Editor’s Note: Delving into the archives of pop culture history, “Remember When?” is a CNN Style series offering a nostalgic look at the celebrity outfits that defined their eras.
Remember when high schoolers ruled the world? In the ’90s, so many of our favorite films starred plucky teens: a headstrong Julia Stiles in “10 Things I Hate About You,” a devious Sarah Michelle Gellar in “Cruel Intentions,” a cunning Reese Witherspoon in “Election.” But one of those teens has proven more lasting than the rest: Alicia Silverstone’s Cher, from “Clueless.”
The character has been a mainstay in popular culture ever since she first appeared in 1995. Based on Jane Austen’s “Emma,” Cher Horowitz is a popular rich girl who’s always meddling in everyone else’s business. Under the guise of charity, she intervenes in the life of Tai, her school’s “tragically unhip” new kid, making her over and serving as her guide to popularity – until Tai admits her feelings for Cher’s ex-stepbrother, who Cher likes too. We could spoil the ending, but you probably already know it.
Cher continues to have a grip on popular imagination for a few reasons: There’s Silverstone’s winning performance, which somehow renders the character both bratty and loveable. There’s the script, littered with one-liners and catchphrases we still parrot today (“As if!”). But most of all, there are her clothes. If you somehow missed the parade of Chers this Halloween (and every Halloween since 1995), the most iconic Cher outfit is this: a preppy blazer-and-pleated-skirt combo in bold lemon.
In an opening scene, she wears it to her school with her best friend Dionne, who also wears a plaid blazer and skirt, though hers is a more understated black pattern with red accents. Next to it, Cher’s outfit is so bright, you can’t take your eyes off her.
“We wanted to make sure that she popped because she’s going to be in the quad with a lot of green around her, a lot of other kids,” costume designer Mona May told Entertainment Weekly in 2015. “It was so important to choose the first look.” Elaborating further, May said: “It’s like taking the uniform and twisting it. What would Cher do with a Catholic school girl uniform? Take it to another level: Let’s make it a Dolce & Gabbana yellow suit with over-the-knee stockings and matching Mary Janes and the furry backpack and, of course, beautiful hair.”
The fashion doesn’t end after the first scene. The whole film is a visual feast for ’90s fashion buffs: A white Calvin Klein mini dress for date night, an ‘80s-style blazer and argyle skirt for a day out shopping, a red Alaia party dress, a pinstriped blazer and beret for school. All of these are imbued with Cher’s signature ensembles – a twist on classic fashion pieces that makes otherwise stuffy clothes look fun.
As the film gets closer to its 25th anniversary in 2020, a wave of “Clueless” nostalgia has emerged.
Last fall, fast-fashion brands including Urban Outfitters and Forever 21 sold yellow plaid blazers in a not-so-subtle nod to the film. Earlier this year, sneaker brand K-Swiss released a line of “Clueless”-inspired shoes that read “As if!” on the soles. Alicia Silverstone herself wore the outfit again for her turn on Lip Sync Battle, mouthing the words to “Fancy,” a song released in 2014 whose video also features a “Clueless” homage.
It makes sense that Cher has such a hold on us today: we’re in the midst of a ’90s revival.
Celebrities are wearing tiny sunglasses and spaghetti straps again and reboots of old shows, like “Sabrina the Teenage Witch,” are taking over Netflix. Earlier this year, a song called “1999” charted on the Billboard Top 40, with Charli XCX singing over the chorus: “I just wanna go back, back to 1999.”
Amid all the collective wistfulness, another reboot was announced. Deadline reported in October that a “Clueless”-inspired TV series had grabbed network attention. Only this time, Dionne will star.