The American Music Awards is an annual event created by Dick Clark in 1974 to give fans the power to decide which nominees deserve to win each category. The awards 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 developed into a fashion show where artists make bold statements, where ever more outrageous outfits appear on the red carpet after the turn of the millennium. With so many daring fashion choices being made by celebrities looking to stand out, there have inevitably been countless fashion flops in the history of the AMAs.
While The 2026 American Music Awards was a fashion flop for these celebritieswere there far worse looks to hit the AMAs red carpet like a fashion train wreck in the past. Despite the public’s fixation on celebrity women’s fashion at high-profile events, it was actually the men who most often found themselves on the dreaded worst-dressed list. From Britney Spears and Justin Timberlake’s denim Y2K outfits in 2001 to Shaboozey’s plaid nightmare in 2025, these are the biggest fashion flops in American Music Awards history.
Britney Spears and Justin Timberlake’s denim AMA outfits are still talked about
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 that memorable Y2K fit. Katy Perry and Riff Raff later recreated their all-denim style at the 2014 AMAs in outfits made by Versace.
Chris Brown wreaked havoc on the 2005 AMAs red carpet
The 33rd Annual American Music Awards in 2005 was arguably the worst-dressed year in the history of the awards show. It was the year 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 who committed fashion crimes with their brown ensembles, Chris Brown was the worst offender. Every piece of his large suit was ill-fitting, making him look like a child 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.
Nicki Minaj’s 2010 AMA outfit was a lot to take in
While promoting her “Pink Friday” album at the 2010 American Music Awards, Nicki Minaj decided to wear a pink-based dress for the red carpet. However, it was all layered on top of the bubblegum colored outfit 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 looks like a made up 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 is not a follower of the crowd. She proves that it’s ok to be different“, another YouTube user came to her defense.
Kesha’s 2010 AMAs look wasn’t much better
The same year that 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 from VHS tapes after several of her favorite tapes were destroyed in a flood in Nashville. While the tape gave her dress a disheveled look, it was primarily her styling that made it one of the worst AMAs looks ever. Her messy mohawk and bushy eyebrows were visually loud on the red carpet. “OMFG what a total disaster!! the whole thing!” a Facebook user commented on her AMAs post.
Ariana Grande’s brother was shrunk in a painted-on shirt
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 bow tie. The paint job could have been better as it ended up reading tacky and messy. “Is it really spray painted? I thought he was just wearing something tight and a little sheer,” one YouTube user commented. In it comment section of one of his AMAs red carpet interviews, fellow YouTubers called him “a try-hard” and “a wannabe” to wear the attention-seeking outfit.
Bad Bunny had a third eye at the 2018 AMAs
In his AMAs debut, Bad Bunny rolled up to the 2018 American Music Awards in a heavy 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. The worst part of his AMAs red carpet look, however, was the all-seeing eye located in the center of his forehead. His disturbing third eye led X (then Twitter) to compare him to “Dragon Ball” character Tien Shinhan and accuse him of being part of the Illuminati. While he definitely stood out, it seems Bad Bunny made a bad first impression on many AMAs fans.
Post Malone brought a red Solo cup to the AMAs red carpet
Also in 2018, Post Malone suffered a major fashion flop when he wore a blue suit with a black turtleneck. The suit featured snakes with a yellow and brown pattern that clashed with the rest of the outfit’s color scheme. The worst offender of this infamous look, however, is the red Solo cup he held in his hand when he graced the AMAs red carpet. He looked less like an artist of the year nominee and more like a boy arriving at a fancy dress party.
Billy Porter rained on our fashion show at the 2021 AMAs
Actor and singer Billy Porter sparked an online storm after gracing the red carpet at the 2021 AMAs in an all-blue suit with a plunging neckline and umbrella hat. The umbrella hat proved controversial, with some online users raining down on his parade and accusing him of seeking attention. “I wish @joanrivers was alive so she could rip this guy a new one. @modepoliti“, a user commented on Porter’s Instagram post from the night. “Billy looked like a complete fool with an umbrella on his head. He should ask Rue Paul how to dress properly“, another said.
Machine Gun Kelly looked like a hedgehog at the 2022 AMAs
Machine Gun Kelly was dressed to kill, or stab, at the 2022 American Music Awards in Los Angeles, California. The “Rap Devil” wore a purple suit covered in large spikes made of gunmetal that stuck out in all directions. The uninviting outfit looked uncomfortable for the singer wearing it as he had to pose with outstretched arms to avoid being stung. He even admitted that the suit was “hard to pee in” (via People). The controversial appearance probably didn’t help matters viewers were up in arms after Machine Gun Kelly’s 2022 AMA win for favorite rock artist.
Shaboozey’s 2025 AMAs outfit was a plaid nightmare
Country music star Shaboozey reinvented himself 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, which eventually disappeared into the mess. The matching plaid belt, denim pants, black leather vest and white blouse with white bow was way too much for one outfit. The clash of patterns and colors was unpleasant for the eyes. “Overall, the look reads rodeo clown,” one Reddit user said. “He looks ridiculous“, also an Instagram user said.
