patterning that clashed with the rest of the outfit's color scheme. However, the worst offender of this infamous look is the red Solo cup he held in his hand as he graced the AMAs red carpet. He looked less like an artist of the year nominee and more like a frat boy arriving at a costume party.

Actor and singer Billy Porter kicked up an online storm after gracing the 2021 AMA red carpet in an all-blue suit with a chest cutout and umbrella hat. The umbrella hat proved controversial, with some online users raining on his parade and accusing him of attention seeking. "I wish @joanrivers was alive so she could rip this guy a new one. @fashionpolice," one user commented on Porter's Instagram post from the night. "Billy looked like a pure fool with an umbrella on his head. He should ask Rue Paul how to dress for real," another said.

Machine Gun Kelly was dressed to kill, or poke, at the 2022 American Music Awards in Los Angeles, California. The "Rap Devil" sported a purple suit covered in large spikes made of gunmetal protruding in all directions. The uninviting outfit looked uncomfortable for the singer wearing it, as he had to pose with his arms outstretched to avoid being poked. He even admitted that the suit was "hard to pee in" (via People). The controversial look probably did not help the fact that viewers were up in arms after Machine Gun Kelly's 2022 AMAs win for favorite rock artist.

Country music star Shaboozey found himself on the worst-dressed stars at the 2025 American Music Awards list after arriving on the red carpet in a plaid nightmare. His yellow, white, and brown plaid chaps and jacket were already busy, but he added bedazzled rhinestones and embroidery throughout the suit that ultimately got lost in the mess. The matching plaid belt, denim pants, black leather vest, and white blouse with a white bowtie were far too much for one outfit. The clashing of patterns and colors was unpleasant on the eyes. "Overall, the look is reading rodeo clown," one Reddit user said. "He looks ridiculous," an Instagram user also said.