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  1. Home
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  3. 16 of the most iconic dresses in romantic-comedy history

16 of the most iconic dresses in romantic-comedy history

By Dana Schwartz April 25, 2018 at 07:48 PM EDT
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How to Lose a Guy in 10 Days

HOW TO LOSE A GUY IN 10 DAYS, Kate Hudson, Matthew McConaughey, 2003, (c) Paramount/courtesy Everett
Credit: Everett Collection

How-to girl Andie might know how to lose a guy, but she also knows how to keep one: a drop-dead-gorgeous slinky yellow dress. Who but Kate Hudson could pull off that color?

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The Devil Wears Prada

The Devil Wears Prada - 2006
Credit: Barry Wetcher/20th Century Fox/Kobal/REX/Shutterstock

It's more than worth missing your boyfriend's birthday party if you get an excuse to wear that perfect black gown.

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27 Dresses

27 DRESSES, Katherine Heigl, 2008. TM &©20th Century Fox. All rights reserved/courtesy Everett Colle
Credit: Everett Collection

The most memorable of the 27? This Gone With the Wind nightmare.

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Last Holiday

The Last Holiday
Credit: Stephen Vaughan/Paramount

Queen Latifah lives up to her name and looks every bit a royal in the custom gown her character has made when she thinks she only has weeks left to live.

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What a Girl Wants

WHAT A GIRL WANTS, Cassie Powney, Amanda Bynes, Connie Powney, 2003, (c) Warner Brothers/courtesy Ev
Credit: Everett Collection

Peak ’00s teen girl feels: seeing Amanda Bynes at the top of the stairs in the dress that she designed herself by cutting away the hideous one she was given.

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The Decoy Bride

THE DECOY BRIDE, Kelly Macdonald, 2011. ph: Nick Wall/©IFC Films/Courtesy Everett Collection
Credit: Everett Collection

The Decoy Bride is a cheesy Netflix hidden gem, with gorgeous Scottish countryside and dresses to swoon over.

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Ever After

EverAfter_Barrymore.JPG
Credit: 20th Century-Fox/Photofest

How could you not get chills when Danielle (Drew Barrymore) shows up to the ball? Da Vinci was her fairy godmother — er, father!

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A Cinderella Story

A CINDERELLA STORY, Hilary Duff, 2004, (c) Warner Brothers/courtesy Everett Collection
Credit: Everett Collection

Another Cinderella story, another perfect entrance.

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Enchanted

ENCHANTED, Amy Adams, 2007. ©Buena Vista Pictures/courtesy Everett Collection
Credit: Everett Collection

Giselle's fluffy white gown may have been memorable, but Amy Adams looks unfairly gorgeous in purple during the movie's climax.

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Clueless

CLUELESS, Justin Walker, Alicia Silverstone, 1995, (c) Paramount/courtesy Everett Collection
Credit: Everett Collection

"It's a dress!"

"Says who?"

"Calvin Klein!"

Thank goondess that, unlike her Alaia, this white dress doesn't end up against the street.

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Pretty Woman

PRETTY WOMAN, Richard Gere, Julia Roberts, 1990
Credit: Everett Collection

Just missing a diamond worth more than I make in a year.

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Bridesmaids

BRIDESMAIDS (2011) Maya Rudolph (screen grab) CR: Universal Pictures
Credit: Universal Pictures

This isn't the dress that Lillian ended up wearing to her wedding. Probably for the best.

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Never Been Kissed

NEVER BEEN KISSED, Drew Barrymore, 1999.
Credit: Everett Collection

Poor Josie Grossy — not even Drew Barrymore can pull off shiny pink.

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10 Things I Hate About You

10 THINGS I HATE ABOUT YOU, from left: Larry Miller, Larisa Oleynik, Joseph Gordon-Levitt, 1999, © B
Credit: Everett Collection

Imagine having the guts to wear separates to your prom! Separates! Bianca is iconic.

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13 Going on 30

13 GOING ON 30, Andy Serkis, Jennifer Garner, 2004, (c) Columbia/courtesy Everett Collection
Credit: Everett Collection

Admit it: You wanted to learn the dance to "Thriller" after this scene.

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Girls Trip

2481_FPF_00060R.JPG
Credit: Universal Pictures

"This dress is a mosquito net."

"Then maybe you'll actually catch something in it."

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    1 of 16 How to Lose a Guy in 10 Days
    2 of 16 The Devil Wears Prada
    3 of 16 27 Dresses
    4 of 16 Last Holiday
    5 of 16 What a Girl Wants
    6 of 16 The Decoy Bride
    7 of 16 Ever After
    8 of 16 A Cinderella Story
    9 of 16 Enchanted
    10 of 16 Clueless
    11 of 16 Pretty Woman
    12 of 16 Bridesmaids
    13 of 16 Never Been Kissed
    14 of 16 10 Things I Hate About You
    15 of 16 13 Going on 30
    16 of 16 Girls Trip

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