The 22 most memorable dresses in romantic comedy history

Iconic movie dresses — Jennifer Garner in '13 Going on 30'; Kate Hudson in 'How to Lose a Guy in 10 Days'; Constance Wu in 'Crazy Rich Asians'. Photo:
Columbia/Everett; John Clifford/Paramount/Kobal/Shutterstock; Sanja Bucko/Warner Bros

Meet-cutes, earworm-filled soundtracks, charming leads... Myriad elements constitute the perfect rom-com, but nothing scratches the brain quite like a gasp-inducing fashion moment. Thanks to the attentive work of costume designers, every rom-com lover can instantly recall the moment Julia Roberts stepped out in that red gown in Pretty Woman (1990) or when Kate Hudson slipped into that yellow silk dress in How to Lose a Guy in 10 Days (2003). Since their onscreen debuts, these looks — whether chic or disastrous — have been referenced by celebs, used as costumes, and even showcased in museums.

Read below for EW's picks for the best rom-com dresses.

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How to Lose a Guy in 10 Days (2003)

HOW TO LOSE A GUY IN 10 DAYS, Kate Hudson, Matthew McConaughey, 2003, (c) Paramount/courtesy Everett — Kate Hudson and Matthew McConaughey in 'How to Lose a Guy in 10 Days'. Everett Collection

How-to girl Andie (Kate Hudson) might know how to lose a guy, but she also knows how to keep one: a drop-dead-gorgeous slinky yellow dress.

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Anyone but You (2023)

sydney sweeney ANYONE BUT YOU — Sydney Sweeney in 'Anyone but You'.
Brook Rushton/Sony Pictures

We can't blame Ben (Glen Powell) for falling head over heels! Beatrice's (Sydney Sweeney) pale blue silk gown — reminiscent of Andie's yellow slip in How to Lose a Guy in 10 Days — goes through a lot: a boat wedding, a plunge overboard, and a helicopter rescue. The rest is still unwritten.

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The Devil Wears Prada (2006)

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 (2008)

27 DRESSES, Katherine Heigl, 2008. TM &©20th Century Fox. All rights reserved/courtesy Everett Colle — Katherine Heigl in '27 Dresses'. Everett Collection

The most memorable of the 27? This Gone With the Wind (1938) nightmare.

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Last Holiday

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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Crazy Rich Asians (2018)

Rachel Chu (Constance Wu) earned the respect — or at least head turns — from her boyfriend's (Henry Golding) family when she wore this fabulous blue tulle dress at a boujee Singapore wedding. And as if it couldn't get any more iconic, the dress is now exhibited at the Smithsonian's National Museum of History.

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What a Girl Wants (2003)

WHAT A GIRL WANTS, Cassie Powney, Amanda Bynes, Connie Powney, 2003, (c) Warner Brothers/courtesy Ev — Amanda Bynes in 'What a Girl Wants'. Everett Collection

Peak 2000s teen girl feels: seeing Amanda Bynes at the top of the stairs in the dress she designed by altering the hideous one she was given.

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She's All That (1999)

She's All That Rachel Leigh Cook — Rachael Leigh Cook in 'She's All That'.
Miramax

How could we possibly leave out Laney's (Rachael Leigh Cook) little red dress in one of the most classic makeover reveals in rom-com history?

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The Decoy Bride (2011)

THE DECOY BRIDE, Kelly Macdonald, 2011. ph: Nick Wall/©IFC Films/Courtesy Everett Collection — Kelly Macdonald in 'The Decoy Bride'. 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 (1998)

Drew Barrymore in 'Ever After'. 20th Century-Fox/Photofest

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

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A Cinderella Story (2004)

A CINDERELLA STORY, Hilary Duff, 2004, (c) Warner Brothers/courtesy Everett Collection — Hilary Duff in 'A Cinderella Story'. Everett Collection

Another Cinderella story, another perfect entrance.

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Sixteen Candles (1984)

In one of the most instantly recognizable shots in cinema, Sam (Molly Ringwald) wears her iconic lilac bridesmaid dress and floral headpiece as she sits across from her crush (Michael Schoeffling) and the birthday cake he brought for her. (No surprise Ariana Grande recreated this moment in her music video for "We Can't Be Friends (Wait for Your Love).")

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Enchanted (2007)

ENCHANTED, Amy Adams, 2007. ©Buena Vista Pictures/courtesy Everett Collection — Amy Adams in 'Enchanted'. Everett Collection

Giselle's fluffy white gown may have been memorable, but Amy Adams owns the color purple during the movie's climax.

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Clueless (1995)

CLUELESS, Justin Walker, Alicia Silverstone, 1995, (c) Paramount/courtesy Everett Collection — Justin Walker and Alicia Silverstone in 'Clueless'. Everett Collection

Cher (Alicia Silverstone): "It's a dress!"

Mel Horowitz (Dan Hedaya): "Says who?"

Cher: "Calvin Klein!"

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

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Pretty Woman (1990)

Julia Roberts in 'Pretty Woman'. Everett Collection

Just missing a diamond necklace worth more than most annual incomes.

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Legally Blonde (2001)

Elle Woods (Reese Witherspoon) won a homicide trial and taught everyone the "first cardinal rule of perm maintenance" — all while slaying a pink belted pencil dress.

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Bridesmaids (2011)

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

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Never Been Kissed (1999)

NEVER BEEN KISSED, Drew Barrymore, 1999. — Drew Barrymore in 'Never Been Kissed'. Everett Collection

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

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10 Things I Hate About You (1999)

10 THINGS I HATE ABOUT YOU, from left: Larry Miller, Larisa Oleynik, Joseph Gordon-Levitt, 1999, © B — Laria Oleynik in '10 Things I Hate About You'. Everett Collection

Imagine having the guts to wear separates to your prom! Separates! Bianca (Larisa Oleynik) is iconic.

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13 Going on 30 (2004)

13 GOING ON 30, Andy Serkis, Jennifer Garner, 2004, (c) Columbia/courtesy Everett Collection — Jennifer Garner in '13 Going on 30'. Everett Collection

Admit it: You wanted to learn the dance to Michael Jackson's "Thriller" after this scene.

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To All the Boys I've Loved Before: P.S. I Still Love You (2018)

To All the Boys I Loved Before: P.S. I Still love you — Lana Candor in 'To All the Boys I Loved Before: P.S. I Still Love You'.
Netflix

Lara Jean (Lana Condor) gets her fairy-tale moment, exchanging "I love yous" with Peter Kavinsky (Noah Centineo) while twirling in a turquoise '50s-style tulle gown...in the snow!

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