Jawbreaker's Iconic Fashion Moments Pioneered Today’s Biggest Trends

Clueless. Romy and Michele’s High School Reunion. The Devil Wears Prada. These are just a few titles that likely come to mind when you think of iconic fashion flicks that stand the test of time. Another one that may not immediately jump at you is 1999 cult classic Jawbreaker. Starring Y2K starlets Rose McGowan, Rebecca Gayheart, Judy Greer, and Julie Benz, the dark teen comedy has been a definite slow burn, showing its sustaining fashion influence in more subtle ways. However, pop culture and fashion anthropologists can’t deny the campy film’s pioneering efforts that are relevant to this day.

Inspired by the equally memorable Heathers, Jawbreaker tells the tale of a prank gone wrong, when an exclusive clique of high school queens — dubbed the “Flawless Four” — accidentally murder one of their own with, that’s right, a Jawbreaker. The film’s cutting one-liners live in infamy (“I killed Liz, I killed the teen dream — deal with it”), but it’s the retro-inspired, candy-coated fashions that have been forever immortalized in the pop culture zeitgeist. In fact, Jawbreaker’s impact was clear as day at the recent 25th Anniversary party in West Hollywood, hosted by social media marketing tool Planoly and F.L.U.I.D, a newly launched independent production studio and film fund dedicated to LGBTQIA+ stories. (Planoly and the Jawbreaker cast have been hosting a search for a fan-designed Jawbreaker emoji to time with World Emoji day on 7/17). Attended by director Darren Stein as well as Gayheart, Greer, and Benz, the late night extravaganza drew a crowd that included die-hard millennials who were raised on the film’s monochromatic cardigan-clad ensembles as well as newly converted Gen-Zers.

“I think what Vikki [Barrett] and Darren created was a kind of modern take on a classic look and classic lines,” says Benz to TZR, referencing the film’s costumer designer and director’s stylish vision. “That's why, it wasn't trendy. It was just taking the 1950s style and making it a little more modern. And that's why we still see it resonating today.”

Costume designer Vikki Barrett was inspired by classic retro fashion motifs, and set these standards against vibrant rainbow palettes, specifically shades found in the namesake candy. “We wanted it to be sweet and sugary-looking,” Barrett told CNN in a recent interview. “And then it takes a turn. We tried not to use any dark or moody colors at all, and keep it really light, festive and fun, so that the element of darkness would be a surprise.” The designer explains each character had their signature shade — for example, Marcie “Foxy” Fox (Benz)was often in lime green, queen bee Courtney Shane (McGowan) was in regal colors of rich red, and geek-turned-swan Fern Mayo aka “Vylette” (Greer) was in bright pinks.

“That's the most fun role always to play is the role that changes the most, whether it's physically or emotionally, to have the biggest journey to go through,” says Greer of her iconic Marilyn Monroe-like transformation in the film. “I really loved the makeover.”

Each look in the film demonstrated Barrett’s penchant for a monochromatic moment — pairing fitted cardigans with coordinating cigarette pants and hip-hugging pencil skirts — which was also ahead of its time. These days the look is a go-to for Hollywood’s It girls as well as social media’s fashion elite.

Benz, who played Foxy in the film, said the role had an unexpected impact on her personal style. “So before Jawbreaker, I never really wore high heels,” she says to TZR at Jawbreaker’s July 12th anniversary party (wearing a mini dress in Foxy’s signature green). “And I realized, while filming the movie, that I didn't know how to walk in high heels. And then I saw the movie, and it confirmed that. So, then I had to learn how to walk in high heels.”

Greer said she kept a lot of her “Vylette” items as she loved all the shiny pink “b*tch” outfits. I really loved the lamé tube top and pencil skirt I wore,” she says. Gayheart, who played Julie Freeman, says her mod accessories were a favorite for her. “I loved my hoops, I loved my glasses,” she says. “The retro glasses were so good! I also loved the latex skirt I wore when we were carrying the dead body, that was cool.”

Channel your own “Flawless Four” character with the Jawbreaker-inspired outfits and accessories below.