Miley Cyrus Leaves ‘Hannah Montana’ Behind With Daring Style Transformation

Miley Cyrus happens to be one of those Hollywood royalties whose style evolution has been dynamic and a reflection of the various phases of her life. One could also witness a tint of her bold and vivacious persona in her sartorial choices over the years.

The singer-actress rose to fame as a child star and singer on Disney Channel hit show, Hannah Montana. She played a pop star who lived a double life and is on a constant quest to conceal her identity.

Apart from her performance and vocals, Miley became a trendsetter because of her outfits on the show. Her ensembles looked straight out of a Pinterest mood board of a teenager.

Blingy dresses, printed tees dominated by pink, skinny jeans and a stylish denim jacket, the Wrecking Ball hitmaker did it all.

Some of her outfits also included loose and baggy tops coupled with leggings which screamed snug and cozy. Every Miley fan out there can bask in the nostalgia of her “The Best of Both Worlds” era.

Soon after her Hannah Montana series ended, Miley inevitably began to establish herself as a mainstream commercial artist, but she was thrust into controversies and scandals. From her family rift to battling drugs and alcohol to sporting “inappropriate outfits”, The Flowers singer entered her “Bangerz” or “Dead Petz” era. Her bold and raunchy ensemble at the 2013 iHeart Radio Music Awards had her donning an all-white sleeveless lace crop top, which she paired with hot pants that drew comparisons to a diaper.

However, cut to her 2026 iHeart Radio Music Awards outfit, The Last Song star’s outfit transformation has been jaw-dropping and also reflects her evolution as a person. Years later, for the same event, Cyrus opted for a long-sleeved black top with button details and matching leather pants. She went for a dewy makeup with her hair kept down in waves, which was again a stark contrast to her bold makeup in the 2013 event.

If by any chance her black pantsuit outfit comes across as boring to some people, trust the Party In The U.S.A singer to add a sprinkle of fun. At the Hannah Montana 20th Anniversary special premiere, Miley added a striking combination of nostalgia and creativity in her ensemble.

She went for a silver floor-length dress with a midriff cutout and matching heels. However, the highlight of the outfit was the picture of her alter ego, Hannah Montana, on her chest that seemed to be made out of a vintage t-shirt. The singer also went for her iconic blonde Hannah Montana bangs hairstyle. She managed to both give a tribute to the character that catapulted her to superstardom, but kept her personal style statement intact.

In a 2021 interview with Vogue, Miley Cyrus described her fashion and style evolution saying, “Fashion to me is kind of flipping yourself inside out. It’s like wearing your heart, wearing your guts, wearing your values, wearing your identity, wearing your pain, wearing your joy. There’s something kind of childlike [about it]. You’re so fearless when you get yourself dressed when you're a kid. You don't think about what someone will think of you or what they’ll judge. It’s just about expression and how you feel that day. There’s a fearlessness. And so when I get dressed, I try to kind of think like my inner child, and be genuine and authentic in whatever I’m wearing.”