Ask Miley Cyrus fans what they love most about her, and many will probably mention her carefree attitude and commitment to marching to the beat of her own drum. Of course this is reflected in the music she puts out — her oeuvre ranging from rap collabs to anthemic pop and beyond — but you can see it in her sense of style, too. In fact, looking back on the “Flowers” singer’s history of red carpet moments as well as performances, her hair follows as similar trajectory as her career. That’s because, following the lead of pop icons like Madonna or Lady Gaga, there’s a 360 approach to the art she makes. And yes, hair and makeup are integral to the entire mood. That said, it’s not surprising that Cyrus’ best hairstyles ever go hand-in-hand with momentous moments in her life.
From her Y2K chunky highlights portraying Hannah Montana to this year’s Barbarella-inspired blowout at the Grammys, Cyrus has had so many notable hair moments throughout her nearly 20 years in the spotlight. And at only 32, she’s got many decades left to keep them coming. While we wait for her next iconic hairstyle, we’re revisiting some of her finest to date — not only the aforementioned ones, but all the micro bobs, baby bangs, and spiky pixies in between.
Windswept Waves, 2024
The Endless Summer singer stunned at the 2024 Grammy Awards with her voluminous, highlighted blowout, which channeled Raquel Welch’s character in Barbarella. The hairstyle was so fitting for her two glam rock looks at the event, a mesh custom Maison Margiela on the carpet and vintage Bob Mackie on stage.
Contrasting Color, 2023
Cyrus brought back the mid-aughts two-tone hair (dark brunette underneath with platinum on top) while attending the Versace show in Los Angeles last year.
Platinum Beach Waves, 2022
She may be a Tennessee girl at heart, but the “Midnight Sky” singer was giving all the Malibu vibes with platinum blonde beach waves for a New Year’s Eve performance in 2022.
Fluffy Curls & Dark Roots, 2021
Cyrus was totally channeling one of her music idols, Debbie Harry, when she attended the 2021 LACMA Art + Film Gala in fluffy, bright blonde curls with nearly black roots.
Wispy Mullet, 2020
Like father like daughter. In 2020, Cyrus adopted dad Billy Ray’s iconic mullet — but she made it a little less country and a lot more rock and roll for Tom Ford’s fashion show.
Baby Bangs, 2019
The singer and actor debuted freshly-snipped bangs while attending the Met Gala in 2019. The wispy style paired with long, straight golden blonde hair was a perfect match for her edgy-cool Saint Laurent sequined mini dress.
Soft Side-Swept Waves, 2018
The rocker took a break from her more grunge-inspired styles to have an Old Hollywood glam moment with soft, side parted waves at the 2018 Grammy Awards.
Two-Tone Top Knot, 2016
The Younger Now singer’s long dark roots gave her messy top knot a cool two-tone effect for the Crisis in Six Scenes premiere in New York City.
Glittery Blue Micro Bob, 2015
Cyrus was the epitome of rebellious glam (her brand, really) while attending the 2015 Met Gala. The Bangerz singer topped off her studded dress with a slicked-back blue bob with a glitter-dusted side part.
Spiky Pixie, 2013
At the previous year’s Met Gala, Cyrus created yet another iconic hair moment. This time, she perfectly embodied the event’s punk theme with an undercut pixie topped with spiky strands.
Beachy Side Braid, 2011
The The Last Song star showed up to the 2011 CNN Heroes All-Stars Tribute with a chunky side braid that gave a beachy feel to her floaty yellow gown.
Windswept Updo, 2010
At the 2010 Oscars, the Can’t Be Tamed singer debuted a grown-up glam look complete with a windswept updo that complemented her strapless satin dress.
Chunky Blonde Highlights, 2007
You simply can’t have a “best Miley Cyrus hairstyles” list without including her Hannah Montana-era chunky highlights. The Disney star’s look was so iconic, she’s actually been sporting similar styles recently.
