Why the style legacy of ‘Cruel Intentions’ still inspires, 25 years on

The styling of the 1999 teen drama manages to deftly marry the old and new to tell a story about far more than just privileged prep schoolers.

“Cruel Intentions,” the 1999 teen drama which celebrates its 25th anniversary this week, tells the story of spiteful stepsiblings Kathryn Merteuil (Sarah Michelle Gellar) and Sebastian Valmont (Ryan Phillippe) as they wage a twisted game of deception against Annette Hargrove (Reese Witherspoon) and Cecile Caldwell (Selma Blair) at their elite Manhattan prep school. Grossing over $70m at the box office — and pushing its stars even further up the teen A-lister charts — the movie is an adaptation of French novelist Pierre Choderlos de Laclos’ 1782 novel “Les Liaisons Dangereuses.” “We had a very small budget (the entire movie was reportedly made for $10.5m), so we had to be really creative with the looks,” costume designer Denise Wingate told CNN. Keen to establish itself not only as a visual departure from teen films released around the same time — think “Can’t Hardly Wait,” “Jawbreaker” and “I Know What You Did Last Summer,” — but also from the 1988 film adaption of “Dangerous Liaisons,” starring Glenn Close, John Malkovich and Michelle Pfeiffer, filmmakers decided from the outset to marry 18th-century elegance with 90s sensuality. In Kathryn’s first scene, Sarah Michelle Gellar wears a Dolce & Gabbana suit paired with a custom corset Wingate says was a direct nod to “Liaisons.” “I loved that movie and wanted to acknowledge and honor it by putting some period silhouettes in with the contemporary costumes,” she explained. While Donna Karan, Gucci and Calvin Klein featured in the characters wardrobes, Ryan Phillippe was sent “a big box of clothes” from Prada for his Sebastian character, as the actor had recently modelled for the luxury Italian house, Wingate said. Christine Baranski, who appears as Bunny Caldwell – Cecile’s WASP-y mother – was adorned in Chanel-style suits from St John.