Miley Cyrus is a style chameleon, constantly reinventing herself both in music and in fashion. From her early days as wholesome pop sensation Hannah Montana, when her wardrobe consisted of rhinestones, sequins and cowboy boots, to her current status as a daring style rockstar in archival Versace, Cyrus’s sartorial choices tell the story of her transformation.
It is safe to say that in this journey, it’s more than just about the clothes. Her style reflects her personal growth, her artistic experimentation, and an unapologetic mantra of “just be yourself.” Here, we take a closer look at the standout moments of the Miley Cyrus style journey, charting her rise from teenage pop ingenue to a global superstar with a wardrobe to match.
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Disney Sweetheart
Billy Ray Cyrus and Miley Cyrus onstage at the 2006 American Music Awards (Photo: Ethan Miller/Getty Images)
As Hannah Montana, Cyrus embodied the quintessential country-pop princess aesthetic with thin scarves, skinny jeans and rhinestones. However, as Miley Cyrus, Disney Channel’s ultimate “it-girl” of the 2000s, she looked every bit of the teen celebrity with wholesome, sparkly dresses.
Can’t Be Tamed
Miley Cyrus performs on stage at the Rock in Rio Madrid music festival (Photo: Getty Images)
With her first major image shift, Cyrus embraced edgier looks, including leather jackets, sheer fabrics, and dark makeup that hinted at her desire to break away from her Disney Channel-curated image.
The Bangerz Phase
Miley Cyrus attends the 2013 MTV Video Music Awards (Photo: Getty Images)
Cyrus shocked and provoked during this era, which included latex bikinis, crop tops, and headline-making moments like her 2013 VMAs appearance in a nude-coloured, two-piece set. Daring choices and misogynistic lyrics aside, her performance with Robin Thicke solidified her place as a pop culture disruptor.
Malibu Moment
Miley Cyrus carries a basket of flowers during the One Love Manchester concert (Photo: Matthew McNulty/Getty Images)
Cyrus went the total opposite direction to her Bangerz look with a much softer, Bohemian style. Around the time of her Younger Now album cycle, she embraced flowy silhouettes and light tones, reflecting a more romantic and grounded outlook.
Plastic Hearts
Miley Cyrus performs at the 2019 Glastonbury Festival (Photo: Harry Durrant/Getty Images)
As she leaned into her rock roots, albeit with a more ‘adult’ edge, Cyrus adopted leather pants, ‘wet look’ hairstyles and glam-rock ensembled, often drawing comparisons to Seventies and Eighties rock icons like Joan Jett.
Couture Queen
Miley Cyrus walks the runway at the Marc Jacobs Ready to Wear Fall/Winter 2020-2021 fashion show (Photo: Peter White/FilmMagic via Getty Images)
Cyrus made bold yet feminine statements with sleek and tailored silhouettes, often incorporating romantic elements like diamond jewellery and elbow-length gloves. She is seen here walking the runway of the Marc Jacobs Autumn/Winter 2020-2021 fashion show.
From the Archives
Miley Cyrus performs onstage during the 66th Grammy Awards (Photo: Amy Sussman/Getty Images)
Cyrus’s recent appearances showcase her growth as an evolving style phenomenon, often coveting rare archival pieces from brands like Versace. At the 2024 Grammy Awards, for example, Cyrus wore a silver beaded Bob Mackie dress from a 2002 collection.
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