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.
