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Just as her on-screen alter ego once sang, when it comes to her sense of style, Miley Cyrus seeks to have “the best of both worlds.” As well known for her unique off-duty aesthetic as she is for the looks and outfits she chooses for the red carpet and stage, this chart-topper has been influencing the way her followers dress since she is just a teenager.
From the time she burst into the spotlight during the heyday of her Disney Channel, Cyrus has had no shortage of fashion iterations, from rock princess to provocateur and country music belle to indie icon. But thanks to a longtime collaboration with her award-winning stylist Bradley Kenneth over the past decade, the Tennessee native has transformed herself into a fashion plate that luxury brands are clamoring to work with.
The proof was recently at the 2024 Grammys, where Cyrus was the most celebrated artist of the night, ultimately receiving not one but two awards from the Recording Academy. For her career milestone, the star changed outfits at a dizzying pace, sporting a total of five unforgettable outfits. One of those looks was a vintage Bob Mackie mini dress from 2002 worn for her impressive performance, which created an unforgettable image of an empowered pop star at the top of her game.
This latest chapter in her style journey also landed her coveted campaigns with Dolce & Gabbana, Gucci and Marc Jacobs. Thanks to Cyrus and Kenneth’s inimitable blend of genres, references and eras, his music videos and album covers are dissected by eagle-eyed fans.
As fans eagerly camp out to get updates on what the selective star is going to do next, professionally. And Personally, here’s a look back at some of Miley’s most memorable style moments while we wait for what surprise she has in store next.
Miley Cyrus in Maison Margiela at the 2024 Grammy Awards
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The look divided opinion, but Cyrus has never been known for playing it safe. For her high-profile appearance at this year’s Grammy Awards, the star hit the red carpet in an intricate gold dress made from more than 14,000 safety pins, inspired by creative director John Galliano’s fall 1997 collection, and Tabi heels mustard yellow. 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
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For his first appearance since the release of his successful album Endless summer vacation, Cyrus showed off her newly dyed two-tone brown and blonde hair in a skin-tight Versace corset and latex skirt. The starlet attended the event to honor her beloved stylist and best friend, Bradley Kenneth, with the nomination for Music Stylist of the Year. Deserved!
Miley Cyrus in Gucci x Balenciaga at the LACMA Art+Film gala in 2021
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Wearing a full head-to-toe, off-the-runway number from the Gucci x Balenciaga collaboration isn’t for the faint-hearted, but Cyrus has the confidence to pull it off with ease. For the LACMA Art+Film Gala, the a singer shaken an hourglass logo, a floral print blazer and second-skin legging boots.
Miley Cyrus in Mugler at the MTV Video Music Awards in 2020
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Her appearances at the VMAs are guaranteed traffic drivers — and Cyrus’ so-called nude dress in 2020 was no exception. The singer looked, to borrow one of her favorite expressions, “sickening” in a sheer black embellished dress from Mugler’s Fall ’20 collection, which she teamed with matching opera-length gloves and to a diamond choker necklace for added drama.
Miley Cyrus in Saint Laurent at the Men’s Spring Summer 2020 show
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In a relatively rare appearance at fashion week, Cyrus paid homage to her “indie sleaze” and chick-rock roots of the era by attending the Saint Laurent show in Malibu in ripped black denim and biker boots juxtaposed with a blazer chic Parisian Girl approved trophy.
Miley Cyrus in Valentino at the Los Angeles premiere of Isn’t It Romantic in 2019
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Unlike 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 film star Liam Hemsworth, who was battling health issues, her voluminous, sheer and romantic Valentino dress landed her on best-dressed lists around the world.
Miley Cyrus in Saint Laurent at the Vanity Fair Oscars after party in 2019
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For the annual post-Oscars bash, Cyrus was polished to perfection in a long-sleeved sequin dress with a plunging neckline from Saint Laurent by Anthony Vaccarello. The icing on the cake? Divine diamonds from Bulgari.
Miley Cyrus in Saint Laurent at the Met Gala in 2019
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We know she loves themes! For the unveiling of the Camp: Notes on Fashion exhibition at the Costume Institute, Cyrus used the weird factor in a sequined mini that was killer from every angle. Literally! The Saint Laurent number looked like a retro ’80s cocktail dress from the front, but from the side it gave the appearance of a well-wrapped sparkly gift.
Miley Cyrus in Tom Ford during NYFW 2019
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2019 proved to be a particularly stylish year for Miley, as she leaned more and more toward the more sophisticated, mature side of her 20s. Without ever sacrificing the fashion factor, of course. Case in point: when she showed up at Tom Ford’s NYFW show in a scene-stealing outfit with a ’90s hat that Pamela Anderson would be proud of.
Miley Cyrus in Stella McCartney at the Met Gala in 2018
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A simple black dress, but Miley-ified! For the Celestial Bodies-themed Met Gala in 2018, Cyrus attended the event with Stella McCartney. In her sleek yet sensual custom silk gown, she still looked carefree thanks to elegant jewelry and countless visible tattoos.
Miley Cyrus as Christian Cowan at the iHeart Radio Music Festival in 2017
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Giving her fans even more reason to have heart-eyed emoji, Cyrus opted for this fun white lace and red velvet ensemble adorned with a heart from Christian Cowan’s Spring 2018 show. She upped the ante again with firefighter-themed accessories and strappy sandals, not to mention a matching lip.
Miley Cyrus in Moschino at the amfAR Inspiration Gala in 2015
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Miley and Moschino are a sartorial match made in heaven. An avid fan of Jeremy Scott, then the brand’s creative director, and his tongue-in-cheek designs, in an unforgettable red carpet moment, Cyrus stepped out in a kitschy heart-adorned dress with an oversized bow and ankle boots. thick sole to receive the prize. evening of honor in recognition of his fight against AIDS.
Miley Cyrus in Alexander Wang at the Met Gala in 2015
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For the opening night of the “China: Through the Looking Glass” exhibition, Cyrus didn’t hesitate to show off her strong physique. The performer chose to wear a studded dress by Chinese-American designer Alexander Wang, who looked so cool with her slicked-back wet hair, effortless “no makeup” makeup, and a punky ear cuff.
Miley Cyrus in Alexandre Vauthier at the MTV VMAs in 2014
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In a look that was both sharp and chic, Cyrus opted for a structured black leather two-piece outfit by Alexandre Vauthier Couture when she stepped out for the MTV VMAs in 2014. Even more memorable was the evening’s appearance, as she was when Cyrus asked a young homeless man named Jesse Helt to accept his award on his behalf in order to give a riveting speech about the homeless crisis in Los Angeles.
Miley Cyrus in vintage Dolce & Gabbana at the MTV VMAs in 2013
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Before shocking the world with *that* infamous performance later in the evening (one word: twerk), Cyrus hit the MTV VMAs red carpet in a vintage bejeweled co-ord by Dolce & Gabbana and her near future. be-signature double twisted top knot hairstyle.
Miley Cyrus in Azzaro at the Elton John AIDS Foundation Oscar Party in 2013
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During this memorable red carpet outing, Cyrus stripped it down in a figure-hugging white jersey maxi dress by Azzaro, featuring a sultry low back adorned with a chunky chain. It also marked a shift toward a more mature, refined side of her personal style and away from her teenage years, especially when accented by eye-catching Lorraine Schwartz diamonds.
Miley Cyrus as Norma Kamali’s Omo at the VH1 Divas event in 2012
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Officially entering her 20s, Cyrus began to venture into more daring moments, often changing her hairstyle as much as her fashion. Here, she turned a new leaf in a peroxide pixie crop, wearing Norma Kamali’s Omo “Alligator” cutout dress, Jean-Michel Cazabat shoes and Lorraine Schwartz jewelry.
Miley Cyrus in Roberto Cavalli at the Vanity Fair Oscars in 2012
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Armed with then-partner Liam Hemsworth, Cyrus showed off yet another hairstyle as she donned an embroidered chiffon gown by Roberto Cavalli for back-to-back appearances at Vanity Fair’s Oscar party and ‘Elton John.
Miley Cyrus in Roberto Cavalli at the 2011 Grammy Awards
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Settling into her days of boho-meets-rock royalty, Cyrus walked the red carpet in a sequined, tiger-print number by Roberto Cavalli at the Grammys.
Miley Cyrus as Jenny Packham at the Oscars in 2010
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Ah, were we so young! Building on her Disney Channel fame, Cyrus regularly wore floral, floaty princess-style dresses for notable appearances, like this champagne bustier and tulle gown by British designer Jenny Packham she wore to the 2010 Oscars while she was only 17 years old. .
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