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Then: Hilary Duff

Butterfly clips, scrunchies, all the looks of our tweenage fashion dreams: Hilary Duff won us over as Lizzie McGuire in the early 2000s. From the super expensive bedazzled jeans she bought without her mom's permission to her matching bandanas and leather jackets, the teen's Disney show was filled with plenty of must-copy fashion moments—but her off-screen outfits were just as defining.

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Now: Hilary Duff

Currently the star of TV Land's Younger, Duff's style has come a long way from her Lizzie McGuire days. While the actress still favors trend-forward ensembles, she's managed to perfect the effortlessly chic West Coast look over the years.

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Then: Raven Symone

Though starring on Disney's That's So Raven in the mid-aughts was hardly Raven Symone's introduction to television, the teen managed to capture all our attention with her eclectic and over-the-top fashion choices both on and off the screen. Colorful fur trim? Check. Endless bucket hats? Check. Crazy colorful animal prints? Of course. Raven helped pioneer Disney's more-is-more outlook on teen fashion.

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Now: Raven Symone

And coming full circle, Raven returned to her Disney roots a decade later in the That's So Raven reboot, Raven's Home, which premiered in the summer of 2017. The actress has stuck to her eccentric fashion choices on the new show and in real life on the red carpet.

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Then: Miley Cyrus

Miley Cyrus first burst onto the scene in 2006 as Hannah Montana. During her Disney days, she fully embraced the quintessential teen pop star look with plenty of tulle dresses, bubblegum pink, layered t-shirts, and many a denim skirt.

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Then: Miley Cyrus

Since leaving Disney, Miley has infamously gone through several out-there style transformations. But currently, she's settled upon more of a tamed-down, classic look mixed in with some of her signature southern roots.

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Then: Selena Gomez

At the start of Disney's Wizards of Waverly Place, Selena Gomez and BFF Demi Lovato went through the same slightly emo/punk-infused style phase. From Converse to studded belts and Avril Lavigne-inspired looks, the actress's off-screen style differed from the ultra-girly looks her character rocked on TV.

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Now: Selena Gomez

Today, Selena's look has become known for her sleek, feminine, and sexy style choices. With a Coach contract and countless magazine covers, she's more immersed in the fashion world now than ever before.

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Then: The Jonas Brothers

Inspiring screams from every teenage girl in the country, the Jonas Brothers (Nick, Kevin, and Joe) hit the scene with a skater-inspired, wannabe punk-rock sense of style in 2006. From band tees, to Converse, and yes, studded belts, the trio's look was full-on angsty teen meets boy-next-door.

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Now: The Jonas Brothers

A decade later, the boy band famously went their separate ways and came back together again with a brand new album in June 2019. Spearheading their comeback and grownup style transformation, Kevin, Nick, and Joe starred on the first-ever Men's BAZAAR.com cover to coincide with the debut of their new album. Leaving their angsty teen style behind, the brothers have all grown into their own sense of style full of suiting.

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Then: Demi Lovato

A fan of menswear-inspired pieces, layering, and an emo/punk-inspired aesthetic, Demi's early Disney style was a little more edgy than her BFF Selena Gomez's. Along with her sitcom, Sonny With A Chance, and Camp Rock movie alongside the Jonas brothers, Lovato also juggled her own singing career—which seemingly influenced her emo/rocker style further.

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Now: Demi Lovato

The singer's look has since matured and now, she tends to wear sexy, body-hugging pieces that show off her curves.

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Then: Ashley Tisdale

All hail the teenage QUEEN of bad early aughts fashion. Ashley Tisdale took notes from both Paris Hilton and Barbie herself with all her over-the-top pink fashun. Tisdale committed to her ultra-girly style persona both on-screen with her roles in High School Musical and The Suite Life of Zack and Cody and off-screen on the red carpet.

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Now: Ashley Tisdale

Tisdale has come a long way from her Disney style today. Now, the actress has found a more refined personal style, fusing together West Coast ease with East Coast glam.

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Then: Shia LaBeouf

From graphic t-shirts to ultra-baggy jeans, Shia LaBeouf's Disney days were cemented by his typical early 2000s teenage boy fashion.

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Now: Shia LaBeouf

Now a normcore style icon, Shia LaBeouf's aestheic has won over the Internet and hypebeasts alike. His penchant for military-inspired gear, ironic sweatshirts, and dad wear is a swift departure from his Disney days.

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Then: Vanessa Hudgens

During her High School Musical style era, Disney's It girl stuck to an ultra-girly uniform of ruffled dresses, lots of pink, and the graphic t-shirts that ruled the mid-2000s.

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Now: Vanessa Hudgens

Now, Hudgens has adopted the ultimate Californian girl wardrobe filled with ethereal sundresses, straw hats, and all the West Coast cool-girl-approved brands.

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Then: Zac Efron

Flip flops, tropical shirts y0ur dad used to wear, and faded jeans defined Zac Efron's style during his Disney years and High School Musical.

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Now: Zac Efron

Now, the actor's style has matured to classic suits and tuxedos in neutral colors on the red carpet.

Lauren Alexis Fisher is the Senior Editor at Cosmopolitan, overseeing digital content across fashion, lifestyle, beauty, sex, and culture. Previously, she was the Market Editor at Harper’s BAZAAR and has written for publications including WWD, Bustle, and W Magazine. When she’s not busy taste-testing her way through every dirty martini in New York, you can follow her on Instagram for bad jokes, good outfits, and annoying vacation pics. 

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