Miley Cyrus All-Time Best and Worst Fashion Moments
A total transformation! Miley Cyrus has had quite the dramatic style transformation since she stepped into the spotlight with her 2006 hit show Hannah Montana.
Because while she may have started out in sweet dresses and cowboy boots that took inspiration from her country roots, she made it clear in the years that followed that she’s not afraid to shy away from shock value when it comes to her style.
In a behind-the-scenes video with ScreenSlam in August 2016, she revealed that her skin-baring on-stage looks and out-of-the-box fashion statements are actually a form of distraction.
“The way I dress to distract — it’s a comforting thing to me,” she said. “I think style can be something that can make you feel comfortable. It’s something to kind of not maybe just have everyone staring into you should. That’s [fashion] is giving them something to look at.”
While the “Party in the USA” singer has taught Us to always be prepared for a style surprise (think: her Simone Harouche bubble dress at the 2015 MTV Video Music Awards), she’s also fully equipped at rocking a gorgeous gown or sophisticated suit.
Because according to a 2021 interview she did with Vogue, Cyrus’ wide-ranging style is pretty reflective of her personality at any point in time.
“Fashion to me is kind of like flipping yourself inside out. It’s like wearing your heart, wearing your guts, wearing your values, wearing your identity, wearing your pain, wearing you joy,” she revealed. “There’s something kind of childlike about it. You’re so fearless when you get yourself dressed when you’re a kid. You don’t think about what someone will think of you or what they’ll judge.”
She added: “It’s just about expression and how you feel that day. There’s a fearlessness. And so when I get dressed, I try to kind of think like my inner child and be genuine and authentic in whatever I’m wearing.”
From uber-girly ensembles like her maroon, princess-esque Zac Posen tulle gown at the 2018 Grammys to her bondage-inspired leather look at the 2019 iHeartRadio Music Festival, Cyrus definitely doesn’t stick to any particular aesthetic.
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So without further adieu, keep scrolling to see how the “Slide Away” singer’s style has evolved from her Disney channel days to her present-day edge following the release of her album Endless Summer Vacation in March 2023.
Us Weekly’s Stylish is rounding up her most memorable looks of all time, ahead!
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