It’s almost Valentine’s Day, which means that it is time to rewatch all of the classic romantic comedies. You’ll wrap yourself in a blanket, pour some Kahlua into some hot chocolate, and get ready to cry over that moment in You’ve Got Mail when she says, “I hoped it was you” and all of the expositional rivalry is forgotten. Or something like that.
If you’ve watched enough rom coms, which I certainly have, you’ll find that there are iconic clichés and graceless tropes that are common throughout the genre. Rom coms aren’t really known for being original, and in some of the lower budget Hallmark ones, it’ll be like a Frankenstein-ing of the classic platitudes stolen from the corpses of better scripts. I’m a sucker for a good archetype, and it’s interesting how different movies will beat one to death in an entirely new way.
I like putting together outfits with a story. If you choose well enough, it can feel like you’re stepping into another story or being another character for the day. All of these outfits below come with their own rom com subplot.
The Woman Who Is Clearly About to Get a Makeover
You’ll know her as soon as she appears on screen. She’s stunning, but she’s been hidden under a thick layer of loose fitting clothes and geeky glasses. In order to find love/success/happiness she must endure a metamorphosis. We can’t see her personality with those glasses in the way! In about half an hour, she’ll remove her spectacles, discover the joys of well-fitting jeans, and flawlessly apply winged eyeliner even though it’s been made clear that she has never indulged in makeup before. Soon she will be beautiful enough to catch the eyes of our hero! But for now, she’s carrying books and acting as if she has never spoken to a human before. She’s wearing flat shoes. Flat shoes. But don’t worry, she’s amazingly beautiful as soon as she takes off the glasses. She won’t be able to see street signs or read the allergy warnings on restaurant menus anymore, but at least she’s beautiful now!
As seen in: Gracie in Miss Congeniality, Mia Thermopolis in The Princess Diaries, Allison in The Breakfast Club, Toula in My Big Fat Greek Wedding, Sandy in Grease, Andy in The Devil Wears Prada, Cady in Mean Girls, Tai in Clueless, Josie in Never Been Kissed, almost everyone in The House Bunny (I’ve never worked up the stomach to finish this whole movie, so correct me if I’m wrong and the Zeta Alpha Zeta girls discover that the real beauty was inside them all along after getting their extreme makeover), and possibly the ancestor of this trope… Eliza Doolittle in My Fair Lady.
Get the look: Wear glasses, flat shoes, ill-fitting clothing, and don’t brush your hair. Make sure to be obviously uncomfortable in your own skin because we all know that women can’t be confident and self-assured unless they look bomb.
The Brisk and Calloused Journalist Who Must Be Taught to Love
She’s a career woman. She’s smart. She’s a pragmatic cynic. And worst of all, she doesn’t prioritize romance! She’s obsessed with her job and is no fun at all. Her male counterpart will be fixated on teaching her how to have fun, be spontaneous, let loose, but for now, she wears mostly black and is kind of mean. She just needs the right man to teach her about balance! Once she finds love, she’ll abandon her high paying job that gives her financial freedom and a sense of fulfillment. Ah, romance!
As seen in: Sarah in Hitch, Miranda Priestly in The Devil Wears Prada, Miranda in Sex and The City, Amy in Trainwreck, Margaret in The Proposal. See Kevin in 27 Dresses for the Male Version.
Get the look: All black. Stilettos or very loud boots so you will always be heard when you walk. Carry a newspaper because in this story, the decline of print media never occurred.
The Naïve and Pure Teen Who Is Also Very Sexy
This look is lifted almost entirely from Bianca’s style in 10 Things I Hate About You. This character is gentle, sweet, kind. She wants to be popular and she usually is. Everyone is in love with her. She might be smart, clever, mean, or stupid, but we don’t care about that. All we care about is that she is pretty and generally wearing pastels. Boys she doesn’t even know will defend her purity! She is the embodiment of male fantasy. She is very, very sexy and probably DTF but she is also pure and precious so that when the male protagonist finally gets the girl, he is the first to drive his flag into the sand. As Edward Dahlberg once said, “what men most desire is a virgin who is a whore.” This character perfectly encapsulates that idea. She’s just an idealized figment of male desire. She’s not really imagined as a whole person but look at how cute she is!
As seen in: Bianca in 10 Things I Hate About You
Get the look: Wear a floral print sundress. The exposed shoulder and collar bone will just drive him crazy, but the soft pastel palette will prove that you’re still pure! A short necklace will draw eyes to your barely revealed décolletage. Maybe it has a daisy on it. Flowers represent purity. And also vaginas.
The Angry Feminist Who Is Still Very Sexy
This look is the counterpart to our naïve and pure teen. To perfectly capture the dichotomy of the two types of women in the world, choose a friend to dress up as the very sexy teen!
This character is an example of how feminists are bad! They hate men and they are sometimes very sexy to the male characters because they know they can never have her since she hates men! She reads books and quotes Sylvia Plath. She doesn’t wear a lot of makeup because she subscribes to the surface level feminism that assumes anyone who wears makeup is objectifying themselves. Luckily, she is stunning without it. She’s mean to the men around her in a way that makes them mad and also turns them on. Her sassy comments have too many big words. How does she say them so fast? Does she practice? This look embodies my whole high school vibe and adds a splash of sexiness. Is she an oversimplification of feminist theory? Maybe. But is she pretty damn sexy? Hell yes.
As seen in: Kat in 10 Things I Hate About You.
Get the look: Wear loose pants and ugly sandals. Put your hair up and don’t wear accessories. Beauty is for the asinine, you’re too smart to bother with your appearance. Don’t wear a bra. Angry feminists always burn their bras and also it will give the male viewers a tantalizing look at some nipple bumpage. Note that this step is entirely unattainable for those larger than a B-cup and may need a bralette to serve as a substitution for going braless.
The Best Friend Who is a Mess
She’s a disaster. She doesn’t really care about her job and she is often drunk. She’s kind of mean and she’s gasp a casual dater! She gives terrible advice and her very existence makes our protagonist look better as a person. She’s sloppy, sexually avaricious, perhaps foul mouthed and 100% comfortable in her own skin. She has no qualms about showing up to work wearing half of her bridesmaid outfit and a button down shirt she stole from her latest conquest. She is a foil to our protagonist, usually situated in a way to make the leading lady’s quest for unending love look more noble. She can’t really get her life together and she doesn’t really care. She provides the sassy comments, the horrible suggestions, the comic relief, and most importantly, the wine.
As seen in: Judy Greer as Casey in 27 Dresses, Judy Greer as Lucy in 13 Going on 30, Judy Greer as Penny in The Wedding Planner, Judy Greer being criminally underused in every movie she’s ever been in. Give me more Judy Greer!
Get the look: Make sure your look uses only slight tweaks to make your night out/wedding reception/engagement party look daytime appropriate. Smudge and blend your slept-in smokey eye to look less like a raccoon, comb your hair with your fingers, and use your bridesmaid sash as a stylish belt for the shirt you stole from your groomsman. Bring that half empty bottle of wine because hey, the party doesn’t stop!
We are coming into a new age of rom coms. Ladies are heading the writer’s rooms, LGBTQ+ characters are finally appearing as more than a stereotype, and the romantic interest doesn’t always have to be a mediocre looking white man who needs to learn how to iron. With this age of new, diverse directors, writers, and producers hopefully we will come to an age where our tales of romance don’t lean so heavily on stereotypes and oversimplifications. Until then, I’m going to give all of my outfits a secret rom com subplot because I love a happy ending.
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