Hannah Montana To Miley Cyrus: 15 Photos Showcasing The Evolution Of Her Wild Fashion Styles

In March 2006, Miley Cyrus started to star in the Disney Channel’s Hannah Montana, and the show was so successful that it became the highest-rated series on basic cable. Fame followed quickly and Cyrus’ alter ego Hannah Montana became a teen idol among many girls who looked up to her for her wholesome and sweet image, a relatable girl who was growing up onscreen while her fans did the same. She was only 11 at the time, but she was already becoming famous for her outfits that bordered from sweet to tacky, foreshadowing the fashion diva she would become when she turned 16.

Most outfits Cyrus wore were simple—she usually dressed up in kid-style jeans and cute tanks—and she always had on cowboy boots to show off her country roots. During the life of Hanna Montana, Cyrus soon became a rebellious chameleon, wishing to shed that Disney princess image which would later define her years to come, and fans were always curious to watch what she would wear next because of her ever-changing style choices. From 11 to age 20, we take you through the evolution of her wild fashion styles, from glamorous pop singer who looked as if she stepped out of a 1950s movie, to an audience-provoking barely adult who bumped and danced while nearly nude at the VMAs that was so wild, provocative and sexualized that it actually put the word “twerking” in the dictionary.

15 2006 - Demure, Feminine And Innocent - The Hannah Montana Era


2006 marked her fashion transformation, as she started to appear on the red carpet and award shows. But she was not provocative at the time. For the red carpet, she was covered up in a tweed blazer and flared jeans. At a Disney press event, she wore something similar, a suit jacket and jeans. At the Country Music Awards, also in 2006, she accompanied her dad, country singer Billy Ray Cyrus, in a multi-colored mermaid-style gown, the first time she would start dressing up in colored clothes.

She continued to wear cowboy boots, pairing them with sweet mini dresses in different patterns and colors. This was also the time that Miley started wearing glitter clothing, which she showed off at the 41st Annual Academy of Country Music Awards. These looks were sophisticated for a young star, but Cyrus off the carpet was a girl who wore funky vintage outfits.

14 2007 - Sequins And Multi-Colors

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2007 saw Miley’s blond-bangs for her show, and the first time we would see her in sequins. In fact, sequins became a big part of her look in 2007, and she wore them on many outfits. When she performed as Hannah Montana on Good Morning America, she wore a blue sequined shirt that coordinated with her blue boots. Then she was seen wearing a whimsical sequined dress during her first appearance at the Teen Choice Awards ceremony where she won Choice TV Actress and Choice Summer Music Star.

For the VH1 Big in '06 event, also in 2007, she wore a shiny gold sequined top. She changed her look again that year when she started wearing attire with accessories such as buttons and metallic details and color combinations in stripes while also sporting bright-colored shoes.

13 2008 - From Sophisticated To Edgy


At the start of the year, Miley continued wearing her signature go-to look, a dress, mini-skirt, or top topped off with loads of shiny sequins. But the sequin look that year changed from girly-girl to mature, such as when she wore a silver sequined mini dress complete with a silk top and black pumps. She showed a lot of leg at Disney's premiere of "Hannah Montana & Miley Cyrus: Best Of Both Worlds."

Already she was trying to change her image from being that wholesome teen on her show. The Breakout singer started getting edgier by dying her hair dark with fashionable locks, a move meant to individualize herself from the “blonde girl” Hollywood look. It was the start of the Anti-Hannah period.

12 2008 - The Vanity Fair Cover Shot

It's a major coup for a celebrity to appear on the cover of Vanity Fair, and to be shot by famed photographer Annie Leibovitz is also a dream. That's what happened to Miley Cyrus who was at the height of her fame. But the shot backfired.

In the now notorious cover shot, Cyrus is looking over her shoulder while holding up a satin sheet over herself. She appears to be shirtless because her bare back is displayed. VF is infamous for its provocative images of celeb women appearing nearly nude on the covers. But the problem was, Cyrus was still a teen, which was why 2008 was the year where she drew a lot of controversy for showing skin, something she would do later in a sexy and a more exaggerated way.

11 2008 - The Vanity Fair Cover Shot Backlash

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From Disney’s biggest star to pop music’s most scandalous It Girl, over the last decade Miley Cyrus has changed her image in so many ways to show that she was growing up. This not only confused her target audience but also backfired in a big way. The VF was an early example.

Miley was the 15-year old star of a Disney Channel show, a girl who was supposed to be a role model for young girls when the VF issue appeared. Of course, the network was furious and claimed the photo tainted her image and that VF "deliberately manipulated" Cyrus into posing apparently topless to sell magazines. VF defended the shot, insisting that Cyrus and her family were happy with it. Leibovitz also defended the photo, saying it was “artistic.” Cyrus herself backed up the near topless shot by saying in VF, “I had a big blanket on. And I thought, this looks pretty, and really natural." But later on, her story changed. When the photograph was made public, she said,

"I took part in a photo shoot that was supposed to be 'artistic' and now, seeing the photographs. . . I feel so embarrassed. I never intended for any of this to happen and I apologize to my fans who I care so deeply about."

10 2008 - Controversy Ensues Again

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Cyrus didn’t need to court any more controversy after the VF photo scandal began to cool down. But in July 2008, leaked photos of the “Party in the USA” singer and actress began to pop up on the internet showing her in compromised positions that were originally intended to be seen only by her then-boyfriend Nick Jonas, who too was on the Disney network and would emerge later as one of the channel’s hottest heartthrobs.

The selfie photos included Cyrus in a bikini and midriff and her wearing only a wet T-shirt that left little to the imagination. But Cyrus—as well as Jonas—fanned the flames by famously wearing purity rings and spoke openly about their choice to abstain from sex until marriage. This time there was no backfire.

9 2008 - Gowns And Glitter, As Well As Back To Basics

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Cyrus once again changed her image in 2008 by covering herself up and wearing beautiful designer gowns and dresses at every award show and red carpets. At the Teen Choice Awards, she wore a sophisticated dress decked out with her favorite feature: sequins. At the AMAs, she appeared in a black and gold sequined dress. But it was at the Academy Awards, where she was a first-time presenter, when Cyrus turned into a very mature teen by wearing a knock-out, floor-length red gown paired with glittering earrings. That same year, she pushed that image further and showed cleavage for the first time, showing off her chest in a black and gold dress by Marchesa at the American Music Awards.

But off the red carpet, Cyrus began channeling her early years as Hannah Montana again by wearing funky vintage clothing that bordered on the tacky, such as when she wore a graphic T-shirt, black leggings, pointed booties, a studded belt, and to top off this strange look, a hot-pink driving hat that she sported on MTV’s TRL. She was also back to basics by wearing even more sequin-covered dresses, cowboy boots and colorful flowy tops.

8 2009 - Pushing The Boundaries For the First Time

Us Weekly

The VF cover now seems tame compared to Cyrus’ appearance on the Teen Choice Awards in 2009. In a risqué performance that would go down in history as the time Cyrus displayed her burgeoning sexuality, she appeared scantily clad while pole dancing to her mega-hit “Party in the U.S.A.,” which would launch her into an internationally-recognized bona fide pop star.

Wearing black denim cutoffs with a grungy tank that exposed her black bra, Cyrus gyrated on a pole with plenty of suggestive moves and pelvic thrusts. The performance once again caused controversy for Cyrus, with media and pundits wondering if it was appropriate for a star who was still an under-aged teen. Cyrus stopped short of a striptease and this time Disney made no public comments about the controversy.

7 Early 2009 - Sophisticated And Mature

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In 2009, after her notorious pole dancing performance at the Teen Choice Awards, Cyrus changed again and began wearing demure yet sophisticated dresses and gowns that put her on many best-dressed lists. This was the first time that audiences, fans and the media agreed with what Cyrus was wearing.

She started showing off in couture gowns, such as one made by Zuhair Murad, which she wore at the 2009 Academy Awards. She wore a free-flowing white gown by Marchesa at the 66th Annual Golden Globe Awards. At the Grammy’s that year, the 16-year old looked like a starlet in a black asymmetrical dress from Herve Leger by Max Azria. In one of her best outfits of that year, Cyrus wore a chic dress that was sophisticated but at the same time seemed age-appropriate, as the white Dolce & Gabbana dress had a butterfly-print on it with ruffles that made her look very feminine, a look that Blair Waldorf would approve of. She sported that look for the "Hannah Montana: The Movie" premiere in Paris in April 2009.

6 2010 - Coming Into Her Own


2010 was the year that Cyrus, now 18, started to come completely into her own, style-wise. She once again wore outfits that were not age-appropriate, such as a super sexy denim Herve Leger by Max Azria Spring 2010 dress that she paired with black strappy Balenciaga sandals. She also wore a scantily clad crop top that showed too much of her belly that she sported with barely-there bootie shorts, another risqué outfit for someone who was still technically a teen.

The looks would turn out to be a precursor for the more daring fashion turns that she will always be known but probably will end up regretting. We guess you need to be a rebel for a while as a teen before you really do come into your own.

5 2010-2012 - Old Hollywood Glamour


2010 was also the year where Cyrus once again changed her looks, this time opting for an Old Hollywood glamour look. The defining change was seen when Cyrus appeared at the Academy Awards. Cyrus wore a strapless shimmering gold Jenny Packham gown with upswept hair, which would go down in Miley Cyrus history as one of her most iconic and age appropriate looks.

On the red carpet again, Cyrus was covered from head to toe in a long-sleeve body hugging gown that gave way to a long train that she paired with red lipstick and retro waves. These images made Cyrus look as if she just stepped out of a 1950s movie, and these defining years would become her best, non-controversial looks. She was a girl coming into her own not as an eye-popping wild woman, but rather as a woman who need not show skin to get attention. Too bad 2012 was the end of the era before Cyrus once again changed into the bad girl that we all know.

4  2013 - From ‘50s Starlet To Foam Fingers


It was the beginning of a new era. Cyrus came out with a new album called Bangerz along with a new look that took her from glamorous fashion icon to provocative sex symbol. She dyed her long hair blonde and shortened it into a punk pixie cut and started to wear outlandish, near-nude outfits. Her transformation from Disney princess and girlish Hannah Montana to fashion provocateur was complete. It was during the 2013 MTV VMAs that Cyrus first showed us her inappropriate side as well as her most controversial look ever in the short history of her public life.

Singing “We Can’t Stop,” with her now-famous tongue dangling out and wearing a one-piece spandex suit that left her looking completely nude, Cyrus, then 20, twerked her way around the stage before being joined by singer Robin Thicke. She then would make infamous headlines that never died down and shocked the audience by stripping further to a nude latex bra and panty combo while suggestively touching herself and touching Thicke, who is much older than her (he was 36 at the time), with a foam finger. She continued to bump and grind him and drape herself all over him as Thicke started to sing his hit single “Blurred Line,” while wearing a more appropriate outfit, a black-and-white striped suit.

That same day, Cyrus released her single “Wrecking Ball,” the second single from Bangerz, which became an instant hit. It too was met with controversy because the video of the single showed her swinging naked on a wrecking ball, which the media found cringe-worthy.

3 2015 - Crazy Wardrobes


Then Cyrus got weirder. She was seen in LA wearing bunny ears and a striped jumper with a rabbit on the front. The animal-theme ensemble actually started at the VMAs during her twerking appearance in 2013. While performing “We Can’t Stop,” Cyrus climbed out of a giant teddy bear wearing a furry bustier designed to coordinate with the teddy bear theme.

She was also accompanied by dancers wearing giant teddy bear costumes. At one point she grabbed a dancer’s teddy bear ears before bending over to shake her butt at the audience. The whole performance and outfit were surreal. At a charity event in LA in 20015, Miley wore an oversized flower costume on her body.

2 2015 - Controversy Again At The MTV VMAs

TV Guide

In 2015, Cyrus hosted the MTV VMAs two years after her controversial twerking performance. She appeared throughout the night nearly nude. And before the VMAs, she shared with her fans a nude selfie that she posted on Instagram. And then, on the red carpet, Cyrus actually wore clothes, if you could call it that. She wore an upper-body silver piece with suspenders that barely covered her breasts and little else. For her bottom, she wore a jeweled beaded “skirt” that hung strategically over her private parts that made her look like a crystal chandelier.

That same evening, she proudly wore a plastic see-through dress with white tall boots and buttons in various sizes and colors to cover all the right places. And then, to the surprise of many, Miley appeared covered up but still crazy-looking like from her animal-outfit days by wearing a box-like LGBT pride-inspired flag that made her look like a kite. It’s great that Miley supports the LGBT community (as well as women’s rights and the rights of all different people), but she has a funny way of showing it!

1 2016-2017 - A 180 Return To Her Roots

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In 2016, Cyrus signed on as a coach for the eleventh season of the TV show The Voice.  This was the start of a return to her roots, that of a part bohemian, part hippie urban chic who wore splashy-colored prints and didn’t in any way show too much skin. Some said it was another end to an era, as the starlet seemed to have reverted to her Hannah Montana persona.

This came about when she rocked The Voice sporting a jean jacket decorated with giant flowers on a few episodes, as if she was the girl next door. She was no longer the girl dancing on poles, nor the girl barely legal who was doing naked photoshoots, nor was she the girl dancing on a man twice her age.  Finally, we got Miley back.

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