‘Cruel Intentions’ Proves That Being Rich, Hot, and Toxic Never Goes Out of Style

The cult classic teen film is celebrating 25 years of being bad and looking good.

The prevailing fashion trends of 1999 seem eerily familiar today. The athleisure, relaxed silhouettes, chokers, and Canadian tuxedos that were all over MTV’s Total Request Live and shows like Dawson’s Creek and Buffy the Vampire Slayer dominate social media in 2024.

But even before TikTok (and Tumblr before that) reigned as the platform of choice for fashion girls and gays who needed a repository for vibes and veneration, one particular cinematic masterpiece stood above the rest: Cruel Intentions, the R-rated movie that saw Sarah Michelle Gellar playing against type and Ryan Phillippe post-I Know What You Did Last Summer, acted as a much-needed bitter palate cleanser from the saccharine sweetness of the teen movies (Drive Me Crazy, Varsity Blues, and 10 Things I Hate About You) that hit theaters in 1999.

At the time, the film had moms clutching their pearls — a style that also happens to be back in a big way, mind you —  and critics dismissing it entirely because of the titillating plot, the sexualized promotional posters, and one headline-making cameo from Phillippe’s butt. 25 years later, that scandal has dissipated, but one thing remains the same: The characters’ slick style is still inspiring the internet. Only this time, it’s Gen Z who has adopted the Cruel Intentions aesthetic and remixed it into soft goth, stealth luxury, and Succession-core.

Cruel Intentions is based on the 1782 French novel Les Liaisons Dangereuses (Dangerous Liaisons) by Pierre Choderlos de Laclos. Gellar, who wanted to play against type with a character as far away from Buffy Summers as possible, stars as Kathryn Merteuil, the self-professed “Marcia fucking Brady of the Upper East Side” alongside Phillippe’s Sebastian Valmont, her stepbrother. The film famously includes Gellar kissing her co-star Selma Blair and Phillippe trying to seduce Reese Witherspoon’s character, Annette Hargrove. The two were dating off-screen at the time, which added another layer to the public’s fascination with the movie — not to mention Gellar’s famous line, “you can put it anywhere,” which earned the film an R rating in 1999. Today, it’s standard fare for Love Island.

To cut through the camp and conniving, Emmy Award-winning costume designer Denise Wingate, whose work can be seen on Prime Video’s Daisy Jones and the Six, She’s All That (a decidedly more wholesome film involving a bet that also celebrated its 25th anniversary this year), and A Cinderella Story, set out to dress the cast in a way that was distinct and very grown-up.

“The initial idea was that these wealthy kids were dressing like adults,” Wingate tells InStyle. “I tried really hard to design the costumes in such a way that they would be fashionable, classic, and timeless.”

On-screen, that meant elegant tailoring and avoiding logos and anything flashy. In one of the film’s opening scenes, Gellar unbuttons her suit jacket to reveal a corset underneath — which is an outfit that would look right at home on the red carpet in 2024. Wingate notes that while she’s not on TikTok (and acknowledges that she knows her work on Daisy Jones also went viral on the platform), she’s happy that some of the looks in Cruel Intentions feel fresh enough to be relevant in the internet age.

“I love when people respond to my costumes,” she says. “If the work I have done contributes to fashion trends, it is a huge compliment.”

But back to that corset. Not only was the look just the right amount of scandalous, but it established Kathryn’s character and set the fashion tone for the rest of the film. Cruel Intentions is all about projecting a certain propriety to distract from the salacious betrayal and schemes that lie underneath. That façade seduced teen audiences back at the turn of the millennium, making the film a hit in theaters, where it debuted at no. 2 behind Analyze This, and continues to captivate today.

“The first outfit we meet Kathryn in — she is wearing a black Dolce & Gabbana suit, which looks pretty upscale and conservative — until she removes the jacket and she’s wearing a corset,” Wingate notes. “Nothing is as it seems in this film.”

There are other flashes of Old Money dressing in the first few minutes of Cruel Intentions. There’s what looks like a Cartier watch and an Elsa Peretti Tiffany & Co. Bone cuff on Swoosie Kurtz’s character, Dr. Greenbaum. Wingate laughs at the thought that the production could afford those items for the shoot. While it may be heartbreaking for fans to learn, those big-ticket items were probably not the real deal.

“I guarantee that it was not a Tiffany cuff. Our budget was very minimal, so I’m sure it was just something resembling that style,” she says. According to Vice, the film was made for $11 million — to put that number into context, this year’s Mean Girls remake cost $36 million. “Props did the watches, and it’s possible that she had a Cartier watch that was rented or loaned. Because we didn’t have a big budget, it made it even more difficult to dress everyone to look so stylish and wealthy.”

That fun fact should satisfy much of TikTok, especially users who get a rush when they find a dupe for covetable pieces, especially jewelry. One piece of jewelry, in particular, is so closely associated with Cruel Intentions that it’s become the unofficial symbol of the film — and maybe even teenage rebellion at large. Kathryn’s rosary unscrews to reveal a tiny spoon and her stash. Wingate says that the prop was made specifically for the film. Lynda Reiss, the on-set genius behind the rosary (her stacked résumé includes corralling the rose petals in American Beauty, finding the bikes for Stranger Things, and making sure the beer cans in True Detective are just right), went through multiple designs before settling on the jewel-encrusted piece that’s in the movie.

“It was in the script, and I know there were a lot of discussions and drawings of it before it was made,” Wingate says of the iconic rosary. “I have no idea where it is now, but I love the hypocrisy of the symbolism.”

Other shows have followed Cruel Intentions’s lead in more ways than viewers might realize. Wingate’s fake-it-’till-you-make-it mindset may have inspired the crew at The OC, which allegedly used knockoff bags for filming. And Gossip Girl’s signature Upper East Side gloss? There’d be no Constance Billard or St. Jude’s without Manchester Prep: both fictional schools had strict dress codes that happened to be ignored when their queen bees got dressed. Wingate also admits to scouring Goodwills and Salvation Army locations for the background actors’ uniforms — another detail that’ll appeal to TikTokers and their love of vintage.

“I watched the movie again not too long ago, and I was surprised at how well some of the costumes held up,” Wingate adds. “They are a bit iconic at this point.”

Fans sometimes forget that Cruel Intentions was an update to 1988’s Dangerous Liaisons, with Michelle Pfeiffer, Glenn Close, and John Malkovich. That was a full-on period piece, but Wingate says she paid homage to the flick in very subtle ways — fans may need to re-watch their favorite scheming step-siblings to catch a glimpse.

“I really loved the 1980s film version of Dangerous Liaisons and wanted to mix some period garments with contemporary clothes,” she says. “The long black coat Sebastian is wearing at the end of the film, I had made. It was based on a turn-of-the-century frock coat. I lined it with a bright maroon silk lining. It was a great piece.”

Reflecting on the 25 years since the movie’s release, Wingate remembers Cruel Intentions as one of her favorite projects — it was, in fact, just her second feature-length project after cutting her teeth on Melrose Place. Clothes aside, she thinks that it would be impossible to recreate that magic today.

“There would be no way anyone would make this film now. We are living in an entirely different time,” she says. “I’m just happy I was able to be a part of something that was so bold and creatively rewarding. It was also the most fun I have ever had on a film.”

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