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

“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.

The characters outfits came from a variety of sources including luxury brands such as Prada, Gucci, Calvin Klein and Donna Karan. - Bob Frame/Columbia/Kobal/Shutterstock
The characters outfits came from a variety of sources including luxury brands such as Prada, Gucci, Calvin Klein and Donna Karan. - Bob Frame/Columbia/Kobal/Shutterstock

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.

The innocence of Cecile is acutely conveyed with this childish koala T-shirt. - AJ Pics/Alamy Stock Photo
The innocence of Cecile is acutely conveyed with this childish koala T-shirt. - AJ Pics/Alamy Stock Photo

In direct contrast to Kathryn and Sebastian’s mature and dark colored looks, both Annette and Cecile appear in preppy pastels and more youthful styles to showcase their naivete (in one scene, Cecile wears an “adorable” koala bear T-shirt, for example).

But the period-clashing juxtapositions didn’t end with the clothes. Kathryn’s deep blue boudoir — created on a sound stage in LA — was a deliberate contrast to Sebastian’s autumnally toned bedroom, in which his desk was also a subtle nod to the 1988 adaptation. Set decorator Tessa Posnansky told CNN, “(production designer, Gary John Steele) came up with the idea to deconstruct a Louis XIV desk and add a lighted glass top, pairing old and new so we had that custom-built for us.”

The opulent Harry F. Sinclair House on New York’s Fifth Avenue — named after the oil tycoon who once lived in the residence — was the location of Sebastian and Kathryn’s decadent apartment. “My favorite element of the living room set was the bold magenta silk curtains that spilled to the floor in all the decadence that the late 90s would allow,” Posnansky said.

Central Park has no replica and indeed it formed the set for one of the movie’s most iconic scenes in which Cecile, who has never been kissed, learns how to do so from Kathryn.

A quarter of a century after it's initial release, the clever styling of Cruel Intentions is finding favor with a whole new demographic. - Melissa Moseley/Columbia/Kobal/Shutterstock
A quarter of a century after it's initial release, the clever styling of Cruel Intentions is finding favor with a whole new demographic. - Melissa Moseley/Columbia/Kobal/Shutterstock

Wrapped in all-black garments with dark sunglasses and Chapeau du Matin-style hat, Kathryn’s look was a deliberate reference to one of the big screen’s most famous outfits. “I was definitely inspired by Audrey Hepburn for the scene in the park,” Wingate says. Sarah (Michelle Gellar) and I both loved the idea.”

A quarter of a century on, the influence “Intentions,” had — and continues to have — is undeniable, spawning a musical and a forthcoming series from Amazon. Its styling references can be seen in noughties hit shows “The OC,” and “Gossip Girl,” and, more recently, the finale of Netflix’s “Do Revenge,” (which co-starred Sarah Michelle Gellar as the school’s headmistress), seemingly echoes that of “Intentions.”

Despite being an adaptation that took its cues from a plethora of existing works, 25-years after its initial release, “Cruel Intentions” is, it seems, providing the very same inspirations for a whole new generation.

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