Fashion is, by nature, a nostalgic endeavor: it looks ahead by reaching back in time. The industry draws upon styles from seasons past that can be reinvented, and as recent years attest, the 1990s in particular offered a wealth of looks that are currently enjoying an infusion of new life. Nowhere did the decade’s aesthetic latitude better capture the attention of consumers than through movies: teen dramas and romantic comedies abounded, bequeathing us an infallible time capsule of outfits and fashion trends that are yet again in vogue and worthy of further inspiration reconnaissance.
Here, we’ve assimilated the stand-out pieces and styles sourced from some of the most iconic ’90s movies alongside their 2021 reincarnations.
While You Were Sleeping (1995)
Brief synopsis: In this classic “huge misunderstanding” rom-com, protagonist Lucy Eleanor Moderatz (played by Sandra Bullock) is a lonely Chicago transit worker who saves a stranger with excellent eyebrows from being hit by a train, only to accidentally convince his family that she is his fiancée. While well-browed stranger (Peter Gallagher) is in a coma, Lucy falls in love with his brother (Bill Pullman), confronts her own sense of isolation, and dresses extremely comfortably.
Fashion inspo: The chunky knit sweater. It’s hardly surprising that a film premised upon a central character remaining in bed would serve up an array of ever-more hygge ensembles in oversized proportions. Lucy has much to teach even the most devoted of 2020’s loungewear recruits about boxy knits, wool beanies, and cozy layering: for example, ideally your sweater should be large enough to lose a modest Christmas gift within its sleeves. Ultimately, ubiquitous cable knit renders a far-fetched scenario – and a broader commentary on loneliness and belonging – touchingly relatable, and the film’s cast of warm top layers serves as a reminder that a simple sweater is perennial.
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Clueless (1995)
Brief synopsis: An updated, soft-satire version of Jane Austen’s Emma finds its setting in Beverly Hills, where high school queen bee Cher Horowitz (Alicia Silverstone) takes it upon herself to mentor awkward transfer student Tai Frasier (Brittany Murphy). Through witty one-liners and Cher’s self-involved but occasionally poignant and philosophical narration, the film humorously critiques gender and class to a backdrop of girls fighting over Paul Rudd.
Fashion inspo: Plaid and checks. It’s hard to find anyone capable of wearing brightly colored plaids as confidently as a Valley girl blue blood, but Cher’s inherent likability makes her ensembles that much more winsome. Throughout the movie, she and the crew (including BFF Dionne, who knows how to rock a preppy ensemble) embrace bold graphic motifs, sporting everything from pinstrip power blazers to argyle mini-skirts.
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Romeo + Juliet (1996)
Brief synopsis: Baz Luhrmann’s gaudy Verona Beach adaptation of the Shakespearean tragedy layers bombastic contemporary visuals atop the original plot and 16th century language. Star-crossed teenagers Romeo Montague (baby-faced Leonardo DiCaprio) and Juliet Capulet (Clare Danes) impetuously fall in love to a soundtrack of Radiohead and Des’ree but…you know the rest. This ending never becomes a happy one.
Fashion inspo: The romantic white dress for every occasion. Although this sumptuously reimagined world for the Bard’s Elizabethan English was very much geared towards the MTV generation, Clare Danes’ array of snow-white gowns remains timeless, elegant, and a calm counter-point to the feud and chaos surrounding her. Her most iconic look from the film – the waist-defining angel costume she dons the evening she meets Romeo, complete with a set of wings – is simple yet flattering. The all-white-everything dress is more than just a trend; it’s a reliable fashion recurrence season upon season, and almost 25 years after Romeo + Juliet, it still holds uncompromised style cachet.
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Never Been Kissed (1999)
Brief synopsis: Insecure copy editor Josie Gellar (Drew Barrymore) is tasked with posing as a high school student to conduct research for an investigative feature. The problem: Josie’s own high school experience was a nightmare hellscape. With help from her brother (David Arquette), Josie infiltrates the “cool clique,” where James Franco and Jessica Alba make their cinematic debuts. But the plan hits a major snag when she falls for her English teacher (Michael Vartan). Ultimately, this classic of the teen movie genre is the story of a woman’s journey to self-acceptance and a catalog of Halloween-ready prom outfits.
Fashion inspo: Cardigans. When Josie’s newfound gal-pals take her to the mall for an image makeover, the entire group is soon spotted in a rainbow of soft cardigans that are just as wearable today as they obviously were in 1999. From the classroom to the baseball stadium, cardigans are the unsung heroes of the movie, seen layered over tanks and shirts but also worn buttoned-up as stand-alone tops à la Bella Hadid & Kendall Jenner. (Fun fact: both were toddlers when Never Been Kissed hit theaters).
Psst – you can read our guide to wearing and styling the current cardigan trend in 2021 here.
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She’s All That (1999)
Brief synopsis: High school hot shot Zack Siler (Freddie Prinze Jr.) finds his popular status threatened when his girlfriend breaks up with him. Desperate to re-establish his reputation, he agrees to a daunting challenge: gain the trust of dorky outcast Laney Boggs (Rachael Leigh Cook), and turn her into the next prom queen. As if any amount of nerdiness could disguise RLC’s exquisite bone structure.
Fashion inspo: The drawstring neckline. In the movie’s pinnacle makeover reveal scene, Laney stuns Zack when she appears in a crimson spaghetti-strap slip dress to accompany him to a party. The effect is strong enough to cause an atrociously carpeted flight of stairs to fade into the background (and that’s saying something). With its flattering peasant-like neckline – now very much epitomized by it-girl labels like Réalization Par – the dress made a lasting impression on audiences. Just type “Laney Boggs” into a Google search and the first key phrase to emerge proves that plenty of viewers are still on the hunt for a similar look.
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