As the film celebrates its 20th anniversary, we take a look at its sartorial legacy
Back in 2014, Darren Stein, the director of 1999 black comedy Jawbreaker, and Rose McGowan, who played the film’s anti-heroine Courtney Shayne – otherwise known as evil incarnated in a pair of satin capri pants or ‘Satan in heels’ as the film so astutely puts it – went head to head. “I think she’s a bit sociopathic, but in the best way,” McGowan said of the character. “She’s a young, budding sociopath.”
Courtney is the ringleader of fictional Reagan High School’s most untouchable quartet, who are commonly known as The Flawless Four. Additional members include Julie Freeman (Rebecca Gayheart), Marcie “Foxy” Fox (Julie Benz), and Elizabeth Purr – a non-speaking role awarded to Charlotte Ayanna, the IRL winner of Miss Teen USA 1993, for context.
Just a few minutes into the opening sequence, Liz comes to a very unfortunate end when a birthday prank involving three members of The Flawless Four and one giant ball of candy, from which the film gets its name, goes hideously awry.
It is here that the already formidable Courtney really starts to flex her manipulative tendencies – making Mean Girls’ Regina George, Cruel Intentions’ Kathryn Meuteuil, and She’s All That’s Taylor Vaughn look positively saintly – as she goes about covering up her friend’s murder by bribing dowdy student Fern Mayo (Judy Greer) with promises of popularity and pink lipgloss beyond her wildest imagination.
For those who haven’t seen the movie, which is now an undisputed cult classic despite being widely panned upon its release almost exactly 20 years ago, where have you been? So as not to reveal any further spoilers – aside from the fact there’s a Marilyn Manson cameo where the singer sports a grotesquely attractive adhesive Ron Jeremy moustache – here, we examine Jawbreaker’s style legacy instead, for which it is perhaps best known.
“Please cover your bosoms this is a learning institution, not a brothel,” Courtney’s teacher Ms. Sherwood says into her student’s cleavage, which has been plumped up by a cherry-red boned corset worn over a white, scallop-edged bra, and paired with a matching pencil skirt and strappy platform sandals in the same hue. Darren Stein had banned black from being worn by any of the characters in the movie, with this particularly bold look setting the technicolour tone that would run throughout, as echoed by other members of the clique.
Fern Mayo, meanwhile, opts for scaldingly hot fuchsia dresses, bustiers, and pants following her transformation into Vylette: Courtney’s new protege. As the film progresses, though, Vylette gains the confidence to step out of her mentor’s shadow, rivalling Courtney’s sexually charged, femme fatale realness with items including a t-shirt emblazoned with ‘BITCH’ across the chest.
In contrast, Julie Benz's Foxy and Rebecca Gayheart’s Julie are slightly more prim in her sartorial choices, as seen for the most part in delicate, spaghetti strap slips teamed with pastel cashmere cardigans with floral and plaid accents, with one particular look – a pale turquoise jacket with princess sleeves – indicative of the latter's slightly sharper moral compass and good nature.
One thing that unites the entire group, though, is the fact that all silhouettes remain skin-tight and hyper-feminine throughout the film, with fabrics that are clingy, plasticky, and highly synthetic all featuring heavily. The look is an unadulterated, 1990s take on 50s kitsch at its very best. Or, as Courtney Shayne herself would say, “peachy fucking keen.”
The clothes in Jawbreaker are particularly impactful as they serve as a day-glo contrast to the darkly comedic tones of the film’s plot. Additionally, they highlight the idiom ‘never judge a book by its cover’, as what lies beneath Courtney Shayne’s immaculate exterior is a chapter and verse example of how to (almost) get away with murder.
Darren Stein chose Vikki Barrett, who worked with wardrobe designer Mona May on Clueless (1995) and Romy and Michelle’s High School Reunion (1997), to assemble the costumes for Jawbreaker. Sure enough, Barrett knew a thing or two about where to source the kind of campy, fluorescent clothes that would put Pedro Almodovar’s Women on The Verge of a Nervous Breakdown into a state of hysteria. This was, in fact, mostly at Los Angeles vintage stores, with some pieces even purchased for the bargainous price of $1 each.
The fashion in Jawbreaker speaks of a particular moment in history just before the rapid ascent of social media, when Instagram was but a glint in the eye of its founder, and adolescents treated the halls of their high school – rather than their phone screens – as a place for sartorial peacocking.
Nevertheless, Generation Z has taken style notes from the film time and time again, scouring Depop and online stores such as Pretty Little Thing and Fashion Nova to source 1990s-inspired garms more than worthy of The Flawless Four. Even the likes of Kendall Jenner, Hailey Bieber, Kylie Jenner and Bella Hadid – a modern-day iteration of the teen pin-up girl – have been spotted out and about, in neon, Jawbreaker-esque looks.
The runway, too, has seen many collections riffing on the film’s costumes: Donatella Versace’s AW19 collection for the Italian house, staged just last week in Milan, embraced the codes of her late brother Gianni’s design, which in turn perhaps influenced the fashion in the ‘90s teen film genre like no other. Our bets are on it only being a matter of time until a designer cites the film as a direct reference: Jeremy Scott, over to you.