Hands Down, Miley Cyrus Has Had the Most Dramatic Beauty Evolution of the Past Decade
On Hannah Montana, you could always expect Miley Stewart to be brunette by day and blonde by night. On the red carpet, you can never know what to expect from Miley Cyrus. The 26-year-old pop star has had a wild style evolution over the nearly 14 years since Hannah Montana first debuted, and her beauty looks have changed just as much as her wardrobe choices. From glitter and hair extensions to pixie cuts and red lips, Cyrus has debuted every color and cut imaginable, and we applaud her for always being willing to take a risk. Let's review how her hair and makeup have evolved over the years, shall we?
Miley Cyrus at The Disney Channel 2006 Winter UpFront in February 2006
A baby-faced Cyrus appeared at one of her first Hannah Montana events with her natural brunette hair in barrel curls and barely-there makeup.
Miley Cyrus at a Disney World Meet-and-Greet in June 2007
Just a year later, Cyrus embraced a darker hair color and extensions, which she styled in spiral curls. Though she still sported minimal makeup, she did play up her features with a touch of shimmery highlighter.
Miley Cyrus at the Teen Vogue Young Hollywood Party in September 2007
Cyrus sported a high ponytail long before Ariana Grande did at this Teen Vogue party, which looked even sweeter with long, side-swept bangs. The best part of her look: those cherry red lips.
Miley Cyrus at the 35th Annual American Music Awards in November 2007
At the 2007 AMAs, Cyrus debuted Kelly Clarkson-esque chunky blonde highlights in her flat-ironed hair, completing the look with thick black eyeliner and clear lipgloss.
Miley Cyrus at the 50th Annual GRAMMY Awards in February 2008
Cyrus brought her longest extensions, darkest hair shade, and thinnest brows yet to the 2008 Grammys, where she complemented her hair with nude lipstick and smokey blue eye makeup.
Miley Cyrus at the 80th Annual Academy Awards in February 2008
At the 2008 Oscars, Cyrus looked adorably polished with chestnut hair, elegant side-parted updo, rosy cheeks, glittery cheekbones, and subtle lip color.
Miley Cyrus at the City of Hope Benefit in September 2008
Cyrus switched it up again at this 2008 benefit with eyebrow-grazing bangs, honey-blonde highlights, and kohl-rimmed eyes.
Miley Cyrus at the 2009 MTV Movie Awards in May 2009
For the 2009 MTV Movie Awards, Cyrus decided on a chic, low pony with tons of cascading curls and face-framing side bangs. To complete the look, she donned dark liner and clear gloss.
Miley Cyrus at the 52nd Annual GRAMMY Awards in January 2010
At the 2010 Grammys, Cyrus debuted a new pretty auburn hair color, which she wore in loose waves. She completed the look with majorly bronzed cheeks, dramatic eye makeup, and nude lips.
Miley Cyrus at the 21st Annual MuchMusic Video Awards in June 2010
Cyrus said goodbye to her hair extensions for the 2010 MuchMusic Video Awards, where she brought her A-game with shoulder-length copper curls, jet-black liner, and smokey purple shadow.
Miley Cyrus at the 2010 MTV Europe Music Awards in November 2010
The extensions were back for the 2010 MTV Europe Music Awards, where Cyrus sported bright blonde waves and dark roots with shimmery brown shadow.
Miley Cyrus at the American Giving Awards in December 2011
At the first-ever American Giving Awards, Cyrus arrived with a sleek extra-long pony, which dramatically transitioned from deep brown at the roots to platinum at the tips. To complete the look, she added plenty of highlighter and slightly thicker brows.
Miley Cyrus at the 20th Annual Elton John AIDS Foundation's Oscar Viewing Party in February 2012
Cyrus brought old Hollywood glamour to the AIDS Foundation Oscar Viewing party with a bold cat eye, bright red lips, defined brows, and a curled ombré faux bob.
Miley Cyrus at the 2012 MTV Video Music Awards in September 2012
Perhaps Cyrus's most dramatic beauty debut, this platinum blonde double-undercut — which was teased into a faux-hawk — turned heads at the 2012 VMAs. She kept her makeup subtle with a sweep of pink shadow and baby pink lips.
Miley Cyrus at the Seacrest Studios Debut in March 2013
Cyrus made her cheekbones pop with this tousled platinum-blonde pixie cut and side-swept bangs at the Seacrest Studios debut, especially when she added a bright red lip color and soft purple eyeshadow.
Miley Cyrus at the 2013 Met Gala in May 2013
Cyrus took the 2013 Met Gala's punk theme seriously with a gravity-defying platinum spiked 'do, which she paired with surprisingly minimal eye makeup and crimson lips.
Miley Cyrus at the Opening of Britney: Piece of Me in December 2013
This two-tone pixie cut that Cyrus sported at the Britney: Piece of Me opening was made extra-cool with a deep side part and voluminous side bangs. As always, Cyrus brought her cherry-red pout and chunky mascara.
Miley Cyrus at the 2014 amfAR Inspiration Gala in October 2014
To amp up her spiky platinum pixie cut at the 2014 amfAR Gala, Cyrus went dramatic with a gray shadowy cat eye, chunky mascara, and a glossy nude lip.
Miley Cyrus at the 2015 Met Gala in May 2015
At 2015's Met Gala, Cyrus arrived with a slicked-back bob dyed an icy-blue color for the night, which she paired with bronzer and barely-there eye makeup.
Miley Cyrus at the 2015 MTV Video Music Awards in August 2015
Cyrus's wild look for the 2015 VMAs included long braided extensions, a sky-high pony, and electric-blue eyeliner.
Miley Cyrus at ONE Campaign and (RED)'s 10th Anniversary in December 2015
Cyrus grew out her pixie cut for this 2015 anniversary event, where she wore her shoulder-length ombré 'do slicked back with a deep side part, completing the look with some fun sparkles at the roots and soft pink eyeshadow.
Miley Cyrus at The Elvis Duran Z100 Morning Show in May 2017
Cyrus was a little bit country at The Elvis Duran show in 2017, where she wore a boho hat over her bleached-out beach waves and minimal makeup.
Miley Cyrus at the 60th Annual GRAMMY Awards in January 2018
At the 2018 Grammys, Cyrus wore her golden hair in vintage waves and very little makeup, save for some powder-pink blush and a sweep of shimmery shadow on her lids.
Miley Cyrus at the 2018 Vanity Fair Oscar Party in March 2018
For the 2018 Vanity Fair Oscar Party, Cyrus brought back her signature loose waves with this pretty curled bob, and she kept her makeup subtle save for her bright red lip color.
Miley Cyrus at the Avengers: Endgame Premiere in April 2019
At the Avenger: Endgame premiere, Cyrus channeled Hannah Montana with pin-straight eyebrow-grazing bangs and soft blonde barrel curls.
Miley Cyrus at Saint Laurent's Spring 2020 Menswear Runway Show in June 2019
One of Cyrus's latest looks included choppy bangs, defined brows, blue winged shadow, and her now-signature crimped wet hair.