The Enduring Influence of 'Cruel Intentions' Fashion: 25 Years of Inspiring Style Legacy

The Enduring Influence of 'Cruel Intentions' Fashion: 25 Years of Inspiring Style Legacy

Exploring how the fashion of the iconic 1999 teen drama seamlessly blends past and present, delivering a narrative beyond elite high schoolers.

The 1999 teen drama "Cruel Intentions" is celebrating its 25th anniversary this week. The story revolves around stepsiblings Kathryn Merteuil and Sebastian Valmont, who engage in a deceitful game against Annette Hargrove and Cecile Caldwell at their prestigious Manhattan prep school.

Based on the 1782 novel "Les Liaisons Dangereuses" by French writer Pierre Choderlos de Laclos, the movie grossed over $70 million at the box office. It also helped propel its stars, including Sarah Michelle Gellar, Ryan Phillippe, Reese Witherspoon, and Selma Blair, further up the ranks of teen A-listers.

“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.

The characters outfits came from a variety of sources including luxury brands such as Prada, Gucci, Calvin Klein and Donna Karan.

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

Filmmakers aimed to set their film apart not just visually from other teen movies of the time, like “Can’t Hardly Wait,” “Jawbreaker,” and “I Know What You Did Last Summer,” but also from the 1988 adaptation of “Dangerous Liaisons” starring Glenn Close, John Malkovich, and Michelle Pfeiffer. They chose to blend 18th-century elegance with 90s sensuality right from the beginning.

In Kathryn’s initial scene, Sarah Michelle Gellar sported a Dolce & Gabbana suit along with a custom corset that Wingate mentions was a direct homage to “Liaisons.” Wingate expressed her admiration for the movie, wanting to pay tribute to it by incorporating period silhouettes into the modern costumes.

JAWBREAKER, center from left: Rose McGowan, Judy Greer, 1999, © TriStar/courtesy Everett Collection

JAWBREAKER, center from left: Rose McGowan, Judy Greer, 1999, © TriStar/courtesy Everett Collection

JAWBREAKER, center from left: Rose McGowan, Judy Greer, 1999, © TriStar/courtesy Everett Collection

TriStar Pictures/Courtesy Everett Collection

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Ryan Phillippe, who played the character Sebastian, received a generous gift of clothes from Prada as he had recently modeled for the luxury Italian brand. Meanwhile, Donna Karan, Gucci, and Calvin Klein were also featured in the characters' wardrobes.

Christine Baranski, who portrayed Bunny Caldwell, Cecile's WASP-y mother, was styled in elegant Chanel-inspired suits from St. John.

The innocence of Cecile is acutely conveyed with this childish koala T-shirt.

The innocence of Cecile is acutely conveyed with this childish koala T-shirt.

The innocence of Cecile is acutely conveyed with this childish koala T-shirt.

AJ Pics/Alamy Stock Photo

Annette and Cecile have a different style compared to Kathryn and Sebastian. They prefer preppy pastels and youthful outfits to highlight their innocence. For instance, Cecile wears a cute koala bear T-shirt in one scene.

But the clash of time periods didn't stop at the outfits. Kathryn's vibrant blue boudoir, carefully crafted on a set in LA, was intentionally different from Sebastian's warmly decorated bedroom. Even his desk was a subtle reference to the 1988 version. Set decorator Tessa Posnansky explained to CNN, "Our production designer, Gary John Steele, had the idea to mix old and new by deconstructing a Louis XIV desk and adding a modern glass top with lights. This custom piece perfectly captured the blend of past and present in the film."


Zoey Grossman/Reformation

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The luxurious Harry F. Sinclair House on Fifth Avenue in New York, named after a former oil tycoon, served as the backdrop for Sebastian and Kathryn's lavish apartment. Posnansky highlighted the striking magenta silk curtains in the living room set, exuding the opulence of the late 90s.

Central Park is unique and cannot be replicated. It was the backdrop for a famous movie scene where Cecile, who has never been kissed before, is taught how to kiss by 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.

A quarter of a century after it's initial release, the clever styling of Cruel Intentions is finding favor with a whole new demographic.

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

Kathryn's outfit, consisting of all-black garments, dark sunglasses, and a Chapeau du Matin-style hat, was a deliberate nod to a famous big screen look. Wingate, the costume designer, drew inspiration from Audrey Hepburn for the park scene in the movie. Sarah Michelle Gellar, who played a role in the film, also loved the idea.

A quarter of a century later, the impact of "Intentions" is still evident, as it has inspired a musical and an upcoming series on Amazon. The styling from the movie can be seen in popular TV shows from the 2000s like "The OC" and "Gossip Girl." Even in more recent times, the finale of Netflix's "Do Revenge," which featured Sarah Michelle Gellar as the school's headmistress, seems to echo the fashion influence of "Intentions."

After drawing inspiration from various sources, the movie "Cruel Intentions" continues to influence a new generation even 25 years after its debut.

Editor's P/S:

The article provides a detailed exploration of the costumes and fashion in the iconic teen drama "Cruel Intentions," celebrating its 25th anniversary. The movie's unique blend of 18th-century elegance and 90s sensuality is evident in the