Hannah Montana, the early years, lived in the quintessential Y2K wardrobe — ripped, bootcut denim, matching vests, capris leggings, cropped jackets and all the half-shirt, half-dress options she could get. The first episode of the Disney Channel show saw Miley Cyrus enliven her popstar persona with a feathered blond wig. It wasn’t until the second episode that Hannah introduced her signature straight ends with bluntly-cut forehead bangs.
Clad in complementary colors and clashing patterns, the star experimented with her style and a cropped hairdo from 2008 to 2009. Here, Hannah swapped her skinny scarves and bedazzled suit ties for the infamous, hot pink Michael Jackson glove, a teddy bear (IYKYK) and wide-brimmed belts. She also favored the recently revived socks-with-heels trend, pairing pink hoisery with platform wedges.
By 2010, her inner punk and penchant for pattern-maxxing had subdued. In its place, a bohemian pop princess blossomed. Her wardrobe had all the same elements it always had, only now she wore ruffles, fringe, ankle boots, Minnetonkas and layered necklaces. Hannah’s hair was also back to its original length but wavy instead of straight. Her fringe was also less harsh (think blended).
Fans wouldn’t see Hannah for the next 10-plus years but rumors of her return swirled. Finally, at the 2026 Grammys in February, Cyrus confirmed the upcoming 20th anniversary special, with a nod to her other half.
Ahead of the anniversary premiere on March 24, WWD is taking a look back at the evolution of Hannah Montana’s beauty and style.
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Hannah Montana Through the Years
Image Credit: Disney General Entertainment Con The first Hannah Montana billboard for “You’re So Vain, You Probably Think This Zit Is All About You.”
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Hannah Montana Through the Years
Image Credit: Stephen Shugerman Hannah Montana onstage at the Hollywood Radio and Television Society “Kids Day 2006.”
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Hannah Montana Through the Years
Image Credit: WireImage Hannah Montana at the Gibson Amphitheatre in Universal City, California.
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Hannah Montana Through the Years
Image Credit: WireImage Hannah Montana during the “Miley Cyrus/Hannah Montana: Best of Both Worlds” Tour in 2007.
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Hannah Montana Through the Years
Image Credit: WireImage Hannah Montana during “Miley Cyrus/Hannah Montana: Best of Both Worlds” Tour in 2007.
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Hannah Montana Through the Years
Image Credit: WireImage Hannah Montana during her “Miley Cyrus/Hannah Montana: Best of Both Worlds” Tour in 2007.
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Hannah Montana Through the Years
Image Credit: WireImage Hannah Montana on location for “Hannah Montana: The Movie” filming on the Santa Monica Pier in 2008.
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Hannah Montana Through the Years
Image Credit: Disney General Entertainment Con Promo for Disney Channel’s “Hannah Montana” in 2008.
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Hannah Montana Through the Years
Image Credit: Disney General Entertainment Con Additional promo fo Disney Channel’s “Hannah Montana.”
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Hannah Montana Through the Years
Image Credit: Disney Channel via Getty Images Season three of “Hannah Montana,” episode “Come Fail Away” in 2009.
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Hannah Montana Through the Years
Image Credit: Disney General Entertainment Con Season four of “Hannah Montana, episode “It’s The End of The Jake As We Know It” in 2010.
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Hannah Montana Through the Years
Image Credit: Disney General Entertainment Con Season four of “Hannah Montana,” episode “Hannah’s Gonna Get This” in 2010.
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Hannah Montana Through the Years
Image Credit: Disney General Entertainment Con Season four of “Hannah Montana,” episode “Been Here All Along” in 2010.
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Hannah Montana Through the Years
Image Credit: Disney General Entertainment Con Season four of “Hannah Montana,” episode “I’ll Always Remember You” in 2010.
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Hannah Montana Through the Years
Image Credit: Disney General Entertainment Con Series finale of “Hannah Montana” in 2010.
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Hannah Montana Through the Years
Image Credit: Billboard via Getty Images Miley Cyrus teases her return to Hannah Montana at the 68th Grammy Awards in February with a subtle hair transformation.
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Hannah Montana Through the Years
Image Credit: WireImage Miley Cyrus attends the World Premiere Of Disney+’s “Hannah Montana 20th Anniversary Special” in Los Angeles