Some celebrities pick a style, a signature look that will make them instantly memorable and recognizable. But not Miley. Change is her only constant. She is forever changing, growing, evolving, and so are her looks. One day, Miley Cyrus wears haute couture, the next day she opts for latex outfits that resemble an arts and crafts project. The next time you see her, she’ll be dressed as a classic Hollywood icon, and then she’ll transform into a rock diva. There is no stopping when it comes to Miley Cyrus. You can’t box her in and put a label on her. So let’s take a look at some of her truly showstopping award-show looks.
The 2009 Oscars look that quietly announced she was no longer just Disney’s girl
This wasn’t Miley’s first Oscar red carpet (it was actually her second), but this was the first time she showed us that she’s not here to blend in, she’s here to stand out. This was a time in her life when she was transitioning from a Disney star to a grown woman. It was her first statement look and, if you think about it, this was the first sign that Miley loves to make an entrance, she loves the drama of it all. The sparkly Zuhair Murad gown was a great choice to set herself apart, start a new fashion era, and also put a new designer on the map. Murad later said that it was a big moment in their career when Miley wore that dress.
The 2013 VMAs teddy-bear look was weird, loud, and more intentional than people realized
A lot of things happened for Miley at the 2013 VMAs. When she arrived at the event, she was dressed in a black bejewelled two-piece set by Dolce & Gabbana. It looked fairly conservative, and no one could’ve expected what would happen on stage late and what she would be wearing.
Once it was time to perform, Miley showed up on stage in a grey, shaggy teddy bear-looking leotard. Many people thought it was just a weird Miley look, but Cyrus later explained that it was a look inspired by a Todd James sculpture that reminded her of herself. So it was supposed to be symbolic, and her next transformation was meant to symbolize a rebirth.
Then she doubled down with the nude latex performance look
We all remember what happened next: Miley stripped off the teddy bear look to stomp the stage in a part of what can only be described as skin-colored latex underwear and a foam finger. She danced, she stuck her tongue out, she twerked on Robin Thicke. It was scandalous and made a lot of people uncomfortable. Although Miley received significant criticism for that stunt, she stated that this singular moment profoundly changed her life and inspired her to create the Happy Hippie foundation, as she wanted to use the attention she received for a positive purpose.
Her 2013 EMA bodysuit proved she was not done making headlines internationally either
You’d think she can’t top the VMA’s but it’s Miley we’re talking about. She showed up at the 2013 MTV Europe Music Awards in Amsterdam in a white skintight revealing bodysuit and a fur stole, paired with matching platform heels. But the outfit wasn’t the main event on the evening, she then went on to light a joint on stage while accepting her award for “Wrecking Ball.”
Many people thought she was trying to make a statement, but Miley later said that she didn’t even think of it as a big deal, she just thought that the audience in Amsterdam would find it funny. People are going to talk no matter what, so Miley just casually gave them more to talk about, just for giggles.
The 2019 Grammys brought a sleeker, more grown-up version of Miley
2019 was very different from 2013 for Miley. When she walked the red carpet at the Grammy’s she wore a much more sophisticated outfit than we were used to. She opted for a black Mugler suit. Yes, she wore the jacket without anything underneath, which certainly added a daring touch, but it was a significant departure from her VMA appearance. This was sexy, but in a grown-up, sophisticated way.
For her performance, Miley changed from the jacket to an even more risqué vest that was held together by a strategically placed chain.
However, after the performance, she changed into a black Jean Paul Gaultier piece. It was an archival black dress that had sheer panels and looked absolutely stunning. It was definitely a huge style shift for Miley, who later admitted that she used to think sophisticated looks were boring, so they just didn’t suit her because she didn’t feel old enough for that style and thought she would look ridiculous and like she’s trying too hard to look older. However, it is evident that Miley can effortlessly pull off any look she desires.
The 2024 Grammy’s red carpet look was basically fashion armor made of safety pins
While Miley’s style definitely shifted over the years but she still loves a good fashion moment. And that was exactly what she served at the 2024 Grammy’s. She wore a John Galliano for Maison Margiela dress that looked like it was made solely out of gold safety pins masterfully interlocked into a look that was basically fashion armour and yet barely there.
It was a great choice for the night, since Miley was nominated in a few categories and won Best Pop Solo Performance and Record of the Year, both for her hit “Flowers.” It was the first time that she won a Grammy, which is kind of strange considering how long she’s been at it.
But this wasn’t her only outfit at the Grammy’s. Throughout the night, she also changed into a glorious sheer black catsuit and a brown sequin dress with an impossibly high leg slit by Gucci. She made all of these outfits even more dramatic by wearing her hair in a 70’s feathery, ultra-voluminous hairdo.
Her 2024 Grammy performance dress was pure sparkle and pure Miley
The dress she actually wore for her performance was also a showstopper. It was a sparkly Mackie dress that was giving showgirl, it was playful with all the dangling beads and jewels reflecting stage lights as Miley took the stage. Miley made the moment even more memorable by changing the song lyrics to “Started to cry, but then remembered—I just won my first Grammy!” It was fun and cheeky and a very Miley thing to do.
The 2025 Grammy’s leather Saint Laurent gown was daring but much more controlled
Miley went dark, sleek, and vampy for the 2025 Grammy’s in a black leather Saint Laurent dress with cutouts. But what caught people’s attention more than her dress was her hair. Somehow it became Miley’s “disaster do” of the night. No one could determine whether her hairstyle was the result of a bad haircut or something else. It was later said that the hair was intentional, but everyone called it Miley’s “disaster do.” Either way, Miley couldn’t care less, since she walked away from that night with another Grammy thanks to her collaboration with Beyoncé.
The 2025 Oscars look proved that sometimes the outfit is not even the main story
Miley wore a gorgeous glittering black Alexander McQueen gown to the 2025 Oscars. But once again it wasn’t even the dress that got the most attention. It was Miley’s bleached brows that got the people talking. It was definitely an unusual combo. Some media outlets described the dress and perfectly coiffed old-Hollywood hair as an almost perfect look if not for the brows. People online described this combo as experimental and giving glam goth vibes.