Miley Cyrus Hair Looks That Had Us Cringing

Miley Cyrus shared a refreshing take on her ever-changing hair in a 2016 Facebook post after dying her own locks. "If a change is something that feels right to you — f***ing DO IT! Don't over think it because in the end it is f***ing hair and nothing you do is detrimental and will just be a new chapter for you!" she wrote. "My life is done chronologically in hair styles lol !!!!" And she wasn't wrong. This hair chameleon has sported everything from a short blond pixie to long, brunette waves. Cyrus has also been seen rocking some of the coolest award show hair looks of all time. But while we agree there's nothing wrong with matching your tresses to your mood, there are a few occasions a new chop, style, or color just didn't work for the former Disney Channel darling.

Take the overkill of 250 hair extensions she wore in the early days of her career, for example. Speaking to Harper's Bazaar, the "Can't Be Tamed" hitmaker shared, "It if it was under 250, my mom wasn't having it. Tish [Cyrus] was like, we need another row. Tish would be like, dig another row up." To make matters worse, the Tennessee native suggested the strands may have damaged her natural tresses, adding, "The kind of hair extensions that we had, they don't even do these anymore." Yikes. The reason this look made us cringe? All that weight on her head couldn't have been comfortable and incorrectly applied, extensions can potentially lead to hair loss. Though we're sure Cyrus had a great team on-board to prevent damaged locks, the more extensions, the more chance for things to go wrong. And there are a few other hair dos (or don'ts) from "The Last Song" actor we weren't sold on either.

At the 2025 Vanity Fair Oscar Party, Miley Cyrus sported a pulled back 'do with short bangs. Bob Recine actually cut the bangs on the way to the event — and it showed. Though micro bangs can bring a vintage flair to your haircut, Cyrus's choppy, uneven take coupled with her bleached brows didn't compliment her face shape. Not everyone was feeling the look on social media either, with one X, formerly known as Twitter, user writing, "Why are some Smilers confidently lying about Miley's bangs looking good ?? Like no it doesn't."

Miley Cyrus caused a stir at the 2024 Grammys. Her chest-length, voluminous, caramel brunette locks tresses were pushed back, with intense Velcro roller volume. The problem was it looked like she'd had the top of her vehicle down on the way to the event as the hair appeared windswept — not like she had a carefully styled 'do. "[We wanted] a style that felt like it had a '70s, Barbarella feel while still having a modern, punk edge," her hairstylist Bob Recine told People, but the result looked dated.

Though the fob (aka the fringe bob) was the most iconic hair look of 2024, when Miley Cyrus tried it in 2013, it made us cringe. Her choppy, graduated take at the 24th Annual KROQ Almost Acoustic Christmas event aged her (she was only 21) and the blond highlights and light toffee color washed her out. To make the look more youthful, we'd have cut a blunter bob with less tapered ends a la the sleek French bob for a chicer, more modern style.

In 2016, Miley Cyrus rocked platinum blond locks in small buns with long, full bangs at a basketball game. This style had us cringing not because it looked bad, but because of how much she regretted it. Cyrus wrote on Facebook she'd used an at-home box dye, and admitted, "Either this s**t needs to grow out at super speed or I'm about to go in for a f**kin hair cut realllllll quick!!!" Though box dyes can work in a pinch, we'd always recommend going through a stylist to avoid potential hair damage.

Though we love Miley Cyrus' dedication to changing her locks, when she went for a stand on end style at the 2012 MTV Video Music Awards, her strands were a little too long to work. Her hair was super blond with very short sides and her stylist created a bold pompadour in the center of her head, but all the spray/gel made it look unnaturally crunchy. One fan tweeted, "This look that you showed at the VMA's, doesn't work for you."