Miley Cyrus's Style Transformation Documented in 42 Fascinating Outfits

Miley Cyrus isn't your typical fashion icon. Best known for her extraordinarily avant-garde on-stage ensembles, as well as her often risqué streetwear, she's certainly not afraid to make a statement via her clothing. That said, there are many facets to the singer's style: She has morphed from a cowboy boot–clad tween to L.A. renegade with a weak spot for bra tops and hot pants to an elegant Vivienne Westwood–wearing newlywed. Indeed, the child star turned international sensation turned outspoken feminist surprised even us with her chic wedding attire. And since her big day back in December 2018, we've found ourselves becoming increasingly obsessed with her more grown-up fashion sense.

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The theatrics we've come to expect still remain, but they've been softened; what has really changed is the execution. Her reliance on shock-factor hemlines and nipple pasties has waned—instead, she opts for interesting silhouettes, precision cutouts and sharp separates to make her mark. Sequins will always be an integral part of Miley's style, but where you would have found her in just a sparkly leotard, she'll now wear shiny trousers and a plain top with oodles of jewellery—like the Glastonbury 2019 look above, which we all found ourselves appreciating.

Keep scrolling to see just how much Miley Cyrus's style has changes over the years and we're sure you too will soon be living vicariously through her outfits. 

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The star wore a pair of sleek tailored trousers, an ornate Aladdin-style embroidered waistcoat and Chanel jewels we'd give our right arm to own for a dinner date in London in June 2019.

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Looking like an incredibly chic biker chick at the Saint Laurent menswear show in Malibu in June 2019. 

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Embracing 2019's Met Gala theme—camp—in Saint Laurent emerald sequins and sheer black tights.

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Attending the world premiere of Avengers: Endgame in April 2019 wearing a cutout velvet dress from her go-to brand, Saint Laurent. 

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Kicking back at cinema screening hosted by Miu Miu. We can't get enough of her logo glitter kicks.

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Wearing a pink-lapelled suit from Tom Ford's autumn/winter 2019 collection to the the Women's Cancer Research Fund's charity gala in L.A. in February 2019.

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Miley looked incredible in jet-black, flora-length Saint Laurent sequins as she attended Vanity Fair's annual Oscars after-party in February 2019. 

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Naturally, bouclé served as the dress-code for Charles Finch and Chanel's annual Pre-Oscar Awards Dinner in L.A. in 2019. That hair clip = accessory goals.

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Representing her husband Liam Hemsworth in his absence at the premiere of his new film, Isn't It Romantic, Miley looked next-level glamorous in Maison Valentino crimson tulle. 

Related: Gwyneth Paltrow Just Revisited the Outfit She First Wore 22 Years Ago

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Opting for a sophisticated tuxedo sans shirt or blouse at the 2019 Grammys. 

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For her wedding to Liam Hemsworth in December 2018, Miley looked gorgeous in a Vivienne Westwood satin gown, complete with minimal makeup and effortlessly tousled hair. The epitome of a cool bride. 

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Keeping things casual in bleached skinny jeans, a printed roll-neck and ecru boots for an outing in NYC. 

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Miley's getup is so unexpectedly good, we're considering investing in a faux-fur bucket hat and tartan suit for ourselves. 

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Miley means business as she pairs a blouson-sleeve top with a pair of sleek cigarette trousers and metallic pumps ahead of an interview in December 2018 in New York City. 

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Miley nods to her playful fashion side in green snake print, yellow corsetry and pastel velvet for an outing in London in November 2018. 

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Miley channels Old Hollywood glamour at Vanity Fair's Oscars after-party in February 2018 in this contrasting silk gown from Prabal Gurung.

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Loaning her support to the #MeToo movement by accessorising her 2018 Grammys attire with a white rose, the organisation's iconic emblem.

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For the Grammys 2018 red carpet, only a layered Jean Paul Gaultier tulle creation will do. 

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Opting for Jessica Rabbit's trademark silhouette in a golden, figure-hugging gown as she fulfils her role as a judge and coach on the season finale of The Voice in 2017. 

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The milkmaid-style top feels so right for now, but Miley was ahead of the curve when she wore it back in 2017.

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Making an appearance on Jimmy Fallon in this embellished dress with chic Mandarin collar and sparkle motif. 

Related: All of Cat Deeley's Best Looks From 1999 to, Literally, Last Month

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Unleashing her rock 'n' roll side in chainmail trousers and a vintage band tee.

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Giving Dorothy a run for her money, Miley puts our gingham obsession to shame with this head-to-toe outfit. 

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Crochet is big news this season, but Miley was wearing it long ago (okay—in 2016) with some puppy-print trousers.

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Clashing her prints without a care in whilst out and about in Manhattan in May 2016. Anyone else getting Lily Allen vibes?

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Miley Cyrus made double buns a thing back in 2015. The knee-high socks, however, didn't receive the same pick-up. 

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Taking style cues from Elle Woods in this pink sequin–and-rhinestone co-ord, which she wore to the RED charity event in December 2015. 

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Looking, quite literally, as pretty as a flower as she arrives at Hilarity for Charity's fourth annual variety show in October 2015.

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Wearing her heart on everything but her sleeve to the 2015 amfAR Inspiration Gala New York. This Moschino outfit will forever be one of her most iconic. 

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The cutouts on this Alexander Wang would be daunting to most, but not Miley, who paired it with slick blue hair for 2015's Met Gala. 

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Neon and tartan were the order of the day for the 30th annual Rock and Roll Hall of Fame Induction Ceremony in 2015.

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Looking like a real-life mermaid in aquamarine Marc Jacobs for a charity event in 2013. 

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A tame look during her 2013 sartorial wild streak, we're not sure if we'll be copying Miley's ripped white jeans–and–nipple pasty look anytime soon, but we certainly appreciate the throwback. 

Related: 30 Zoë Kravitz Outfits That Are Worth Looking Back At

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Proving leather and denim will always serve you well in 2013. Quiffs—not so much. 

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Paying homage to her Disney heritage in a look pulled straight from the Marc Jacobs runway. 

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Seeing out 2012 with bleach-blonde hair and body-con cutouts, much like the rest of us did. 

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For the premiere of The Hunger Games in 2012, Miley switched up her style with this boho two-piece. 

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Looking fresh-faced in a sheer panel dress for the People's Choice Awards in January 2012. 

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Floral spaghetti-strap dresses and tousled, waist-grazing hair were practically uniform at the Nickelodeon Kids' Choice Awards in 2011.

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In 2010 at the tender age of 17, Miley chose this princess-worthy gown from Jenny Packham for her first Oscars appearance. 

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Even Miley couldn't resist the allure of the draped minidress circa 2008. 

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At just 15, Miley Cyrus started to become a firm fixture on the event scene. Here she is as a VIP guest to an event in New York City in 2007, where she chose jeans tucked into suede boots, a crop top and layered necklaces—aka everything important in the noughties.

Now that you're suitably obsessed with Miley's style, take a look at another young star whose teenage style is putting us to shame

Opening Image: Getty

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Maxine Eggenberger
Deputy Editor

Maxine Eggenberger is Who What Wear UK’s deputy editor and has over thirteen years of experience in fashion journalism. She been creating engaging and elevated style content specifically for Who What Wear UK since 2018, covering runway reports, emerging trends, long-form features, self-styled shopping stories and columns, including her edit of the best new-in buys. She ensures the highest editorial standards are met across the site, leads the editorial team in their SEO strategy and keyword planning, works closely with the beauty team on content initiatives, represents the brand at industry events, and regularly contributes to social media, including her own Who What Wear UK TikTok franchise, French Style Fridays. Previously, Maxine appeared on ITV's This Morning in her own fashion segment and has interviewed countless celebrities—everyone from Victoria Beckham to Oscar winner Lupita Nyong’o.

Prior to Who What Wear UK, Maxine’s career began when, after completing her first-ever internship at Look magazine, she was offered a position on the brand's fashion desk. She accepted, leaving university a year early in the process. Her passion and natural talent for writing and styling meant she swiftly rose through the ranks to become the title's fashion news and commercial content editor, with a stint as InStyle.co.uk’s fashion and beauty writer along the way. She later served as Look’s acting Editor in Chief, overseeing both print and digital, before embarking on a successful freelance career, working with Grazia, The Pool, and Marie Claire amongst others.

Maxine is based remotely from her countryside home near Edinburgh where she spends her downtime renovating her house, walking her dogs, hosting friends and trying to master the art of making Old Fashioned cocktails.