Miley Cyrus is a red carpet chameleon that always leave’s us guessing what she’ll wear next. Ahead, we look back at 20 of her most transformative looks.

This style chameleon always keeps us guessing.

Just like her on-screen alter ego once sang, when it comes to her sense of style, Miley Cyrus is all about having “the best of both worlds.” Equally talked-about for her unique aesthetic when she’s off-duty as the looks and outfits she chooses for the red carpet and the stage, this chart-topper has been influencing how her followers get dressed since she was just a tween. 

From the moment she entered the spotlight during her Disney channel heyday, Cyrus has gone through no shortage of fashion iterations—from rock princess to provocateur and country music belle to indie icon. But thanks to a long-time collaboration with her award-winning stylist Bradley Kenneth over the last decade, the Tennessee native has transformed into a veritable fashion plate with whom luxury brands are clamoring to work.  

The proof was in the pudding recently at the 2024 Grammys, where Cyrus was the most celebrated artist of the night, having finally received not one but two awards from the Recording Academy. For her milestone career highlight, the star changed outfits at a dizzying pace — rocking a total of five unforgettable outfits. One such look was a vintage Bob Mackie minidress from 2002 worn for her impressive performance, which led to an unforgettable image of an empowered pop star at the top of her game.

This latest chapter in her style journey has also seen her land coveted campaigns with Dolce & Gabbana, Gucci, and Marc Jacobs. Thanks to Cyrus and Kenneth’s inimitable mix of genres, references, and eras, her music videos and album art are dissected by eagle-eyed fans. 

While fans are eagerly camping out to get updates about what the selective star is going to do next, professionally and personally, here’s a look back at some of Miley’s most memorable moments in the style stakes as we await whatever surprise she’ll have in store for us next.

Miley Cyrus in Maison Margiela at the Grammy Awards 2024

It was a look that divided opinion, but Cyrus has never been known to play it safe. For her much-talked-about attendance at this year’s Grammy Awards, the star hit the red carpet in an intricate gold gown made from over 14,000 safety pins—inspired by creative director John Galliano’s Fall ‘97 collection—and mustard yellow Tabi heels. A special mention must be made to her backcombed bouffant, which turned out to be a nod to the late Tina Turner.

Miley Cyrus in Versace at the Fashion Los Angeles Awards in 2023

In her first appearance since the release of her smash hit album Endless Summer Vacation, Cyrus showcased her newly-dyed two-tone brunette and blond hair in a figure-cinching Versace corset and latex skirt. The starlet attended the event to honor her beloved stylist and best friend, Bradley Kenneth, with the nod for Music Stylist of the Year. Deserved!

Miley Cyrus in Gucci x Balenciaga at the LACMA Art+Film Gala in 2021

Wearing a full head-to-toe, off-the-runway number from the Gucci x Balenciaga collaboration is not for the faint-hearted, but Cyrus has the confidence to pull it off with ease. For the LACMA Art+Film Gala, the chanteuse rocked an hourglass logo, floral print blazer, and second-skin legging boots.

Miley Cyrus in Mugler at the MTV Video Music Awards in 2020

Her VMA appearances are guaranteed traffic drivers—and Cyrus’ so-called naked dress in 2020 was no exception. The singer looked, to use one of her favorite phrases, “sickening,” in a sheer black embellished dress from Mugler’s Fall Winter 2020 collection, which she teamed with matching opera-length gloves and a diamond choker necklace for extra drama.

Miley Cyrus in Saint Laurent at the Spring Summer Men’s 2020 show

In a relatively rare fashion week appearance, Cyrus paid homage to her ‘indie sleaze’ and aughts-era rock chick roots by attending the Saint Laurent show in Malibu in ripped black denim and biker boots juxtaposed with a chic Parisian Girl-approved trophy blazer. 

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Miley Cyrus in Valentino at the LA premiere of Isn’t It Romantic in 2019

In a total departure from her typical red carpet appearances over the years, when Cyrus stepped out for the premiere of Isn’t It Romantic on behalf of her then-husband and the movie’s star Liam Hemsworth, who was battling health issues, her sheer and romantic voluminous Valentino gown placed her on best-dressed lists everywhere.

Miley Cyrus in Saint Laurent at the Vanity Fair Oscars After Party in 2019

For the annual A list-studded bash post-Oscars, Cyrus was polished to perfection in a long-sleeved sequin gown with a plunging neckline from Saint Laurent by Anthony Vaccarello. The icing on the cake? Divine diamonds by Bulgari.

Miley Cyrus in Saint Laurent at the Met Gala in 2019

We know she loves a theme! For the star-studded unveiling of the Camp: Notes on Fashion exhibit at the Costume Institute, Cyrus dialed up the quirk factor in a sequin mini that was a slay from all angles. Literally! The Saint Laurent number looked like a retro ‘80s cocktail dress from the front, but from the side, gave the appearance of being a sparkly well-wrapped present.

Miley Cyrus in Tom Ford during NYFW in 2019

The year 2019 proved to be a particularly stylish one for Miley as she increasingly leaned into the more sophisticated and mature side of her 20s. Without ever sacrificing the fashion factor, of course. Case in point: when she pulled up to the Tom Ford show during NYFW in a scene-stealing outfit complete with a thoroughly ‘90s hat that Pamela Anderson would be proud of.

Miley Cyrus in Stella McCartney at the Met Gala in 2018

A simple black dress, but Miley-ified! For the Heavenly Bodies-themed Met Gala in 2018, Cyrus attended the event with Stella McCartney. In her pared-back but sultry custom silk gown, she still looked every inch her insouciant self thanks to sleek jewelry and countless visible tattoos.

Miley Cyrus in Christian Cowan at the iHeart Radio Music Festival in 2017

Giving her fans even more reason to get all heart-eyes-emoji, Cyrus opted for this fun white lace and velvet red heart-emblazoned ensemble from Christian Cowan’s Spring 2018 show. She further upped the ante with fire engine-hued accessories and strappy sandals, not to mention a matching lip.

Miley Cyrus in Moschino at the amfAR Inspiration Gala in 2015

Miley and Moschino are a sartorial match made in heaven. A staunch fan of the label’s then-creative director Jeremy Scott and his tongue-in-cheek creations, in one unforgettable red carpet moment, Cyrus stepped out in a kitschy heart-emblazoned dress with an oversized bow and chunky-sole boots to receive the evening’s honor in recognition of her fight against AIDS.

Miley Cyrus in Alexander Wang at the Met Gala in 2015

For the "China: Through the Looking Glass" exhibit opening night, Cyrus didn’t shy away from showing off her strong physique. The performer opted to wear a studded gown by Chinese-American designer Alexander Wang, which looked oh-so-cool with her wet-look slicked back hair, effortless “no-makeup” makeup, and a punky ear cuff.

Miley Cyrus in Alexandre Vauthier at the MTV VMAs in 2014

In a look that was both sharp yet chic, Cyrus opted for a two-piece structured black leather outfit by Alexandre Vauthier Couture when she stepped out for the MTV VMAs in 2014. The evening’s appearance is made even more memorable, as it was when Cyrus had a homeless youth named Jesse Helt accept her award on her behalf in order to give a rousing speech about the homelessness crisis in LA.

Miley Cyrus in vintage Dolce & Gabbana at the MTV VMAs in 2013

Before she shocked the world with *that* infamous performance later in the evening (one word: twerking), Cyrus hit the red carpet at the MTV VMAs in a vintage jewel-embellished co-ord by Dolce & Gabbana and her soon-to-be-signature double twisted top-knot hairstyle.

Miley Cyrus in Azzaro at the Elton John AIDS Foundation Oscars Party in 2013

In this memorable red carpet outing, Cyrus stripped it back in a white body-con jersey maxi dress by Azzaro, with a sensual low back featuring a chunky chain detail. It also marked a turning point towards a more mature and streamlined side of her personal style and away from her teenage years, particularly when accentuated by eye-catching Lorraine Schwartz diamonds.

Miley Cyrus in Omo by Norma Kamali at the VH1 Divas event in 2012

Officially entering her 20s, Cyrus began to dabble in more daring moments—often changing her hairstyles as much as her fashion. Here, she turned a new page in a peroxide pixie crop, wearing the ‘Alligator’ cut-out dress by Omo by Norma Kamali, Jean-Michel Cazabat shoes, and Lorraine Schwartz jewels.

Miley Cyrus in Roberto Cavalli at the Vanity Fair Oscars party in 2012

On the arm of her then-partner Liam Hemsworth, Cyrus showed yet another hairdo as she donned an embroidered chiffon gown by Roberto Cavalli for back-to-back appearances at the Vanity Fair Oscar party and Elton John Oscar party.

Miley Cyrus in Roberto Cavalli at the Grammy Awards in 2011

Settling into her boho-meets-rock royalty era, Cyrus prowled the red carpet in a tiger-print Roberto Cavalli sequin number at the Grammys.

Miley Cyrus in Jenny Packham at the Academy Awards in 2010

Ah, were we ever so young! Riding high on her Disney channel fame, Cyrus routinely wore princess-style embellished and floaty dresses for notable appearances, such as this champagne bustier and tulle dress from British designer Jenny Packham that she wore to the Oscars in 2010 when she was just 17 years old.