Cruel Intentions Is Still a Teenage Fashion Dream 20 Years On

Janelle Okwodu
The film returns to theaters this week and brings with it a wealth of style inspiration.

Of all the fashionable ’90s teen movies, Cruel Intentions is arguably the chicest. Sure, Cher Horowitz had an amazing closet, but how many people can really wear yellow plaid with thigh-high stockings in real life? With its urbane perspective on youth culture, the film offered a counterpoint to the frothy Cluess fantasy at the time and returns to theaters this weekend for a 20th anniversary celebratory run. Its characters may have been worried about college applications and standardized tests, but they hid those concerns beneath layers of discreetly chic Prada.

A teen retelling of Les Liaisons Dangereuses, the story hinges on the same combination of lust and betrayal that made Pierre Choderlos de Laclos’s 1782 novel so potent. While the original satirized the treachery of French aristocracy during the Ancien Régime, its ’90s counterpart tackles the insular world of Manhattan’s prep schools and Upper East Side. Step-siblings and occasional paramours Kathryn Merteuil (a brunette Sarah Michelle Gellar) and Sebastian Valmont (Ryan Phillipe at his poutiest) turn romance into a sport, hoping to entrap their fellow students and one up each other. Unscrupulous and conniving, Sebastian and Kathryn would be well suited for each other if their parents weren’t married. They both employ beauty and style as a weapon, scheming and taking bets on whether or not Sebastian can seduce the headmaster’s naive daughter Annette Hargrove.

Through all the backstabbing and bed-hopping, the characters dress impeccably. Costume designer Denise Wingate used wardrobe as a means of defining the characters down to the color palette; Reese Witherspoon’s virginal Annette and Selma Blair’s delightfully dippy freshman Cecile both sport pastel tones and preppy J.Crew cardigans to underscore their innocence. The considerably worldlier Kathryn and Sebastian were dressed in pieces straight off the runways. Their stark, mostly black outfits—is there any shade more appropriate for villainy?—showcased sex appeal and minimalist luxury. Spoiled and unapologetically materialistic—the prize that serves as a catalyst for the entire scheme is a vintage 1956 Jaguar XK140 valued at millions—their aesthetic projected wealth.

Several original pieces were created just for the film, but Wingate mixed them with selections from the era’s biggest labels for added authenticity. The combination made for a moving fashion editorial. No self-respecting 18-year-old girl would wear a wide-brimmed black hat and business suit to lunch in the park, but damn if it doesn’t look good! Several of the best outfits juxtapose Wingate originals with runway styles; the iconic bustier and tulle covered bra combo worn by Gellar was custom but the black suit she wore over it was Dolce & Gabbana. Likewise, Sebastian’s turtlenecks came courtesy of Prada but the rimless glasses were Phillipe’s personal choice.

After 20 years, some elements of the story no longer hold up—a modern reboot would likely feature the girls banding together to block Sebastian’s toxic masculinity instead of falling for his charms—but the clothes are still perfection. Every ’90s trend that currently dominates, from silk slip-dresses to tiny sunglasses, makes its way onscreen and works beautifully together. As the movie heads to the big screen all over again, its teen dream vision is sure to inspire a brand new generation.

See the videos.