Miley Cyrus has been in the public eye for almost two decades, but the multi-hyphenate has been through so many different style phases, it’s hard to believe how she’s fit everything into that time. Starting off as a young Disney starlet, Cyrus is responsible for providing us with some quintessential early aughts looks (we’re talking dresses over jeans, sequin overload, you know the deal). From there, she quickly matured and started getting offers from major labels to dress her for events, and by the time Hannah Montana: The Movie came out, she was attending the premieres in Hervé Léger and Dolce & Gabbana. It was around 2012, after she filmed The Last Song and started dating Liam Hemsworth, though, when she really started having fun with style, trying different aesthetics on for size and playing around with her hair. Just a year later, we would be introduced to the blonde, cropped hair Miley, who preferred leather sets and skin-barring looks. Then, 2015 brought us into the Bangers era filled with bondage-style tops, a whole lot of glitter, and over-the-top everything. After that, Cyrus toned it down a bit and embraced a simpler aesthetic, finding some of her preferred designers like Saint Laurent, Mugler, and Stella McCartney.
These days, the singer rarely wears anything made in the past two decades, preferring vintage pieces from the days of Gianni Versace and Bob Mackie. It’s likely this is the look that will usher us into Cyrus’ latest era, which she began with the release of “Flowers”. The singer opted to wear a vintage Yves Saint Laurent dress in the song’s music video, and the retro trend continued through out the promotion of her Endless Summer Vacation album. Let’s take a look back at some of the singer’s best red carpet looks from over the years. And make sure you buckle up, it’s a bit of a wild ride.
2023: Gucci Party
Gucci hosted an exclusive party in Beverly Hills to celebrate Cyrus’s Endless Summer Vacation album, so Cyrus, of course, wore head-to-toe Gucci.
2023: Versace Show
Attending Versace’s fall 2023 fashion in West Hollywood, Cyrus of course showed up in this Atelier Versace gown with a bit of a split personality.
2022: Miley’s New Years Eve Party
Not a red carpet, but still an absolute serve, Cyrus wore a Versace spring/summer 2005 pink halter dress to perform at her New Years Eve special. It was just one of the many vintage looks she wore for the event.
2022: NBC Upfront
Attending and performing at the NBC Upfront presentation at New York City’s Radio City Music Hall, Cyrus dug into the archive for this Dior gown designed during John Galliano’s days as creative director.
2020: MTV Video Music Awards
Cyrus wore a sheer, black dress covered in mirror details from Mugler fall 2020 to the MTV VMAs.
2019: Camp: Notes on Fashion Met Gala
The singer embraced an ‘80s aesthetic in a black and emerald striped Saint Laurent geometric mini dress at the Met Gala in 2019, an event she attended with her then-husand, Liam Hemsworth.
2019: Avengers: Endgame Premiere
Considering she was attending the premiere of her brother-in-law’s movie, it makes sense that Cyrus kept things lowkey in a black Saint Laurent column dress with a keyhole cutout.
2019: Vanity Fair Oscar Party
The plunging neckline of this black sequin Saint Laurent dress provided the perfect frame for Cyrus’ Bulgari Serpenti necklace.
2019: Isn’t It Romantic Premiere
While one would never describe Cyrus’ style as “romantic,” she embraced the film’s theme and wore this gorgeous, sheer ruffled Valentino pre-fall 2019 gown to the Isn’t It Romantic premiere in 2019.
2019: Grammy Awards
While Cyrus has worn some pretty wild things to red carpets in the past, she kept it sleek and simple at the Grammys in 2019, wearing a Mugler suit with a contoured jacket and cropped pants.
2018: Heavenly Bodies: Fashion & The Catholic Imagination Met Gala
Cryus wore a black Stella McCartney dress with a deep plunge in both the back and in the front.
2018: Vanity Fair Oscar Party
The singer wore a two-toned satin Prabal Gurung pre-fall 2018 dress to the Vanity Fair Oscar party.
2018: Elton John AIDS Foundation’s Academy Awards Viewing Party
Earlier in the evening, she went for a much more shocking look, wearing a bright pink and silver sequin-covered Moschino fall 2018 dress to Elton John’s annual viewing party, which she attended with her then-fiancé, Hemsworth.
2018: Grammy Awards
Cyrus accessorized her Jean-Paul Gaultier fall 2007 couture jumpsuit with a white rose to show her support for the Time’s Up movement.
2017: Thor: Ragnarok Premiere
Liam Hemsworth and Cyrus loved to make date nights out of Chris Hemsworth’s various Marvel premieres. At this one in 2017, Liam kept things casual in a black suit with white sneakers while Cyrus brought the color in a floral ‘60s-inspired Maria Escote dress.
2015: MTV Video Music Awards
When Cryus hosted the MTV VMAs in 2015, she brought out a whole lot of unique looks, but she began the night in this silver bondage-inspired, crystal-covered Versace ensemble.
2015: China: Through the Looking Glass Met Gala
Cyrus wore an Alexander Wang fall 2015 dress with exaggerated cutouts to the Met Gala in 2015.
2015: Grammy Awards
The singer loves some unexpected cutouts on a dress, which is likely why she was drawn to this Alexandre Vauthier spring 2015 couture look for the Grammys.
2015: W’s Shooting Stars Exhibit Opening
When it comes to dressing, Cyrus is often inspired by different decades, and this Balmain spring 2015 jumpsuit is definitely evoking the ‘70s.
2014: MTV Video Music Awards
Cyrus kept it simple at the MTV VMAs in 2014, wearing a black leather two piece set from the Alexandre Vauthier fall 2014 couture collection.
2013: American Music Awards
While Cyrus loves nothing more than a wild, skin-barring look, sometimes she likes to mix things up and keep things simple, like she did when she wore this white Versace suit to the AMAs in 2013.
2013: MTV Europe Music Awards
Cryus paid homage to the late rappers Biggie Smalls and Tupac Shakur in a NY Vintage dress fashioned from a graphic tee.
2013: MTV Video Music Awards
The singer paired her embellished Dolce & Gabbana set with her signature space buns at the VMAs in 2013
2013: PUNK: Chaos to Couture Met Gala
Cyrus looked as cool as ever in a mesh Marc Jacobs dress at the Met Gala in 2013.
2012: Billboard Music Awards
The singer paired a Friends-inspired Rachel hairdo with a Jean Paul Gaultier white double-breasted jacket and mini dress.
2012: The Hunger Games Premiere
Cyrus supported her then-boyfriend, Hemsworth, at the premiere of his film while wearing a black embroidered Emilio Pucci spring 2012 bustier and skirt set.
2012: Vanity Fair Oscar Party
The singer embraced old Hollywood style and wore a gray, long sleeved Roberto Cavalli gown with a chiffon skirt to the Vanity Fair Oscar party in 2012.
2011: MTV Video Music Awards
Wearing a gray, printed Roberto Cavalli dress, Cyrus attended the VMAs in 2011.
2011: Nickelodeon Kids’ Choice Awards
Cyrus went for a more bohemian vibe at the Kids’ Choice Awards in 2011, opting to wear a floral Dolce & Gabbana dress with long, layered necklaces.
2011: Grammy Awards
Wearing a sequin-covered animal print Roberto Cavalli gown, Cyrus attended the Grammys in 2011.
2010: MTV Europe Music Awards
Cyrus went for a preppier look at the 2010 EMAs, opting to wear a tiered halter dress with a bow detail from Dolce & Gabbana.
2010: The Last Song Premiere
Hemsworth and Cyrus attended their first red carpet together in 2010 for the premiere of their film, The Last Song. For the big event, Cyrus wore a black leather one-shoulder knee-length dress from Thomas Wylde while Hemsworth added some color with a blue jacket.
2010: Academy Awards
Cyrus added a bit of edge to her champagne-colored Jenny Packham dress with the help of some dark eye makeup.
2010: Grammy Awards
Keeping things a bit more casual, Cyrus attended the Grammys in 2010 wearing a denim Hervé Léger by Max Azria spring 2010 bandage dress.
2009: Hannah Montana: The Movie Paris Premiere
Cyrus went for a girlier look for the Paris premiere of her film, opting for a high neck, black and white Dolce & Gabbana dress covered in butterflies.
2009: Hannah Montana: The Movie UK Premiere
At the UK premiere, she went with a silver Hervé Léger by Max Azria mini dress with padded shoulders.
2009: Academy Awards
Cyrus looked all grown up when she attended the Oscars wearing this embellished, scalloped Zuhair Murhad gown seemingly inspired by Christian Dior’s Junon dress.
2009: Golden Globe Awards
The singer looked like a Grecian goddess in this strapless, gold and white Marchesa gown with a sheer overlay.
2008: American Music Awards
Cyrus also wore Marchesa to the AMAs in 2008, this time in the form of a black and gold mini dress.
2008: Academy Awards
Wearing a red Valentino gown, Cyrus attended her first Oscars in 2008.
2008: Grammy Awards
For her first Grammys, Cyrus opted for a silver and white mini dress with her hair dyed black.
2007: Teen Choice Awards
Though Cyrus’ light blue, sequin-covered dress at the 2007 TCAs was absolutely adorable, the singer wasn’t really a fan of it. “It’s very uncomfortable, actually,” she said, according to The Hollywood Reporter. “Every time I move I get, like, stabbed with sequins.”
2007: High School Musical 2 Premiere
Cyrus wore a classic early aughts hot pink mini dress with a sequin-covered bodice and a tight tube skirt to the premiere of the second High School Musical movie in 2007.
2006: CMA Awards
Wearing a colorful, mermaid-style gown, Cyrus attended the CMAs in 2006.
2006: Teen Choice Awards
Cyrus paired jeans with a blue and red polka dotted mini dress for the TCAs in 2006.