7 most iconic rom com outfits

“Oops. You know, you really should be more careful with silk.”
Never Been Kissed prom scene

Rom coms are easy watches that never tell us anything interesting about love. Boy meets girl, boy messes up, girl reunites with boy on the Brooklyn Bridge during a monsoon (eye make-up remains suspiciously intact). The formula is tried and tested. Luckily, there is one aspect of the modern romantic comedy which keeps us watching and which brings us back again and again to the heroines we love in spite of their flaws: the fashion.


You might not remember why Laney Boggs ultimately decides to give Freddie Prinze Jr. another chance in She’s All That (I dunno, something about fairy lights, a pool and his decision to go naked to their graduation ceremony), but I bet you remember what she wore to prom (a timeless sequined black slip number). It’s ingrained into our minds as much as Josie Grossie’s terrible white feathered cardigan in Never Been Kissed, or the gold heart shaped necklace an amoral Alan Rickman gives to his harlot secretary in Love, Actually.

It’s the sartorial choices that make these films iconic, which in turn constitute the real love stories for us. Not convinced? Then take a look through this hall of fame.

1. Laney Boggs’s makeover red dress
The scene in She’s All That when Laney Boggs descends her stairs to a song by Sixpence None The Richer as a seriously lovestruck Freddie Prinze Junior watches on, is so iconic its been lampooned in every teen movie parody since 1999. Who knew all it took was a trim and some light eyebrow care from a pre- True Blood Anna Paquin to transform this ugly duckling into a beautiful minimalist swan!

Later, Laney wears her beautiful crimson dress to a party where the school’s mean girl dumps rum and coke on her and advises “Oops! You know, you really should be more careful with silk!” What a bitch, but also, she’s kind of right?

2. Josie Grossie’s prom monstrosity
As a journalist who was also a total fucking neek at school, there is no scene to my mind more nightmarish in cinema history than Drew Barrymore’s traumatic prom flashback in the vastly underrated romantic comedy, Never Been Kissed. Clad in a millennial pink, prairie girl, latex nightmare dress that looks suspiciously like the kind of thing you’d expect Nasty Gal and Boohoo to be hawking to Insta baddies just in time for Boomtown, Josie (Grossie) is the victim of a vicious prank when the school fitty asks her to prom, only to pelt her with eggs.


As she sobs on her doorstep, he yells “Write a poem about this, nerd!” -- an insult that, on Josie’s behalf, cut me to my very core. But hey, Drew got the last laugh. Years later she returned to high school for her undercover report, getting the guy and accumulating a series of enviable cropped cardigans along the way. Also her prom outfit was in retrospect quite stylish. Very Vampire’s Wife. Very Reformation.


3. Kiera Knightley’s winter wedding lewk
It’s hard to get married in winter. Like, yes, it’s probably thousands cheaper and the guest list will be better because none of your friends will be on their holidays, but also it’s cold. Especially in London. Way too cold to wear the off-the-shoulder Vera Wang summer look you’ve been dreaming of. What to do!

Well, if you’re Kiera Knightley in Love, Actually (who probably has a character name but let’s be honest, she’s just Kiera Knightley in Love, Actually to us all), the answer is a simple one: Simply throw a white cardi on over the top. Perhaps with a fun trim? A feathered collar? Frame it with some carefully curled tendrils cascading from a loose bun and there you have it, the perfect noughties bridal attire. The practicality! Ugh, we love it.


4. Elle Woods’ Halloween costume
In 2019, where everything is very post-woke, Playboy has attempted to rebrand itself. It’s all about female empowerment and less about objectification and making bunnies parade around Hugh Hefner’s (GBNF) mansion these days, over at Playboy. But back in 2001, before the world was woke and lads mags were in such dire straits that they had begun resorting to these painfully transparent and cynical marketing tactics, the Playboy bunny had very different connotations.


Long derided by “serious women”, such as Legally Blonde’s prim vehicle for internal misogyny Vivian, played by Selma Blair, the bunny was in desperate need of reclamation. Enter Elle Woods. Tricked into believing a Harvard Halloween party was a costume event, she shows up in head to toe pink, in all her bunny glory. Her confidence shines through though, which lends the outfit immediate legitimacy. Let’s be honest, Reese Witherspoon’s Halloween costume walked so that Karen from Mean Girls’ mouse look could run.


5. Julia Roberts’ polka dots at the polo
Julia Roberts’s brown polka dot outfit, which she wears to masquerade as Richard Gere’s respectable date for a polo match in Pretty Woman, has become so iconic that it even inspired a Meghan Markle copy at a recent royal event. Obviously the British Royal Family are all complete fascists, but it’s a nice outfit so we can let this slide.

Coming close second: Julia’s far edgier blue and white cut-out dress, which she wears while still carrying out sex work, accessorised with a blonde bob. Hope Kate Middleton tries this one out soon.

6. Jenna Rink’s "Thriller" outfit
“Nice dress,'' says Jenna’s pre-teen neighbour as they ride in the lift together in the seminal 2004 classic, 13 Going on 30. “Thanks,” Jenna chirps back, grabbing her tits. “It’s because I’ve got these great boobs to fill it out!” Honestly, have any of us ever responded to a compliment with such refreshing honesty? Probably not.


The last time someone complimented you on a dress you were wearing you probably laughed awkwardly, or brushed it off, or said something stupid like “Thanks, it has pockets!” Adulthood has worn us down, pushed us to make ourselves smaller and dismissive of ourselves and our great sartorial choices and our bodies. We should embrace Jenna’s childlike enthusiasm for her fashion and herself. Later, Jenna takes her rainbow striped dress to the club, where it proves that it’s practical as well as stylish and boob-enhancing, enabling her to lead the entire party in a very of-its-time rendition of Michael Jackson’s 'Thriller'.


7. Josh’s plaid shirt in Clueless
“Oh okay, finally, a Clueless entry,” you may be thinking. “Well, obviously the most iconic outfit in Clueless is Cher Horowitz’s yellow plaid two piece!” Well, you are wrong. The most iconic outfit in Clueless is the plaid shirt (any plaid shirt) worn by Paul Rudd, who plays Cher’s step-brother and love interest, Josh.

Understated but nonetheless imbued with a potent sadboi sexual energy, the plaid is transformed from the everyday to the almost supernaturally sexy by Paul Rudd. Worn over slogan t-shirts as he play-fights with Cher on the sofa? Into it. The mustard check he wears while he undertakes voluntary legal work for Cher’s dad, and suddenly realises he’s hopelessly in love with her? Tattoo it directly onto my retinas. Layered under an all-black outfit and sunglasses while he lounges by the pool reading Nietzche? Fuck me UP, Paul Rudd. Basically, tartan has never been the same since this movie came out.

Normally this is where you’re supposed to say something like “Did we miss anything? Let us know in the comments!” But I will not be saying that because all of my choices are correct. Thank you and goodbye.

This article originally appeared on i-D UK.