The American Music Awards is an annual event founded by Dick Clark in 1974 to give fans the power to decide which nominees deserve to win in each category. The awards ceremony also helps recognize and promote new emerging artists by giving them a national television stage on which to perform. Since its inception, the awards ceremony has gradually evolved into a fashion show in which artists make bold statements, with increasingly lavish outfits appearing on the red carpet after the turn of the millennium. Because there have been so many bold fashion choices made by celebrities looking to stand out, there have inevitably been countless fashion flops in the history of AMA.
While the 2026 American Music Awards were a fashion flop for these celebritiesthere have been much worse looks in the past that ended up on the AMA red carpet as a fashion train wreck. Despite the public’s fixation on celebrity women’s fashion at high-profile events, it was actually men who were most often 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 American Music Awards history.
Britney Spears and Justin Timberlake’s all-denim AMAs outfits are still being talked about
Britney Spears and Justin Timberlake defined the fashion trends of the millennium when they went all-denim at the 2001 American Music Awards. Timberlake’s Canadian tuxedo and cowboy hat combo received 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 on “The Daily Popcast” in 2020 (via People) as we look back on the memorable Y2K fit. Katy Perry and Riff Raff later recreated their all-denim styles at the 2014 AMAs in outfits made by Versace.
Chris Brown wreaked havoc on the red carpet at the 2005 AMAs
The 33rd annual American Music Awards in 2005 may have been the worst-dressed year in the awards show’s history. It was the year when brown clothing dominated the red carpet, from the boring brown dresses of Ashanti and Hilary Duff 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 oversized suit didn’t fit properly, 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 a few sizes smaller, he might have been able to avoid this fashion wreck altogether.
Nicki Minaj’s AMA outfit from 2010 was a lot to take in
While Nicki Minaj was promoting her album “Pink Friday” at the 2010 American Music Awards, she decided to wear a pink dress on the red carpet. However, it was everything on top of the bubblegum-colored garment that attracted all the attention. The mix of gold and colorful decorations formed an exoskeleton, but despite the structured arrangement, it was far too busy. “She looks like a created character from Dynasty Warriors,” said one YouTube user said. “Some people have trashed her dress, but I think the dress is unique and unique and beautiful. I like that Nicki isn’t a follower of the crowd. She proves that it’s okay 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 some of her favorite tapes were destroyed during a flood in Nashville. Although the tape gave her dress a messy look, it was her styling that made it one of the worst AMA looks of all time. Her messy mohawk and studded eyebrows were visually loud on the red carpet. “OMFG what a total disaster!! all!“A Facebook user commented on her AMA post.
Ariana Grande’s brother cowered 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 that looked like he was wearing a short-sleeved button-down and a bow tie. The paint job could have been better as it ended up reading as tacky and messy. “Was that really spray painted? I thought he was just wearing something tight and a little see-through,” said one YouTube user commented. In the comment section from one of his AMAs red carpet interviews, other YouTubers called him “a try-hard” and “a wannabe” for wearing the attention-seeking outfit.
Bad Bunny had a third eye at the 2018 AMAs
In his AMA debut, Bad Bunny showed up to the 2018 American Music Awards wearing a loud teal button-down shirt with skulls and fire printed all over. He wore black and white striped pants that contrasted with the busy shirt pattern, making his entire outfit look messy and visually overwhelming. The worst part of his AMA’s red carpet look, however, was the all-seeing eye in the center of his forehead. His disturbing third eye caused X (then Twitter) to compare him to “Dragon Ball” character Tien Shinhan and accuse him of being part of the Illuminati. While he certainly stood out, it seems like Bad Bunny made a bad first impression on many AMA fans.
Post Malone brought a red Solo cup to the AMA red carpet
Also in 2018, Post Malone had 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. However, the worst offender of this infamous look is the red Solo cup he held in his hand while gracing the AMA red carpet. He looked less like a nominated artist of the year and more like a frat boy arriving at a costume party.
Billy Porter rained on our fashion parade at the 2021 AMAs
Actor and singer Billy Porter caused an online firestorm after gracing the 2021 AMA red carpet in an all-blue suit with a cutout at the chest and an umbrella hat. The umbrella hat proved controversial, with some online users raining on his parade and accusing him of attention seeking. “I wish @joanrivers were still alive so she could give this man a new one. @fashionpolice,” one user commented on Porter’s Instagram post from the evening. “Billy looked like a complete fool with an umbrella on his head. He should ask Rue Paul how he should really dress,” another said.
Machine Gun Kelly looked like a porcupine at the 2022 AMAs
Machine Gun Kelly was dressed to kill or poke at the 2022 American Music Awards in Los Angeles, California. The “Rap Devil” wore a purple suit covered in large metal spikes sticking out 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 didn’t help viewers were in an uproar after Machine Gun Kelly’s win at the 2022 AMAs for favorite rock artist.
Shaboozey’s 2025 AMAs outfit was a plaid nightmare
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 stunning rhinestones and embroidery throughout the suit, which ultimately got lost in the mess. The matching plaid belt, jeans, black leather vest and white blouse with white bow tie were way too much for one outfit. The clash of patterns and colors was unpleasant to the eyes. “Overall the look is rodeo clown,” said one Reddit user said. “He looks ridiculous”, also an Instagram user said.
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