Lessons in Style and Seduction from Cruel Intentions

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Cruel Intentions (1999)

As New York Fashion Week gets underway, we look to the 1999 classic and its teen tyrants for tips on navigating Manhattan with style

1999’s Cruel Intentions, an updated take on Choderlos de Laclos’ 1782 novel Les Liaisons Dangereuses, proved something that teenagers already knew: if there’s anyone more preoccupied with social standing than 18th century French aristocrats, it’s New York City high schoolers. Set in the privileged world of Manhattan private school kids, the film follows Machiavellian Kathryn Merteuil. Freshly dumped, Kathryn teams up with her stepbrother, Sebastian, in order to get back at her former paramour. Whoever said revenge was a dish best served cold clearly didn’t know these guys. For them, retribution looks steamy as hell. Sebastian agrees to de-virgin Cecile, the innocent young girl Kathryn’s ex left her for. Complaining that the task is too easy, the scheming siblings make another wager. If Sebastian is able to seduce Annette, their headmaster’s virtuous daughter, he gets to bed Kathryn. If he fails, she gets his vintage Jag. Sporting Prada polo necks and baroque-inspired lingerie, the pair mount their campaign, spinning a web of deceit around the city with their trademark elegance and wit.

1. Don’t be afraid to add Rococo flair
Though the world Kathryn and Sebastian inhabit is the modern Upper East Side, their wardrobes make subtle nods to the film’s original source material. Favouring lace or a burnt orange bustier, Kathryn uses clothing to seduce the men around her into compliance. Meanwhile Sebastian, a libertine-in-training, strolls around the city in a long fitted tailcoat. Perfect for making a dramatic exit.

2. For a colourful life, wear black
Kathryn and Sebastian’s ensembles often abandon colour and focus instead on cutting a striking silhouette. When Kathryn takes Cecile for a Central Park picnic, the outfits of the two girls function metaphorically. Cecile, in her preppy pastels, is innocence personified, while Kathryn’s slick black skirt suit and statement sunglasses suggest a woman who’s seen much of the world, and is ready to take charge.

3. Perfect that pout
If there’s one principle these siblings stick to, it’s that while you’re paying lip service, your lips better look good. Kathryn opts for a brown-toned lipstick when doling out falsehoods to concerned Upper East Side parents. Sebastian has a pucker that’s riper than a summer strawberry and he employs it to good, brooding use in his seduction of Annette.

4. Make it multi-task
We’re not advising you use your necklace to store class As, but you have to admire Kathryn’s sneaky efficiency when it comes to that infamous crucifix. Try channeling her resourcefulness with beauty products that work double time, or functional accessories that look cute and serve a purpose.

5. Give women control over their own bodies
At the root of Kathryn’s malice is fury at society’s hypocritical attitudes towards sex. “I’m the Marcia-fucking-Brady of the Upper East Side,” she complains, “and sometimes I want to kill myself”. It’s said with so much bitterness that you forget Kathryn’s played by the same actress who, as Buffy, has saved the world from multiple apocalypses. Had Kathryn been living in a community willing to accommodate her appetites, some hearts could have surely been saved.

Even Annette, who has some stereotypically conservative views on sex, seems to find herself through the very act that she openly disavowed at the film’s beginning. Neither of these women feel they have permission to be themselves, and there’s a high price to pay for their conformity. Though the ending of Cruel Intentions does slip into a bit of moralising, the real message of the story is one worth remembering, particularly in the present political climate: Hell hath no fury like a smart woman scorned, especially when she’s wearing a Dolce & Gabbana power suit.