Miley Cyrus Award Show Looks That Had Heads Turning

Miley Cyrus is one of the most unique stars in all of Hollywood. She comes from the famous Cyrus family, but she's now more recognizable than anyone else who shares her last name. While Cyrus' fame is definitely because of her talent, it's also because of her personality. The star has never been afraid to be herself, no matter the version, and she's expressed herself through her actions, her words, and her clothing.

While Cyrus has worn plenty of controversial outfits that've caused a stir, she's also become a prominent figure in fashion. This is in part due to her approach to her wardrobe. "A lot of celebrities are very concerned with their fixed image, but Miley is a chameleon. ... She's a person who loves change, and she understands that fashion is only fashion if it changes," Cyrus' longtime hairstylist, Bob Recine, said of the star to Harper's Bazaar. Because of her willingness to take risks — a quality she's had since she was a teenager — Cyrus has gotten everyone talking about her fashion choices countless times throughout her career.

These are some of Miley Cyrus' award show looks that had all of us turning our heads.

Miley Cyrus' transformation from child actor to singer-songwriter has been nothing short of incredible. Thanks to her role in "Hannah Montana," Cyrus began snagging invitations to some of the most exclusive events on the planet, including the Oscars. She first attended the famed ceremony in 2008, and she even garnered an interview with the legendary Regis Philbin. "Everything's been just a big whirlwind with the movie and the tour, but it's all been so great and successful. Most of all it's been fun," Cyrus told Philbin of her life at the time. Cyrus wore a red Valentino gown that evening, and she told the late television host that she felt like a princess in the dress.

While Cyrus certainly turned heads at her first Oscars appearance, she was even more stylish at her second. In 2009, the actor wore a sparkly, floor-length gown by Zuhair Murad that wasn't just memorable for the star — it actually launched the designer's career. "Many, many, many celebrities at the same time start wearing my clothes, but the biggest occasion, the first one, was Miley Cyrus at the Oscars," Murad said in an interview (via People). It was clear from then on that Cyrus was going to make waves with her sartorial choices.

Miley Cyrus stepped into a completely new era in 2013. The artist was clearly determined to shed her Disney persona, and she did so with new music and controversial performances. At the 2013 MTV Video Music Awards, Cyrus performed a medley of hits, including her own song "We Can't Stop" and "Blurred Lines" with Robin Thicke. While Cyrus started the performance in a different outfit (more on that later), she finished it in a nude latex bralette and panty. Cyrus completed the ensemble with a foam finger and a pair of tennis shoes, and she completed the performance by twerking on Thicke. Between the dance moves and her outfit, it was hard to say which garnered Cyrus more attention.

Cyrus' performance was all anyone could talk about the next day, and it totally altered her life and career. While Cyrus got plenty of negative attention for the moment, it also brought some good to her life. "Not only was culture changed, but my life and career were changed forever ... It inspired me to use my platform for something much bigger," she told Wonderland (via Just Jared). "If the world is going to focus on me and what I am doing, then what I am doing should be impactful and it should be great. It encouraged me to be more involved, which then led me to start my own organization, which is the Happy Hippie Foundation. It's dedicated to fighting injustice for vulnerable populations."

As noted, the latex getup wasn't the only ensemble Miley Cyrus wore for the 2013 MTV Video Music Awards. She began her VMA performance wearing a teddy bear costume, which also got people talking. The gray, shaggy costume featured metallic silver panels and a pink bear with its tongue out — a gesture Cyrus mimicked repeatedly throughout her performance. Once Robin Thicke appeared on stage, she stripped the bear costume to reveal the latex ensemble underneath.

As Cyrus has since shared, the look  was far more meaningful than anyone realized at the time. "This teddy bear costume, which was extremely controversial and made a lot of people angry ... was inspired by a Todd James sculpture that I had fallen in love with. The bear reminded me of myself for some reason. I thought it was beautiful, and I had my own custom bear by Todd James made for me that I could be inside of and be birthed, which was what was happening. It was a rebirth," Cyrus told British Vogue.

What made the outfits Cyrus performed in even more surprising was the fairly conservative ensemble she wore on the red carpet. The singer arrived in a black two-piece set bedazzled with multi-colored jewels, made by Dolce & Gabbana. Viewers who expected her to wear something similar during her performance were undoubtedly shocked.

Miley Cyrus hasn't limited her jaw-dropping fashion moments to awards shows in the United States. Not long after her headline-making appearance at the MTV Video Music Awards, Cyrus made an equally jaw-dropping appearance at the 2013 MTV Europe Music Awards. The singer went on stage in a barely-there, skin-tight bodysuit and fur stole, which she paired with some platform heels. In true Cyrus fashion, though, her outfit wasn't even the most controversial part of her appearance at the EMAs. As an accessory to her revealing outfit, Cyrus carried a joint with her on stage.

This led many to wonder whether Cyrus was indeed smoking marijuana and if she planned to bring it with her on stage. The singer later confirmed that while it was indeed the aforementioned substance, she didn't plan anything ahead of time. "I was just walking out of my room and then I was like, 'Oh, I have this in my bag. That will be really funny.' And I didn't say anything to anybody. It's not that I think about that ... and I don't tell anyone I'm gonna do it," Cyrus told The Hollywood Reporter. "Some people I think overthink so much. ... That's not why I do it. I just did it mostly because I knew the fans in Amsterdam would love it, and they started going crazy when I did it," she added, noting that she doesn't search herself online because she doesn't care what others have to say about her.

Miley Cyrus' stunt at the 2013 Video Music Awards didn't ruin her relationship with MTV. If anything, it made her more popular with the network. In 2015, Cyrus took on hosting duties for the iconic awards show, and she hit the red carpet in a very revealing getup. The ensemble featured metallic straps that covered only what can't legally be seen in public while the skirt was just some carefully draped jewels. Despite Cyrus' track record with awards shows outfits up to this point, particularly at the VMAs, this look certainly garnered Cyrus some attention. Although, that may have been helped along by Cyrus' iconic feud with Nicki Minaj, which made its way on stage that year.

Days before to the show, Cyrus was asked about Minaj and did not hold back her true thoughts about the rapper. "What I read sounded very Nicki Minaj, which, if you know Nicki Minaj is not too kind. It's not very polite. I think there's a way you speak to people with openness and love. You don't have to start this pop star against pop star war," Cyrus said in an interview with The New York Times. While on stage at the VMAs, Minaj addressed Cyrus' comments. "Back to this b**** that had a lot to say about me the other day in the press; Miley, what's good?" Minaj said. It's unclear where exactly the two stand today, but the moment was surprising enough at the time to account for even more media coverage than what was given to Cyrus' fashion that evening.

Just a few years after Miley Cyrus ended her iconic, albeit controversial, MTV Video Music Awards run, the singer truly started to come into her own fashion-wise. In 2019, Cyrus was one of the artists tapped to perform at the Grammys. She sang a duet with Shawn Mendes and walked the red carpet in a black Mugler suit, making for a much less rebellious red carpet moment than she'd become known for. After her performance, though, Cyrus didn't put the Mugler suit back on — instead she changed into a black dress made by Jean Paul Gaultier. The structured piece featured some sheer bejeweled panels, as well as a screen that went up around Cyrus' neck, making for one of the most unique dresses seen at that year's event.

Cyrus loved the dress, and she was just as fond of it in retrospect. "This is archival museum quality," Cyrus boasted to British Vogue about the dress. The piece also served as a transition for Cyrus, who's since opted for more refined looks. "At one time I thought if fashion felt sophisticated, it felt boring, or it felt beyond my years and it wasn't my time yet, or I was too young, or wanted to be too sexy to actually lean into something that felt mature," she said. "I also really liked it because it did work as a privacy screen. You always feel better when you know that you just look sickening," she added.

Although Miley Cyrus has matured in her outfit selection a bit, the singer hasn't completely changed. She still loves a daring fashion moment, especially when it's made by a great designer. For the 2024 Grammy Awards, Cyrus arrived at the ceremony wearing a golden John Galliano for Maison Margiela dress. The piece was made of safety pins all carefully arranged in geometric patterns, making for a bold yet sophisticated statement outfit. Cyrus was already garnering attention heading into the night as she was nominated in multiple categories for the work she had released the year prior, and many were curious to see how she'd fare as she'd never won a Grammy.

It turned out to be a successful night for Cyrus. The artist walked away with awards for Best Pop Solo Performance and Record of the Year, both for her hit "Flowers." Winning was a long time coming for Cyrus, and she expressed her confusion over never having won prior to 2024. "No shade, but I've been doing this for 20 years, and this is my first time actually being taken seriously at the Grammys? I've had a hard time figuring out what the measurement is there, because if we want to talk stats and numbers, then where the f*** was I? And if you want to talk, like, impact on culture, then where the f*** was I?" Cyrus mused to W magazine in a subsequent interview.

Miley Cyrus can't help but make heads turn. It's in her nature. As noted, Cyrus wore multiple outfits over the course of the evening at the 2024 Grammy Awards, with her second ensemble coming for her performance. The singer performed her hit song "Flowers" for the crowd in a metallic dress that featured all sorts of dangling beads and jewels. The outfit paired perfectly with her up-tempo performance, which she made even more exciting to watch by changing the lyrics of the song to reflect her newest achievement. "Started to cry, but then remembered — I just won my first Grammy!" Cyrus sang. Ever one to ask for more, Cyrus cheekily said to the somewhat lifeless crowd, "Why are you acting like you don't know this song?"

While Cyrus and her many ensembles (she rounded out the night with a fourth and fifth outfit — a black catsuit and a brown sequined dress) were certainly of note that evening, her hair might've gotten even more attention. Cyrus rocked a big, feathery, '70s-inspired hairdo for the Grammys that year, and it triggered lots of opinions. The singer-songwriter's hairstylist, Bob Recine revealed the goal of the look in a statement provided to Allure. "For the Grammys, we decided we wanted something dry and bigger, more fuller hair, but sexy and tousled and touchable," he explained.

Miley Cyrus has become somewhat of a modern fixture at the Grammy Awards. After performing and taking home two awards in 2024, Cyrus attended the 2025 ceremony as both a nominee and a presenter. Though she changed into a separate black dress to present the award for Record of the Year, Cyrus first arrived in a black leather Saint Laurent gown with a dramatic cut out around her chest. In addition to drawing the attention of viewers with her outfit, "Cyrus' "disaster do" certainly turned heads too. However, the hair was entirely intentional. "Since we knew her dress had an open back, we wanted to highlight her natural length by allowing strands to drape down her bare back," Cyrus' hairstylist, Bob Recine, told Harper's Bazaar. "I imagined icon Brigitte Bardot and her bangs framing all around her face."

Hair aside, Cyrus shared a supportive message to all artists the next day, plenty familiar with her work going unrecognized by the Recording Academy. "Having your name called is an honor that deserves to be celebrated. Just remember for those who don't, nothing can take away the love and devotion you put into your art. I celebrate the unrecognized artists that created something beautiful and shared it with us," Cyrus said on Instagram after the ceremony. She didn't end the post without recognizing her own achievement, though — Cyrus won her third Grammy Award that evening thanks to her collaboration with Beyoncé on the song "II Most Wanted." "Thank you [Beyoncé] for inviting me to be a part of your iconic Cowboy Carter era. Love you forever," Cyrus wrote.

Miley Cyrus knows how to keep things interesting. While she usually has heads turning thanks to her outfits, when she arrived at the 2025 Oscars to present an award, her bleached eyebrows definitely made a statement. The singer also had on a stunning black gown made by Alexander McQueen and Old Hollywood-style coifed hair, which would have been perfect if not for the brows.

Like many who attend the Oscars, though, Cyrus didn't stay in the same outfit all evening. After the ceremony, the singer changed into a black Maison Margiela gown for the Vanity Fair after-party. The eyebrows, of course, remained the same.

While most of the commentary of the night was about the various looks, Cyrus' comments were reserved for the event itself. "Congratulations to all of the nominees and winners at tonights [Oscars]. The show was moving, hilarious & inspiring. Thank you for inviting me to present best sound, a category close to my heart," Cyrus said on Instagram after the event.