18 Outfits That Disney Stars Probably Regret Wearing

Whoever said that with age usually comes wisdom probably saw all these photos. We present nine of our favorite (and controversial) Disney stars and their humble yet highly amusing beginnings.

P.S. No Lindsay Lohan pictures here, though. We have to admit that the girl got too good too quickly.

1. Ashley Tisdale

Ashley Tisdale 1Ashley Tisdale at the launch party of Label Los Angeles held at Cinespace in Los Angeles on April 21, 2005

Looks like someone forgot to bring her dress and decided to snip off a piece of the red carpet. Ashley Tisdale wore a dress that looked like a makeshift piece of clothing wrapped around her and bound by two ribbons. Her shoes were kind of cute, though.

Ashley Tisdale 2Ashley Tisdale at the Giffoni Film Festival Awards dinner held at the Nickelodeon Studios in Hollywood, California, on May 1, 2005

We’re not really sure what this dress was trying to be. Did it want to be all-floral Grecian goddess-like, or did it want to take Ashley jogging? Don’t get us started on her choice of inner wear, too.

2. Amanda Bynes

Amanda Bynes at the premiere of "Rugrats"Amanda Bynes at the premiere of Rugrats in Los Angeles on June 11, 2000

Okay, so this was a pretty decent dress for a little kid, but wearing slippers on the red carpet is definitely a celebrity style no-no. And her blue eyeshadow didn’t really help.

Amanda BynesAmanda Bynes at the Newark premiere of Hairspray in New Jersey on June 18, 2007

A flapper dress gone wrong. Was this dress inspired by eyelashes?

3. Britney Spears

Britney Spears 1Britney Spears promoting her latest film Crossroads in Amsterdam, Netherlands, on March 19, 2002

We have no words for this. The entire look is so overwhelming that we’ll just crawl to a dark corner, curl up into a fetal position, and silently let our tears fall. Oh, and we checked the date of this photo — this was definitely before her mental breakdown.

Britney Spears 2Britney Spears at the red carpet of the MTV Music Video Awards in New York on September 9, 1999

This is a top and skirt/pants combo, actually, but we had to put it here anyway. It was too epic to be left out.

4. Christina Aguilera

Christina Aguilera 1Christina Aguilera at the 1999 MTV Music Video Awards in New York on September 9, 2009

Oh, Christina, our darling Christina. You should have let your manager know that you wanted to join the Cheetah Girls instead of going on a solo career. Fine, these are leopard spots. We know.

Christina Aguilera Crazy Hair

Christina Aguilera 2Christina Aguilera at the World Music Awards in Monte Carlo, Monaco, on February 5, 2001

The dress is pretty hot (butt and side boob baring, hello?), but we just had to introduce you to Christina’s pet snakes. Who knew animals were allowed on the red carpet? On a celebrity’s head at that.

5. Demi Lovato

Demi LovatoDemi Lovato at the Chevy Rocks the Future event at Walt Disney Studios in Burbank, California, on February 19, 2008

Was this during that children’s game where you put on as many clothes as you can wear and run around in a relay race? No? Okay.

Demi LovatoDemi Lovato at the world premiere of Camp Rock II: The Final Jam held at the Alice Tully Hall in New York on August 18, 2010

We don’t know what that thing is, but whatever it is, the stuffing’s coming out of its side.

6. Hilary Duff

HILARY DUFF on set of 'The Perfect Man' beingHilary Duff on the set of The Perfect Man around Brooklyn Heights, New York, on June 25, 2004

We don’t think Hilary can tell the difference between the length of a top and the length of a dress.


HAYLIE DUFF AND HILARY DUFF Red CarpetHilary Duff, posing with her older sister Haylie Katherine Duff, at the 2005 MTV Movie Awards held at The Shrine in Los Angeles, California, on April 6, 2005

Talk about looking like you’re good enough to eat! Do marshmallows and cotton candy come with this dress? Or maybe a unicorn.

7. Miley Cyrus

Miley CyrusMiley Cyrus signing copies of her new DVD for Hannah Montana: Behind the Spotlight at HMV on Oxford Street in London, England, on March 27, 2007

The look is actually not bad for this cutie little teenybopper, except that baby Miley forgot to change out of her previous outfit first before slipping into that shiny green dress.

Miley Cyrus Disney Outfit RegretMiley Cyrus and Tish Cyrus leaving the Cheesecake Factory where they had dinner in Pasadena, California on March 22, 2008

Miley’s face says it all – layering a plaid shirt over a ruffled skirt with neon details is everything we never wanted. Where do we not sign up?

8. Selena Gomez

Selena Gomez,

Selena Gomez,Selena Gomez at the Tinker Bell DVD and Blu-Ray premiere held at the Capitan Theater in Los Angeles on October 19, 2008

Selena Gomez, our resident good girl, actually had the whole tent-dress-and-ribbon look down pat, except that she chose a vomit-green color that brought sheer sadness to her complexion, not to mention that she paired the dress with feces-brown shoes. We see what you did there.

9. Vanessa Hudgens

VANESSA ANNE HUDGENSVanessa Hudgens at the screening of High School Musical held at the Walt Disney Studios Main Theatre in Burbank, California, on January 14, 2006

Ah, the humble beginnings of Vanessa’s iconic boho-chic look. We had no idea that it spawned from a boho-chic-meets-cowgirl-hooker look, though.

Vanessa Anne HudgensVanessa Hudgens at the UK film premiere of High School Musical held at The Empire in London, England, on September 10, 2006

This look totally reminds us of Christina Aguilera’s “Dirrty” days, except that Vanessa decided to go to the prom with it. Or maybe Baby V was channeling Christina’s epic wedding dress performance with Britney Spears and Madonna at the VMAs. If that’s the case, she totally nailed it.

Zac Efron and Vanessa Anne HudgensZac Efron and Vanessa Hudgens at the press event for High School Musical held at the Renaissance Hollywood Hotel in Los Angeles, California, on April 5, 2006

This dress actually isn’t all that bad if you consider Vanessa with all her teenage naiveté. We just felt like we needed to throw in some Zac Efron, not because we can but because we should.

Credit: Rachel Worth/Peter Piljman/Joshua Bucklan/Apega/Ivan Nikolov/HRC/Bryan Lamb/Billy Kirk/
Nikki Nelson/Vince Maher/Jody Cortes/WENN

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