Miley Cyrus is known for her ever-evolving hair, embracing bold changes from pixie cuts to long waves. In a 2016 Facebook post, she shared her philosophy on hair transformations, encouraging her fans to take the plunge and not overthink their choices. But, despite her often fearless approach, some of her hairdos have left us questioning her decisions.
One example that stands out is the 250 hair extensions she wore in her early career. Cyrus admitted to going overboard with extensions, telling Harper’s Bazaar that her mom insisted on adding row after row. While hair extensions can create stunning volume, too many can cause discomfort and potential damage to natural hair. With such heavy extensions, it’s no surprise that Cyrus later regretted this look, especially given the risks of hair loss.
2025 Oscars Bangs: A Miss
At the 2025 Vanity Fair Oscar Party, Miley sported short, choppy bangs, styled by Bob Recine on the way to the event. While micro bangs can be cute, this uneven, rushed look didn’t suit her face shape, with some fans expressing disappointment on social media.
2024 Grammys: Windswept Hair Disaster
At the 2024 Grammys, Miley’s voluminous caramel brunette hair was styled with a retro ’70s feel, but the result was more “windswept” than “chic.” Despite the intention for a modern, punk-inspired look, the tousled appearance of her chest-length locks made it seem like she’d forgotten to close her car roof before arriving at the event.
2013 Choppy Bob and Bangs: Too Aged
Cyrus’ attempt at a choppy bob with bangs in 2013 made her look older than her years. The uneven cut, combined with lighter blonde highlights, washed her out, and we felt it was a missed opportunity. A sleeker, more modern bob could have given her a youthful, edgy look instead.
Bleach Blonde Regret
In 2016, Miley went platinum blonde, pairing it with small buns and long bangs. While the style itself wasn’t bad, she quickly regretted it after using at-home box dye, admitting on Facebook that she couldn’t wait for it to grow out. While at-home dye jobs can work in a pinch, it’s always better to leave this to the professionals to avoid unnecessary damage.
2012 VMA Stand-Up Style: Too Much Product
At the 2012 MTV Video Music Awards, Miley attempted a bold stand-up style with her super-blond hair and a pompadour, but the look didn’t quite land. The heavy gel and spray made her hair appear stiff and crunchy, which led fans to criticize it as too much.
Miley’s hair has always been an expression of her ever-changing personality, and while some looks are iconic, others will forever be etched in the “hair don’ts” category.
