Miley Cyrus has been a permanent fixture in pop culture for two decades now. Ever since she starred as the teen idol Hannah Montana on Disney Channel way back in 2006, we have watched her grow into multiple versions of herself. She has been a teen pop star in a blonde wig, a singer swinging on a wrecking ball, the ultimate party girl, a rock star, and an independent woman who can buy herself flowers.
And she’s not going any time soon. Cyrus released her ninth album Something Beautiful earlier this year, and it has been nominated for Best Pop Vocal Album at the 2026 Grammys. But whichever version you know her as, you know Cyrus was proud and unashamed in it.
That rings true for Cyrus’s fashion choices as well. During her time as one of Disney’s brightest starlets, her wardrobe was filled with bright colours, whimsical patterns and skinny jeans that were synonymous with the Y2K era. But as Cyrus grew out of the Hannah Montana persona, she stripped her “good girl” image by getting a pixie cut, bleaching her hair and wearing revealing outfits. Now in her 30s, Cyrus is prioritising style over shock, often stepping out in classic but sleek dresses from Saint Laurent to Versace. As a true chameleon in anything she does, the only constant in Cyrus’s fashion is her boldness and willingness to push boundaries.
Miley Cyrus at the 41st Annual Academy of Country Music Awards
May 23, 2006 attends the 41st Annual Academy of Country Music Awards
Photo: Jeff Kravitz/FilmMagic, Inc
At just 14 years old, Cyrus already knew how to stop a red carpet. At the 2006 ACM Awards, she stepped out in a lilac dress with floral patterns and crystal embellishments, paired with metallic silver sandals. It might not be the most memorable look in her 20-year-long career, but it was peak Y2K, and the best fashion that era had to offer. And doesn’t she just look adorable here?
Miley Cyrus in Marc Jacobs
May 6, 2013 attends the Met Gala celebrating "PUNK: Chaos to Couture" wearing Marc Jacobs
Photo: Larry Busacca/Getty Images
Cyrus said goodbye to Disney by throwing Hannah Montana out the window, and welcomed a more shocking, edgier look. At the 2013 Met Gala, Cyrus turned heads with a black mesh gown from Marc Jacobs with a nude undergarment. Given that 2013’s theme was “PUNK: Chaos to Couture”, Cyrus upped the antics by styling her new bleached pixie cut into spikes.
Miley Cyrus in Saint Laurent
May 6, 2019 attends the Met Gala celebrating "Camp: Notes on Fashion" wearing Saint Laurent
Photo: Kevin Tachman/MG19/Getty Images for The Met Museum/Vogue
A lot happened to Cyrus in 2019. She became quite notable for covering everyone from Ariana Grande to Dolly Parton, and received praise for her performance in a Black Mirror episode. But she also announced her split from her then-husband, Liam Hemsworth. But if there’s anything to look back on for Cyrus in 2019, it’s her immaculate streak in fashion. Most recognisable is her look at the Met Gala. She wore a black-and-green-striped mini dress by Saint Laurent that looked like Christmas wrapping paper. A bit early for the Christmas energy, but who can complain?
Miley Cyrus in Bob Mackie
February 4, 2024 performs "Flowers" at the 66th Grammy Awards wearing Bob Mackie
Photo: John Shearer/Getty Images for The Recording Academy
Started to cry, then remembered… Miley Cyrus finally has a Grammy! At the 2024 awards, her hit song “Flowers” won Best Pop Solo Performance and Record of the Year, earning Cyrus her first (and second!) Grammys. She had five costume changes for the entire night, but the most fabulous was the vintage Bob Mackie dress from 2002 that she performed in. The silver fringes and jewels on the dress sparkled as Cyrus wowed the crowd with one of the most memorable performances of the night.
Miley Cyrus in Alaïa
February 2, 2025 presenting at the Grammys wearing Alaïa
Photo: Kevin Mazur/Getty Images for The Recording Academy
As a pop culture icon in her 30s, Cyrus now knows that sometimes, less is more. She returned to the Grammys in 2025 to present the award for Record of the Year in a black, floor-length Alaïa gown. With the deep neckline on the dress and her dirty blonde hair, no one could take their eyes off Cyrus. Elegant and classic dresses like this one shows just how far Cyrus has come.
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Lead image: Kevin Mazur/Getty Images for The Recording Academy
