15 Worst Hairstyles From 2000s Movies

Talk about a bad hair day.

The good, the bad, and the confusing of Y2K fashion are currently having a renaissance, but the early 2000s wasn’t just a time for experimental clothing — it was also an interesting time for hairstyles.

Some of the most iconic Y2K hairstyles have been immortalized in the media from that time period (i.e. the entire Lizzie McGuire series). However, not every hairstyle that made it to screen was…well, worthy of being brought back into the trend cycle.

Here are 15 hairstyles I can’t believe we let ’00s movies call fashion:


Polly’s awkwardly placed butterfly clips in Along Came Polly.

Universal / ©Universal/Courtesy Everett Collection

Butterfly clips are still cute, just not like this.


Jenna’s messy updo from 13 Going on 30.

Columbia Pictures / ©Columbia Pictures/Courtesy Everett Collection

I’m just confused as to how this ‘do was even achieved — is this what a banana clip is for?


Ian’s spiky hair from What a Girl Wants.

Warner Bros / ©Warner Bros/Courtesy Everett Collection

He’s perfect in every way except for his hair, which has so much gel in it that it glistens.


Shelby’s poorly executed Farrah Fawcett look from A Cinderella Story.

Warner Bros / ©Warner Bros/Courtesy Everett Collection

The amount of hairspray it took to achieve this look is responsible for 85% of the hole in the ozone layer.


Linda’s emo bangs from Be Cool.

Mgm / ©MGM/Courtesy Everett Collection

It seems like a safety hazard.


Ryan’s Pepto Bismol pink hat from High School Musical 2.

Disney Channel / ©Disney Channel/Courtesy Everett Collection

I stanned Ryan so much as a kid that I had the doll that wore this outfit, but looking back, this hat is just an atrocious shade of pink. Maybe it’s a good thing I lost the doll’s hat so quickly.


Galleria’s ring of Saturn hat from The Cheetah Girls 2, which has haunted me for years.

Disney / Via Disney+

This pointless hat ruined an otherwise spectacular look. The other Cheetah Girls got flowers in their hair during this scene. 

I think about this horrible hat at least once a day. 


Layla’s Princess Leia pigtails from Sky High.

Buena Vista Pictures / ©Buena Vista Pictures/Courtesy Everett Collection

Why didn’t they simply…finish putting her hair into buns?


Tibby’s chunky blue streaks and pulled-back bangs from The Sisterhood of the Traveling Pants.

Warner Bros / ©Warner Bros/Courtesy Everett Collection

And they’re fading to green…


Elle’s “flat in the front, volume in the back” look from Legally Blonde 2: Red, White, and Blonde.

Mgm / ©MGM/Courtesy Everett Collection

Maybe she permed the back then accidentally deactivated the ammonium thioglycolate.


Mimi’s pigtails and bandana from Crossroads.

Columbia Pictures / ©Columbia Pictures/Courtesy Everett Collection


Cesca’s sky-high pigtails from Spy Kids 3-D: Game Over.

Dimension Films / ©Dimension Films/Courtesy Everett Collection

Why’d they have to do Salma Hayek like that? She’s not 3 years old.


Troy’s stupid bandanna from High School Musical 3: Senior Year.

Walt Disney Co. / ©Walt Disney Co./Courtesy Everett Collection

It looks like he’s getting ready to compete in the Disney Channel games.


Anna’s chunky highlights in Freaky Friday.

Walt Disney Co. / ©Walt Disney Co./Courtesy Everett Collection

Growing up, I thought she looked so cool, but now, I’m pretty sure her stylist just did a few foils at the very top of poor Lindsay’s head and called it a day.


And finally, Aaron’s baby Bieber bangs from Mean Girls.

Paramount / ©Paramount/Courtesy Everett Collection

Regina was right — his hair looked way better pushed back.

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