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  • At the 2006 Academy of Country Music Awards, Miley Cyrus donned a purple, beaded dress that would totally inspire all the middle school mean girls for their 8th grade formal.Photo by Getty Images
  • At the Monster House premiere in July 2006, Cyrus dared bare some upper calf. Racy.Photo by Getty Images
  • For the 2008 Grammys, the then-Hannah Montana actress attempted a more grown-up look in white Celine—a simple dress that perfectly accentuated her weirdly orange skin and lengthy extensions.Photo by Getty Images
  • At the 2009 Academy Awards, the pop star bounced back to her squeaky clean image in Zuhair Murad, channeling a glitzy mermaid instead of off-duty Lindsay Lohan.Photo by Getty Images
  • At a 2009 premiere of the Hannah Montana Movie, the singer-actress paired a neon pink blouse with a bohemian leather necklace, boot cut jeans, and platform sandals—a look that was undoubtedly celebrated across Tween-America.Photo by Getty Images
  • At the December 2009 Jingle Bell Ball, Cyrus paired studded combat boots with metallic accessories and shimmering hot pants. A sassy hand-on-hip pose completed this I’m Not A Starlet, Take Me Seriously look.Photo by Getty Images
  • Anne Hathaway, is that you? At the 2010 Academy Awards, Cyrus donned a princess-y, floor-length Jenny Packham gown and a classic up-do that forced us to do a retroactive double take.Photo by Getty Images
  • With Hannah Montana in her not-so-distant past, the starlet showed some still-tattoo-less skin at the 2011 CNN Heroes event in a low-cut Roberto Cavalli dress. Unpictured: a sign that read, “I’m up here.”Photo by Getty Images
  • In 2012, the uneven hemline was totally ubiquitous, so the singer naturally paired her Jenny Packham gown with a dark tan and ombre curls for Muhammad Ali’s Celebrity Fight Night in March. Because three overdone trends are better than one.Photo by Getty Images
  • A teased coif this elaborate must have left Cyrus with little time for unimportant activities like pairing pants with her white Jean Paul Gaultier jacket at the 2012 Billboard Music Awards. Blame the hairspray.Photo by Getty Images
  • For the 2013 premiere of Paranoia, Cyrus showed off her ladylike side with a mod, patchwork leather Proenza Schouler dress and white Celine pumps. And no, before you ask, they are not the same ones that she wore in 2008. Clearly.Photo by Getty Images
  • At her 2013 Bangerz Record Release party, Cyrus donned a white crop top, overly distressed white jeans, and classic black-and-white creepers. And the icing on the monochromatic cake? Black star-shaped pasties that would make even Lil Kim jealous.Photo by Getty Images