The Most Inappropriate Outfits Miley Cyrus Has Ever Worn

Former child star-turned-pop icon Miley Cyrus has experimented with several different identities throughout her career. The musician got her start on the Disney Channel, leading a double life as Miley Stewart and the titular pop star on "Hannah Montana." She showcased her acting prowess in teen flicks before fully transitioning to music in the 2010s. Breaking out of her Disney image in 2013 with her album "Bangerz," Cyrus' style drastically changed and did a shocking 180.

Miley Cyrus' style evolution is arguably the most drastic in Hollywood. The "Flowers" singer went from '00s bohemian to punk with a platinum pixie. The 2020s have been reserved for a subtler look, bringing back her long, brunette hair and integrating a classic Hollywood glam into her wardrobe. But before that, Cyrus dared to wear a cartoon bear bodysuit to the VMAs and swing from wrecking balls completely naked. These were totally left-field moves from the once beloved children's pop star, which is why many of her outfits were deemed ill-fitting for the respective occasions. From donning deceased rappers on a bodycon dress to nearly-naked looks, here are the most inappropriate outfits from the "Party in the U.S.A." hitmaker.

Miley Cyrus isn't afraid to show a little side boob, under boob, front boob — and quite frankly, full boob — when choosing an outfit. However, her mom, Tish, isn't obsessed with her daughter's tendency to be revealing, especially when pasties are involved. After Cyrus donned two black nipple covers under a white mesh dress at the iHeartMusic Festival in 2013, Tish voiced her disapproval. "That's the only one I really didn't like," she said in an E! News interview. When Cyrus sported a pair of ice cream pasties the following year, Tish told Page Six, "She's done it once before, and I've said before that's my least favorite outfit."

Miley Cyrus has been accused of appropriating Black culture more than once. The "Wrecking Ball" singer walked the 2013 MTV European Music Awards red carpet in a tight-fitting minidress, emblazoned with the faces of deceased rappers Tupac Shakur and Christopher Wallace, aka Biggie Smalls. The NY Vintage dress, with a laced-up front, also read, "Please stop the violence" — and many people were enraged. Global Grind argued that the fashion statement was naive and "destructive." No matter Cyrus' intention, the outfit didn't communicate her message the way she wanted.

Her dreadlock extensions weren't the only reason Miley Cyrus sparked controversy for her 2015 VMAs outfit. The "LOL" actor sported a revealing, metallic, buckled suspender dress by Atelier Versace while posing on the red carpet. The silver number featured nothing but strips of fabric at the bodice, and chandelier-like jewels draped to form a skirt. Her provocative look had more tongues wagging than her own. While many were holding their breath over whether Cyrus would have a nip slip on the carpet, she really left nothing to the imagination when she accidentally flashed the camera backstage later that night — according to Rolling Stone, the Federal Communications Commission got an earful that night.

Later that night at the 2015 VMAs — which ultimately showcased many of Miley Cyrus' most head-turning award show looks — the singer gave candy button realness when she slipped into a cellophane shift dress, covered with ballpit-esque, three-dimensional circles. She accessorized with André Courrèges sunglasses and white go-go boots. The stage ensemble was as risky as it was revealing. Photographers snagged some NSFW pics at certain angles, as evidenced by a censored image that Us Weekly published. Her stylist, Simone Harouche, might want to advise that Cyrus wear a bodysuit in her skin tone underneath next time, so as not to trigger the ire of the Parents Television Council (who were, indeed, not happy).

She joked it was chilly in the studio when Miley Cyrus visited "Jimmy Kimmel Live" in 2015, as during her appearance, the music legend didn't have a shirt. Instead, she rocked heart-shaped pasties and a shawl and skirt set with rainbow-colored sequin shards. Cyrus' outfit was so shocking that she even had Jimmy Kimmel blushing. "I am embarrassed now," said Kimmel, trying to figure out where to look. Cyrus did note that her more revealing outfits are a confidence booster, as they make celebrities, such as Paul McCartney, "uncomfortable." It seems like she's adopted the inverse of the old adage about picturing the audience in their underwear.

Miley Cyrus' 2015 VMAs wardrobe malfunction didn't shake her confidence to wear dangerous stage costumes. In 2021, the multi-time Grammy recipient wore a tattered, metallic two-piece Akna set on stage during a New Year's Eve performance. 

Miley Cyrus had wardrobe malfunction at her New Year's Eve Partyhttps://t.co/To3azNlZ2E#mileycyrus pic.twitter.com/5eey66YCX5

— Miley Cyrus Fan Club (@mileycyruspress) June 3, 2023

At one point, Cyrus swiftly grabbed her top, seemingly ensuring it covered her breasts after it started to slip. However, she ultimately let it go and performed topless, not flashing the crowd by facing away from them as she left the stage. When she came back in a red blazer, she cheekily noted: "I'm still in the most clothes that I've ever worn on stage" (via E! News).