From a fresh, young Disney star to a headline-making industry giant, outspoken activist and celebrated humanitarian, Miley Cyrus has already lived one rollercoaster of a life at just 28 years old. Love her or hate her style-wise, you have to respect her passion for a cause, and her willingness to take risks — on the red carpet, and in life. Having just dropped her latest album, Plastic Hearts, it seems like the perfect time for a style evolution like no other for the one-and-only, Miley Cyrus.

Getty Images
1 / 20
Miley Cyrus cements “teen idol” status as Hannah Montana in 2006
Though she’d appeared in smaller roles before landing the lead in Disney’s television series Hannah Montana, it was this part that would turn Miley Cyrus into an overnight sensation, with the show debuting to Disney Channel’s largest audience ever. Quirky, youthful and fun, Miley’s style sense at this point definitely mirrored that of her on-screen character.
In a recent article for Rolling Stone, Miley Cyrus reflected on her tenure as Disney sensation Hannah Montana, and duality of her role on-screen and off-screen during that time: “Really, Hannah Montana was not a character. That wasn’t what the show is about… Everything was always in me. The concept of the show, it’s me. I’ve had to really come to terms with that and not be third-person about it.”
In a recent article for Rolling Stone, Miley Cyrus reflected on her tenure as Disney sensation Hannah Montana, and duality of her role on-screen and off-screen during that time: “Really, Hannah Montana was not a character. That wasn’t what the show is about… Everything was always in me. The concept of the show, it’s me. I’ve had to really come to terms with that and not be third-person about it.”
See also: JLo’s style evolution.

Getty Images
2 / 20
Miley Cyrus is one of the “Hot Hollywood” elite in 2007
Looking slightly more grown up in a black mini dress and Mary-Jane style pumps, Miley Cyrus was all smiles on the blue carpet for US Weekly’s “Hot Hollywood” party in 2007.

Getty Images
3 / 20
Miley Cyrus is all sequins and smiles at the American Music Awards in 2008
Rocking a black-and-gold sequin mini dress and matching pumps, Miley Cyrus seemed to be maturing in her style choices, but still keeping her signature edge.
See also: Beyonce’s style evolution.

Getty Images
4 / 20
Miley Cyrus goes full glam for the Academy Awards in 2009
Looking drop-dead-gorgeous in a sparkly Zuhair Murad gown with tiered skirt and belted waist, Miley Cyrus looked every bit the rising star – and for good reason. With her 2009 musical release of “The Climb” topping the charts, a 16-year old Miley now held the title of the youngest artist ever to have four number-one albums on the Billboard 200 chart.
See also: Jennifer Aniston style evolution.

Getty Images
5 / 20
Miley Cyrus ties one on at the MTV Europe Music Awards in 2010
Miley Cyrus looked sweet and stylish at the 2010 MTV Europe Music Awards, wearing a long, tiered white sleeveless dress with black neck-tie and belt details. The look was a departure from her usual style choices, and signalled a desire to experiment and broaden her fashion identity. This would also be the year that Miley would star in her film The Last Song, opposite Liam Hemsworth – who she dated on-again, off-again during filming the previous year – and who she would go on to marry in 2018 (though the pair would separate in 2019). Her film and fashion choices during this time clearly reflected Miley’s yearning for a more mature image in the industry.

Getty Images
6 / 20
Miley Cyrus keeps it edgy at the MTV Video Music Awards in 2011
Wearing her hair slicked back and rocking an edgy long-sleeved print gown, Miley Cyrus was definitely on track for a major shift in her look at the MTV Video Music Awards in 2011. Looking cool and confident, Miley seemed to easing into a style that was all her own.
See also: Christina Ricci style evolution.

Getty Images
7 / 20
Miley Cyrus nails it in full glam at the Vanity Fair Oscar party in 2012
2012 was a year of major style changes for Miley Cyrus. Taking the red carpet by storm alongside Liam Hemsworth as her plus one, Miley wore a silver long-sleeved Roberto Cavalli gown, with her signature long locks chopped above the shoulder and styled with old Hollywood waves. The look was mature, sleek and an unexpectedly conservative choice for the usually-edgy artist.

Getty Images
8 / 20
Miley Cyrus keeps it short and sweet at the Australians in Film Awards and Benefit Dinner in 2012
No doubt bias toward her own Australian, then-boyfriend Liam Hemsworth, Miley Cyrus stepped out and stole the show in a black mini dress with cut-out details. Wearing her shorter locks in a sleek, straight style, and a minimal beauty look, Miley definitely nailed this look.
See also: Mariah Carey style evolution.

Getty Images
9 / 20
Miley Cyrus 2.0 takes the red carpet at the MTV Video Music Awards in 2012
One of the most drastic style shifts Miley Cyrus made in 2012 was her hair. From the above-shoulder, red locks she sported for the first half of the year to this look: a platinum blonde Mohawk style. While the look was a major change from the signature red hair we’d gotten used to seeing on the star over the years, the platinum blonde just worked. Confidently sporting the new style with a super low-cut black gown to the MTV Video Music Awards in 2012, Miley looked more comfortable than ever in front of the cameras. The former Disney star seemed to finally be coming into her own.

Getty Images
10 / 20
Miley Cyrus is punk personified at the MET Gala in 2013
With the theme being “PUNK: Chaos to Culture”, the 2013 MET Gala left themselves open to some pretty outrageous punk-inspired fashion. One of the most-talked about looks of the evening? Miley Cyrus. Rocking a black, floor-length, long-sleeved, mesh gown and short, spiky, platinum-blonde hair, Miley nailed the theme – and gave fans a glimpse into the style that would soon become her everyday look.
See also: Rihanna style evolution.

Getty Images
11 / 20
Miley Cyrus sticks her tongue out — and won’t stop — backstage at the MTV Video Music Awards in 2013
For the 2013 MTV Video Music Awards, Miley Cyrus held nothing back and showcased a full range of barely-there costume choices throughout the evening. While we loved her gutsy choices and commitment to doing her thing, we could have done with a little less of that tongue-out pose. This evening seemed to signal the rise of a new, no F’s given Miley – and fans seemed unsure of whether this signalled a shift in confidence – or a cry for help.
While her outfit choices might have taken center stage that evening, it would be Miley Cyrus’ borderline x-rated performance on-stage with Robin Thicke that would make headlines the next day. Between his Beetlejuice-inspired suit and her foam finger, we’re still at a loss…
While her outfit choices might have taken center stage that evening, it would be Miley Cyrus’ borderline x-rated performance on-stage with Robin Thicke that would make headlines the next day. Between his Beetlejuice-inspired suit and her foam finger, we’re still at a loss…

Getty Images
12 / 20
Miley Cyrus x Moschino is pretty in pink in 2014
Rocking a pink bra and mesh skirt and jacket outfit by Moschino, complete with sequin heart-shaped glasses and pink hair, Miley Cyrus turned up (and of course, stuck her tongue out) in support of longtime friend and designer Jeremy Scott in Miami in 2014.

Getty Images
13 / 20
Miley Cyrus miraculously avoids a wardrobe malfunction at an amfAR event in 2014
Wearing a black dress with a seriously risqué bondage-style top, Miley Cyrus stepped out — but somehow kept it all tucked in — for the amfAR LA Inspiration Gala in 2014.
Fashion aside, Miley Cyrus is no stranger to philanthropic events and causes. Founded in 2014, Miley spearheaded the Happy Hippie Foundation, aimed at supporting the LGBTIQ+ young community, eventually expanding this foundations’ platform to also support animal welfare – amongst several other causes the star champions.

Getty Images
14 / 20
Miley Cyrus (almost) bares it all while hosting the MTV Video Music Awards in 2015
Fully-immersed in her wild-Miley phase, Miley Cyrus hosted the 2015 MTV Video Music Awards and kicked off the evening by stepping out in a custom, silver harness-detail Versace outfit and boots. Styled by Simone Harouche, the star set the tone for the evening’s costume choices in this outfit, which had her nearly-naked except for some strategically-placed silver harnesses and jewelled-mesh skirting.
See also: Selena Gomez style evolution.

Getty Images
15 / 20
Miley Cyrus disappoints at a film screening in 2016
Of all the ways to describe Miley Cyrus’ style choices over the years, this is the first time “boring” came to mind. While the photography-graphic print in her jumpsuit had a cool feel, the overall cut of the design on the petite star, even with the belted detail, totally missed the mark. The result was a boxy shape and overwhelming amount of fabric, that completely drowned out the otherwise beautiful Miley.

Getty Images
16 / 20
Miley Cyrus knows how to stay on theme at iHeartRadio Music Festival in 2017
If there’s one thing Miley Cyrus can get on board with, it’s a costume theme. For the 2017 iHeartRadio Music Festival, Miley wore her heart on her sleeve – and embellished everywhere else on her sheer, two-piece outfit, complete with heart-detail accessories and red panties.
See also: Kristen Stewart’s style evolution.

Getty Images
17 / 20
Miley Cyrus stuns at the Vanity Fair Oscar party in 2018
Wearing a black-and-white pre-fall gown by Prabal Gurung, Miley Cyrus had all eyes on her at the Vanity Fair Oscar party in 2018.

Getty Images
18 / 20
Miley Cyrus sets a new standard for off-duty style – with a message – while in New York in 2018
Spotted in New Jersey in 2018, it’s impossible not to love Miley Cyrus in her funky oversized plaid suit and faux fur hat. The icing on the cake? Miley’s cropped white tee, which reads “protect kids, not guns”.
See also: Winona Ryder style evolution.

Getty Images
19 / 20
Miley Cyrus serves up sequin glam at the Vanity Fair Oscar party in 2019
Wearing a black sequin gown by Saint Laurent, featuring a lower-than-low neckline, Miley Cyrus knocked it out of the park at the 2019 Vanity Fair Oscar party.

Getty Images
20 / 20
Miley Cyrus stuns in Tom Ford in 2020
For the most part, her twerking days are done, but that edgy vibe still remains. The singer is currently rocking a mullet but perhaps it can no longer be contained and is being grown out into something more conventional. Pfft, nah! This is Miley we're talking about. She might come out of isolation with a shaved head — and no one would be surprised.
See also: Mindy Kaling style evolution.
ADVERTISEMENT
ADVERTISEMENT
ADVERTISEMENT
ADVERTISEMENT
ADVERTISEMENT
ADVERTISEMENT