This article originally appeared on i-D US.

There is always something alluring about the popular, mean-girl group in a high school teen movie, whether it’s Heather Chandler’s crew in Heathers or Regina George’s clique in Mean Girls. These girls are simultaneously admired and hated by their fellow classmates, and to be able to portray that kind of duality in a movie requires a certain je ne sais quoi. Throughout the years we’ve seen some pretty remarkable mean-girl cliques strut through their school halls with panache, but none of them are quite as memorable as Jawbreaker.

Jawbreaker was not a hit at the box office when it was released in theaters in 1999 — exactly twenty years ago today — but it ended up being a cult favorite amongst movie fans, especially those who appreciate the style and charisma of The Bad Girl. It tells the story of a high school girl clique, Courtney, Marcie, Julie, and Liz, known as the “Flawless Four.” The girls kidnap Liz (Charlotte Ayanna) as a birthday prank, stuff a candy jawbreaker into her mouth as a sort of makeshift ball gag, put her in a car trunk to take her to breakfast, and accidentally kill her when the ball gets lodged in her throat.

Jawbreaker’s writer and director Darren Stein says he wanted to explore the idea of a prank that was taken to a dark extreme. “I’ve always loved horror films and was fascinated by these teenage girls in the Valley that kidnapped each other on their birthdays,” Stein explains. Of the decision to make the murder weapon a jawbreaker, Stein says, “I had a fascination with those huge, baseball-size jawbreakers as a kid because they were so bizarre. I was obsessed with the sheer amount of time it would take to lick one down to its core. After a while, licking it would make [people’s] tongues bleed.”

Since the jawbreaker incident happens right at the beginning of the film, we only get to know the deceased, Liz Purr, through her friends and admirers. She’s described as “the teen dream”— pretty, popular, and rich, but nice, too, which makes her wildly different than the typical movie mean girl. In contrast to Liz is Courtney, brilliantly played by Rose McGowan. From Rizzo to Regina George, we’ve seen some pretty vicious teen queens, but none are quite like McGowan’s character. With her jet black hair, curve-hugging pencil skirts, sky-high pumps, and acerbic wit, Courtney earned the nickname “Satan in heels,” the total opposite of Liz’s “Princess Di of Reagan High.” Stein cast McGowan after seeing her play Amy Blue in Gregg Araki’s apocalyptic road trip movie, Doom Generation. “She had a beauty and a bite I hadn’t seen in a modern-day film,” Stein says. “I almost thought it would be too obvious or easy to cast her as Courtney, but it turned out she was exactly what the film needed, and the film wouldn’t exist without her. I feel like the tone of the film is something she understands in her soul, the timelessness, and archness and attitude.”

And while the clever lines uttered by Courtney and company (“Peachy-fucking-keen!”) and the creative, gruesome death-by-candy plot set Jawbreaker apart from other teen movies that came out during the late 90s—of which there were many—it’s the fashion that still sticks out in people’s minds. The girls all wore bright, vintage style clothing: form-fitting cardigans, PVC mini skirts, slip dresses, and corsets in bubblegum colors. The scene of them walking down the school hall in slow-motion in these vibrant, eye-popping outfits is one of the iconic moments in the entire film. “I knew I wanted them to feel timeless and stylized with fashion that felt as hyper-colorful, unexpected, and intimidating as the jawbreaker itself,” Stein says. He knew he wanted a mix of candy and punk: the “innocence of the 50s juxtaposed with femme fatales of the 20s, and punk and fetish looks from the late 70s and early 80s.” Stein turned to Vikki Barrett, who worked with costume designer Mona May on the highly fashionable films Clueless and Romy and Michelle's High School Reunion, to bring his vision to life.

Working with a small budget, Barrett was able to source many of the outfits from LA-based vintage shops like Jet Rag, which is known for its legendary $1 Sunday sale. “We were almost all thrifted. I couldn't afford to do any regular shopping, so it was all thrift store [shopping], and making and building, because sometimes it's cheaper to build clothes when you want a specific look, and the kind of look we wanted wasn't out in stores anyway,” Barrett says. She’d then buy vintage skirts from Jet Rag and tailor them to have more of a retro, pencil silhouette.“I would say, if I was inspired by another movie, it would be Grease. But I didn’t want to use any black,” Barrett says. “I wanted contemporary mixed with the 50s. Stilettos and only vintage purses.”

While the girls’ outfits complemented each other, Barrett also kept the characters’ personalities in mind when curating their looks. “We went more innocent on Julie (Rebecca Gayheart), even though she wore a rubber skirt, and was sexy and all that, but we did that with the colors and fabrics,” Barrett says. “She was just not as severe as Courtney, who was edgier and more into corsets. Julie’s [look] was sweeter and her color palette was much lighter, more pastel, and more romantic.”

Aside from stiletto heels and rubber pencil skirts, another ubiquitous fashion element of Jawbreaker is the monochromatic outfits, especially for Courtney, who wears head-to-toe purple and red. Barrett added small, yet striking details to emphasize this aspect, such as making sure her pantyhose corresponded with her outfit. “I put colored seams in the back of all the pantyhose, so if it were tinted red hosiery, it would have a red seam up the back.”

The other character who constantly wore the same color is Vylette, formerly known as Fern Mayo, the class wallflower-turned-popular girl played by Judy Greer. After Fern ditches her drab clothes for a makeover and reemerges as Vylette, she embraces an all-pink color palette. “The hot pink was meant to symbolize the pinnacle of her ascension to a queen bitch that rivals Courtney,” Stein says. He adds that LA icon Angelyne was a major reference for the character, who dyes her hair platinum blonde, wears hot pink and drives a Corvette. “It would have been perfect for her to have a pink Corvette, but we couldn’t get our hands on one. We should have asked Angelyne!” Stein says.

Marilyn Manson, who was dating McGowan at the time and appeared in a cameo in the film, had a hand in one of the costumes. He had gifted a pastel blue, sleeveless argyle top to McGowan that ended up in one of the scenes. “I think she wore it to set one day and I asked her if we could use it for Courtney in the film,” explains Stein. “She gets to confront Vylette in the girl’s room in that and it wears really effectively against Vyette’s hot pink [outfit] and the stark whiteness of the space.”

The final prom scene also features some pretty unforgettable style choices, such as the silver headband that is wrapped around Courtney’s updo. “That, I have to give Rose credit for,” Barrett says. “I didn't have anything to do with that. I trimmed her dress in silver leather, and I didn't have anything for her hair, because I knew they were going to do this whole crown thing. But for Rebecca Gayheart's character, I sprayed fake flowers to match her dress. Those were in her hair. Then Rose saw that, and thought, "I need something for my hair." Adds Stein, “Rose got the idea for Courtney to have a statement piece in her hair that ends up coming apart when she comes undone. The silver band was pretty ingenious because it unravels in her hair, echoing the black mascara smearing down her face.” So, Barrett walked into the makeup trailer with the leftover leather trim, and the hairstylist created the look.

The sexy colorful costumes and the movie’s irresistible mean-girl clique, made Jawbreaker a classic teen movie that is beloved by many still today. Stein attributes the cult film’s lasting legacy to the fact that it is essentially “the celebration of the bad girl.” Even though Courtney is a villain, he says we still end up rooting for her. “It’s also a female-dominated world where the males are secondary characters or arm candy, where women have the power, and their strength and sexuality are celebrated.” As Courtney would say, “Learn it. Live it. Love it.”