Miley Cyrus has long been known for her bold and ever-changing hairstyles, often embracing new looks that match her mood. In a 2016 Facebook post, the singer shared a refreshing carefree approach to hair transformations. “If a change feels right to you — f***ing DO IT! Don’t overthink it,” she wrote. “In the end, it’s just hair and nothing you do is detrimental. It’s just a new chapter!” Her playful attitude toward hair has made her a hair chameleon, rocking everything from a short blond pixie cut to long, flowing brunette waves. She’s even turned heads with some of the most memorable award show hairdos.
However, not all of Cyrus’ hair experiments have been hits. One early look that raised eyebrows involved 250 hair extensions. In an interview with Harper’s Bazaar, Cyrus revealed that her mother, Tish Cyrus, insisted on adding more extensions, saying, “If it was under 250, my mom wasn’t having it. We need another row.” Cyrus also noted that the heavy extensions might have damaged her natural hair, adding, “The kind of hair extensions we had, they don’t even do these anymore.” While extensions can enhance volume and length, too many can cause discomfort and, if applied incorrectly, may lead to hair loss.
In 2025, Cyrus made waves at the Vanity Fair Oscar Party with a pulled-back style featuring short bangs. While bangs can add a vintage touch, her uneven, choppy version didn’t quite complement her face shape. Fans on social media voiced their opinions, with one user writing, “Why are some Smilers confidently lying about Miley’s bangs looking good? Like no, it doesn’t.”
At the 2024 Grammys, Cyrus stirred up attention with chest-length, voluminous caramel brunette hair styled with intense Velcro rollers. However, the result looked more like windswept hair from a car ride rather than a carefully styled do. Her hairstylist, Bob Recine, explained the look was inspired by a ‘70s Barbarella vibe mixed with a modern punk edge. Despite the intention, the style didn’t quite hit the mark and felt more dated than trendy.
One of Cyrus’ most notable hair missteps came in 2013, when she tried the fringe bob, which was trendy that year. At the 24th Annual KROQ Almost Acoustic Christmas event, her choppy, graduated bob and light toffee-colored highlights made her appear older than her 21 years. A sleeker, blunter bob might have made the look feel more youthful and modern.
In 2016, Cyrus went platinum blonde with small buns and long bangs at a basketball game. The style itself wasn’t necessarily bad, but she later regretted it, admitting on Facebook that she used a box dye at home. “Either this st needs to grow out at super speed or I’m about to go in for a fkin’ haircut realllllll quick!!!” she wrote. While box dye can sometimes work in a pinch, Cyrus’ regret highlights the importance of professional styling to prevent potential hair damage.
Lastly, at the 2012 MTV Video Music Awards, Cyrus tried a bold stand-on-end style that didn’t quite work. With super-short sides and a pompadour in the center, her hair was heavily sprayed, making it look unnaturally crunchy. One fan tweeted, “This look that you showed at the VMA’s doesn’t work for you.”
While Miley Cyrus’ hair transformations are often daring and creative, not every look has been a success. Nonetheless, her willingness to experiment continues to make her a standout in the world of celebrity style.
