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


MGM Distribution Co. / Via giphy.com

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


Paramount Pictures / Via giphy.com

So, here are 19 outfits I can’t believe we let ’00s movies call fashion.

19.

Elle’s Slytherin professor outfit in Legally Blonde

Snake-colored, shiny suit and plaid tie


MGM Distribution Co. / Via youtube.com

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

18.

Steve’s very boring sweater in The Wedding Planner

Simple sweater and ugly glasses


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.

17.

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.

16.

Juliet’s train conductor hat from Love Actually

A hat with a flap and a long denim coat


Universal Pictures / Via youtube.com

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

15.

Hitch’s tan blazer in Hitch

A basic brown blazer over a pinstripe shirt


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.

14.

Bella’s first day of school pajamas in Twilight

An ill-fitting button-down over long sleeves


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.

13.

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

Business attire with a shirt in Regina's trademark color


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.

12.

Giselle’s modern dress in Enchanted

A mermaid gown with no sparkles other than the rhinestones on the straps


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!

11.

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

Oversize, jewel tone coat lined with cheetah fur


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.

10.

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

A very basic shirt he probably wore to wore three days a week


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.

9.

Sophie’s summer camp shorts in Mamma Mia!

Peasant top and weird shorts


Universal Pictures / Via youtube.com

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

8.

Summer’s wrinkly dress in 500 Days of Summer


Fox Searchlight Pictures / Via youtube.com

It practically blends in with the copy machine.

7.

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

A dress with ruching on the waist and neckline and watercolor dots


Paramount Pictures / Via youtube.com

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

6.

Kenya’s first date outfit in Something New


Focus Features / Via youtube.com

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

5.

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.

4.

Jules’s clubbing outfit in Bend It Like Beckham

A high-cut bodysuit and low-rise jeans


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?

3.

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

Tight dress with straps connected by buckles


Paramount Pictures / Via youtube.com

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

2.

Sarah’s giant tiger necklace in Forgetting Sarah Marshall

A giant, shiny tiger pendant and a palm tree–print dress


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?

1.

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

Psychedelic minidress


Sony Pictures Releasing / Via youtube.com

Don’t get me wrong, this look is iconic. But there’s…a whole lot going on. I can’t believe the giant butterfly necklace was picked out by such a high-profile fashion magazine editor.

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CAESAR

THERE IS A TIDE IN THE AFFAIRS OF MEN..
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