Reese, Sarah Michelle, Selma & Ryan: The ‘Cruel Intentions’ Premiere Looks That Defined ’90s Fashion

If you were around in 1999, Cruel Intentions almost certainly crossed your path. What began as a modest indie project quickly snowballed into a teen-drama sensation, captivating late-’90s audiences with its mix of privilege, seduction, and razor-sharp dialogue.

Adapted from the 1782 French novel Les Liaisons dangereuses, writer-director Roger Kumble reimagined the classic tale for Manhattan’s elite prep-school set—delivering a richly stylized, high-gloss version of teenage manipulation that instantly resonated with moviegoers.

But beyond the scandalous plot, it was the film’s rising-star cast—Reese Witherspoon, Ryan Phillippe, Sarah Michelle Gellar, and Selma Blair—that turned Cruel Intentions into a cultural touchstone. Their breakout performances, paired with a string of glamorous red-carpet appearances, helped cement the movie’s place in late-’90s pop-culture history.

And at the Westwood premiere, the young cast leaned fully into the era’s fashion—crinkled skirts, minimalist sandals, oversized suiting, and all.

Helmed by rising talents like Reese Witherspoon, Sarah Michelle Gellar, Ryan Phillippe, and Selma Blair, Cruel Intentions earned mixed reviews upon release. However, they quickly gathered the kind of cult devotion that still defines it today.

Selma Blair’s Breakout Moment: Cecile Caldwell, ’90s Minimalism, and Red-Carpet Style

And while the glossy mix of drama, sex, and seduction certainly helped, the young cast’s magnetic performances—especially Selma Blair’s turn as Cecile Caldwell—played a major role.

Blair was 26 when the film debuted on March 5, 1999, celebrating her 27th birthday a few months later on June 23, 1999.

Selma Blair channels quintessential late-’90s minimalism in a black cropped tank, a flowing white satin maxi skirt, and barely-there strappy black sandals that peek out from beneath the hem at the’Cruel Intentions’ Westwood Premiere on February 25, 1999, at Mann Village Theatre in Westwood, California (Credit: Featureflash Photo Agency / Shutterstock)

Sarah Michelle Gellar’s Breakout Era: From Buffy Stardom to ’90s Red-Carpet Glamour

As a child actress in the 1980s, Sarah Michelle Gellar landed a handful of minor roles before breaking out on the soap opera All My Children in 1993. She left the series two years later—and it proved to be a smart move.

In 1997, Gellar landed the title role in Buffy the Vampire Slayer, the cult TV phenomenon that made her a household name. She followed it with back-to-back big-screen hits, including I Know What You Did Last Summer and Scream 2, the same year.

Sarah Michelle Gellar lights up the Cruel Intentions premiere in a slinky black dress with sequined sheer paneling, finishing the look with glossy square-toe slingback heels that epitomize late-’90s red-carpet glamour (Credit: Featureflash Photo Agency / Shutterstock)

By the time Cruel Intentions premiered in 1999, Gellar was just 21, celebrating her 22nd birthday shortly after on April 14.

Sarah Michelle Gellar embodies Kathryn Merteuil’s seductive power in a corseted slip dress with delicate satin straps—an iconic late-’90s look that captures the character’s polished, dangerous allure in Cruel Intentions (1999) (Credit: Sony Pictures Releasing)

Reese Witherspoon’s Early Rise: From Child Prodigy to ’90s Breakout Star

Hailing from New Orleans and born in 1976, Reese Witherspoon made her acting debut after auditioning for a small part in the 1991 film The Man in the Moon.

Much to her surprise, the then–15-year-old landed the lead role of Dani Trant, instantly marking her as a young talent to watch.

Reese Witherspoon steps onto the Cruel Intentions red carpet in a color-blocked crinkled skirt and minimalist strappy sandals, while Ryan Phillippe keeps it relaxed in a loose-cut black suit and polished dress shoes at the ‘Cruel Intentions’ Westwood Premiere on February 25, 1999, at Mann Village Theatre in Westwood, California (Credit: Featureflash Photo Agency / Shutterstock)

She followed that breakout performance with starring roles in A Far Off Place (1993) and S.F.W. (1994), further cementing her early promise. But it was Freeway (1996)—a dark, offbeat comedy in which she played the relentless Vanessa Lutz—that brought her the most attention during this phase of her career.

Reese Witherspoon keeps it simple and chic in a white dress with a vibrant orange ribbon at the Cruel Intentions Westwood premiere on February 25, 1999 (Credit: Featureflash Photo Agency / Shutterstock)

Although the film earned strong critical praise—particularly for Witherspoon’s performance—it struggled at the box office, and she was just 20 when it was released.

1998 proved to be a packed year for the actress, who landed roles in Overnight Delivery, Pleasantville, and Twilight. Despite favorable reviews for her work in Pleasantville, none of the projects became major commercial hits.

By 1999, Witherspoon was already a seasoned young star, even if she had yet to headline a true box-office breakout.

Reese Witherspoon keeps it sleek in a fitted black midi dress, soft cardigan, and minimalist strappy sandals, arriving hand-in-hand with Ryan Phillippe at the Cruel Intentions Westwood premiere on February 25, 1999 (Credit: Startraksphoto)

While Cruel Intentions was in pre-production, Witherspoon was already dating her co-star Ryan Phillippe, whom she had first met at her 21st birthday party in 1997.

Reese Witherspoon and Ryan Phillippe share a tender moment in a scene from Cruel Intentions, where they played the characters Annette Hargrove and Sebastian Valmont (Credit: Sony Pictures Releasing)

The two married shortly after the film’s release—a whirlwind romance she later joked about, recalling how she told him, “I think you’re my birthday present,” after one too many Midori sours.

Ryan Phillippe was 24 years old when she attended the premiere of Cruel Intentions in 1999 (Credit: Featureflash Photo Agency / Shutterstock)

Ryan Phillippe’s Rising-Star Moment: Charisma, Complexity, and Late-’90s Style

The film performed modestly at the box office but received lukewarm reviews. Still, by 1999 Ryan Phillippe was a rising star, and his casting as Sebastian Valmont felt inevitable given his talent for playing charismatic, morally conflicted characters.

At 24, he was the oldest of the film’s three leads, celebrating his 25th birthday later that year on September 10. His character remains one of the movie’s most intriguing—introduced as a calculating womanizer but ultimately undone by genuine emotion for Annette, played by Reese Witherspoon.

And just like the story itself, the film’s wardrobe tells its own tale: a razor-sharp blend of late-’90s prep-school polish and dark, seductive sophistication inspired by its 18th-century source material, Dangerous Liaisons.

The core cast of the 1999 teen drama poses in peak ’90s luxe minimalism—sleek slip dresses, strappy block-heel sandals, and dark tailored eveningwear—capturing the film’s signature mix of prep-school polish and seductive edge (Credit: Sony Pictures Releasing)

Explore More Style Moments From the Cruel Intentions Cast

Before we wrap, it’s worth noting that the film’s influence didn’t end in 1999—its stars went on to deliver some of the most memorable shoe and fashion moments of the late ’90s and early 2000s. For readers who want to dive deeper into their style evolution, here are a few standout highlights from across Your Next Shoes.