29 Bad 2000s Movie Outfits

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“Whoever said orange was the new pink was seriously disturbed.” —Elle Woods

The early 2000s was a golden age for rom-coms and teen movies.

However, looking back from the 2020s, I can’t imagine ever thinking some of their most iconic style moments were, well, actually stylish.

So, here are 29 outfits I can’t believe we let ’00s movies call fashion:


Gabriella’s wilted flower prom dress from High School Musical 3: Senior Year.

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

This must be where Vanessa Hudgens’s love of Coachella fashion began.


Jennifer’s Limited Too jacket from Jennifer’s Body.

20thcentfox / ©20thCentFox/Courtesy Everett Collection

I know this outfit is iconic, but hear me out — it looks like something a fourth grader would pick out.


Aquamarine’s aquamarine dress from Aquamarine.

20thcentfox / ©20thCentFox/Courtesy Everett Collection

It’s like if Pink wore pink.


Anna’s baggy “I’m in a band” pants from Freaky Friday.

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

She looks like she’s rebelling against the Target employee dress code.


Galleria’s Christmassy vacation ‘fit from Cheetah Girls 2: When In Spain.

Disney Channel / ©Disney Channel/Courtesy Everett Collection

They should’ve let fashion icon Raven pick out her own outfits. She would’ve done a much better job.


Melanie’s all-denim getup from Sweet Home Alabama.

Buena Vista Pictures / courtesy Everett Collection

It’s giving…Britney and Justin.


Shelley’s halter top from The House Bunny, which appears to be one top sewed over another.

Columbia Pictures / ©Columbia Pictures/Courtesy Everett Collection

I would not trust this lady to give me a makeover.


Elle’s Slytherin professor outfit in Legally Blonde

MGM Distribution Co. / Via youtube.com

Emerald green is not the new pink, and she’s obviously a Ravenclaw anyway.


Mia’s underwhelming ball gown from the end of The Princess Diaries

Buena Vista Pictures / Via disneyplus.com

Yes, she looked *stunning*; but on its own, the dress looks like it was made out of curtains.


Andy’s attempt at fitting in at Runway in The Devil Wears Prada

20th Century Fox / Via youtube.com

I’m pretty sure the jacket was commissioned from the Cheetah Girls by the Queen of England. The giraffe purse certainly isn’t doing it any favors.


Penny’s doily-ish crop top from Almost Famous.

Dreamworks / ©DreamWorks/courtesy Everett / Everett Collection

It looks like she cut the lace hem off another shirt and added straps.


Big’s basic button-down in Sex and the City

Warner Bros. Pictures / Via youtube.com

He really proposed to fashion icon Carrie Bradshaw wearing the single most boring piece of clothing he could find in his closet.


Kenya’s first date outfit in Something New

Focus Features / Via youtube.com

It’s the matching shirt and sweater set for me.


Jenna’s ’80s-inspired party look in 13 Going on 30

Sony Pictures Releasing / Via youtube.com

Don’t get me wrong, this look is iconic. But there’s…a whole lot going on.


Daphne’s casual couture that she wore on the runway in What a Girl Wants

Warner Bros. Pictures / Via Netflix

It was cute enough for, like, a run to the store, but it was far too basic for the runway. TBH, I’d expect more from the girl who transformed a hideous dress into an absolutely stunning gown with a pair of craft scissors.


Juliet’s train conductor hat from Love Actually

Universal Pictures / Via youtube.com

Is this Love Actually or The Polar Express? Somebody needs to let her know.


Lucinda’s Dollar Tree fairy outfit from Ella Enchanted

Miramax / ©Miramax/Courtesy Everett Collection


Bella’s first day of school pajamas in Twilight

Summit Entertainment / Via youtube.com

I said what I said. Her shirt looks like a cross between pajamas and scrubs with a long-sleeved shirt underneath for warmth.


Hitch’s blazer/shirt combo in Hitch

Sony Pictures Releasing / Via youtube.com

It’s the pin-striped shirt for me. It would be better with a solid color shirt underneath, I think.


Giselle’s modern dress in Enchanted

Walt Disney Studios Motion Pictures / Via youtube.com

It’s just so plain compared to all the outfits she makes herself. No wonder she opens up her own fashion business at the end of the movie. New York needed her!


Regina’s “professional in pink” ensemble from Mean Girls

Paramount Pictures / Via youtube.com

If I was attending a new high school and saw someone wearing this, I’d assume they were a brand-new teacher, not the most popular girl in my class. I guess businesswear suits her, though, since she was the boss.


Steve’s very boring sweater in The Wedding Planner

Sony Pictures Releasing / Via youtube.com

Jennifer Lopez serves so many AMAZING looks in this movie that there must not have been enough left in the budget to provide Matthew McConaughey with anything interesting to wear.


Summer’s wrinkly dress in 500 Days of Summer

Fox Searchlight Pictures / Via youtube.com

It practically blends in with the copy machine.


Andie’s splotchy, polka-dot dress in How to Lose a Guy in 10 Days

Paramount Pictures / Via youtube.com

It’s a watercolor effect gone wrong. I think a different color palette could’ve saved the design.


Jules’s clubbing outfit in Bend It Like Beckham

Helkon SK / Via youtube.com

No matter how much I try, I will never understand this top. Is the bottom centimeter tucked in? Is it a bodysuit? Is it folded and pinned into a triangle?


Sophie’s summer camp shorts in Mamma Mia!

Universal Pictures / Via youtube.com

The shirt is alright, but it looks weird with the shorts. Like, this should be two different outfits.


Sarah’s giant tiger necklace in Forgetting Sarah Marshall

Universal Pictures / Via youtube.com

I have so many questions about this wardrobe choice. Why a tiger? Why is it so big? How heavy is it? Did it give Kristen Bell permanent neck pain?


Viola’s seatbelt-inspired dress in She’s the Man

Paramount Pictures / Via youtube.com

It kind of looks like she turned a tote bag into a dress, not gonna lie.


And finally, Elle’s Jackie Kennedy outfit from Legally Blonde 2: Red, White, and Blonde.

Mgm / ©MGM/Courtesy Everett Collection

The gloves ruin  it for me.