a film-girl's guide to preppy

Cher Horowitz has never done anything wrong.

In the 1980s, American fashion brands Tommy Hilfiger and Calvin Klein brought the sweaters, knitwear, denim, collared button-ups and blouses, leather shoes, and pearl jewelry common on the quads of Ivy League campuses into the realm of commercial fashion. Their takes on the preppy style housed behind the gilded gates of upper-class institutions since the turn of the 20^th century spurred on the popularity of purist adoptions of preppy style and contemporary adaptations of preppy pieces and the preppy ideal, amongst young people during the decade.

Michael Lehmann’s Heathers (1986) satirically revels in the pristine poshness and rigid rules of the film’s titular elite high school clique and the shiny croquet-playing suburbs that the clique’s founding members Heather Chandler, Heather McNamara and Heather Duke belong to. To match the film’s satirical tone, the Heathers’ clothing is uber-preppy – oversized plaid blazers with shoulder-pads, jewel-toned fitted blazers and matching knee-length skirts, starched blouses, finely-textured Sweetheart-neckline cocktail dresses, Dior little black dresses, double-breasted belted coats, thick pleated plaid skirts, opaque tights and knee-length socks, Mary Jane shoes, and golden brooches. Winona Ryders’ bookish outsider Veronica Sawyer shares in this look, wearing an oversized, patchwork, double-breasted sweater, narrow blazers, powdery button-ups, knit vests, thick pleated skirts, tiered plush skirts, a fitted, suede cocktail dress, and Bowler hats, all in compatible shades of royal blue, black and grey.

As in Heathers, fashion is a main character in Amy Heckerling’s Clueless (1995), though in the latter film it is a form of autonomy and a means of artistic expression and creativity for the pair of Beverly Hills’ teen-girl best friends at its centre, Cher Horowitz and Dionne Davenport. Cher and Dionne’s fashion embody the classy and polished ethos of preppy dressing, though their garment choices pulls this ethos into the glamorous, glossy magazine 1990s. Alicia Silverstone’s Cher’s style is ultrafeminine and sweet, with her character wearing soft, pastel collared shirts, knit camisoles, skirts and cardigans, plaid and checkerboard skirts, a variety of satin and corduroy mini-dresses, oversized peacoats, knee-high socks, strappy heels, and her iconic three-piece honey-yellow set. Stacey Dash’s Dionne’s style is more high-fashion and cultured, with her character going for bold, edgy plaids (including her iconic three-piece black-and-red set), collared, velvet mini-dresses in royal tones, textured and decorated knitwear, leather and latex mini-skirts, layered lacey and sporty pieces, layered jewelry and statement hats, and like Cher, favouring monochromatic palettes. Even Tai, Brittany Murphy’s sporty transfer student, has her own cool, casual play on preppy by the end of the film, comprising of preppy-patterned short-sleeved tops, cropped flannels, loose cardigans, long-sleeved tops in sweet colours, boyfriend jeans, overalls, and simple necklaces.

The Fresh Prince of Bel-Air’s Ashley Banks (Tatyana Ali) has a more playful, down-to-earth take on preppy fashion, her cropped sweaters, dainty knitwear, tailored denim, wool mini-skirts, matching pastel sets, encapsulating hip 90s fashion as if she were a cover girl on contemporary issues of Seventeen and Marie Claire. Friends’ Rachel Green’s style, especially in the show’s earlier seasons, is a girly mixing of peppy varsity style from her cheerleading days in Long Island with urbane cool: dainty tops, thick plaid skirts, waist-tied button-ups, sports logoed sweaters, high-waisted boyfriend jeans, delicately printed mini-dresses, and tennis shoes. Thrifted vintage and handmade preppy pieces are a staple of Queens-raised, working-girl Fran Fine’s kitschy, campy yet uber-stylish wardrobe in The Nanny (1993-1999), including decorated blazers, houndstooth and checkerboard mini-skirts, 1960s matching bright and patterned sets, vibrant turtlenecks, and simple, chic evening dresses.

Taking place between the spotlessly polished surfaces and the debauched underbelly of New York high society, Roger Kumble’s Cruel Intentions (1999) is a star student in the canon of dark academia films. Sarah Michelle Gellar’s cunning and seductive villainess Kathryn Merteuil is an idol of dark femininity and refined, Oxford-influenced prep, being seen in narrow black suits, classic Dior dresses, silver-detailed Gucci bustiers, sheer tops, leather pencil skirts, slinky Versace gowns and layered pearl necklaces. Contrasting Kathryn’s New York-old money family and essence, Reese Witherspoon’s Annette is a Southern belle from Kansas who displays the softer, sweeter facet of preppy: knit tea dresses, lacey summer dresses, fuzzy cardigans, fitted sweaters, all usually in pink or white, light-wash boyfriend jeans and delicate gold jewelry.

In between her hometown of Stars Hollow, her grandparents’ high society in Hartford, Connecticut, and Yale where she attends, Gilmore Girls’ Rory Gilmore chooses casual, romantic outfits that still have a preppy sensibility – romantic jeans, long-sleeve fleece tops, wool sweaters, denim jackets, pastel button-up blouses, and tea-length summer dresses. On the opposite side of the spectrum, Rory’s ambitious, scholastic rival-turned-chosen sister Paris Geller reliably selects fine, timeless, masculine-leaning ensembles including corduroy and leather blazers, collared knitwear, dark dress pants and khaki pants, and leather loafers.

Gossip Girl (2007-2012) is an oft-cited Wonderland of preppy dressing on film, from Blair Waldorf’s classic, regal and European-inspired to Serena van der Woodsen’s feminine and bohemian to Jenny Humphrey’s Vivienne Westwood, rocker-chic takes on the sartorial culture. Park Avenue princess Blair is elegantly fitted blazers, double-breasted trench coats, capelets, pleated and pencil skirts, opaque tights, Mary Jane shoes, delicately printed tea dresses, headbands and pearl jewelry, while free-spirit, wild-child Serena is dainty tank-tops, thin vests, loose cardigans, fitted denim, flowy summer dresses in soft colours, fitted golden and jewel-toned evening gowns, and strappy heels. Over the course of the series, ‘little Jenny Humphrey’s’ style evolves from coquettish button-up blouses, pastel peacoats and pleated skirts to rebellious ripped up denim, motorcycle jackets, micro-miniskirts and plaid slip dresses (as influenced by actress Taylor Momsen’s own style evolution).

In line with the multiplicity of sartorial subcultures present in the 2020s, Gossip Girl (2021-2023) is more experimental with its characters’ fashion, from influencer Julien’s intertwining of American urban streetstyle and varsity prep with oversized letterman jackets, slouchy military jackets, cycling shorts, layered button-ups and cropped sweaters, and crushed velvet thigh-highs, to the literary Audrey’s poised, timeless, Cambridge-inspired bowed, collared blouses, wool vests and cardigans, tweed mini-skirts and dress pants, and heeled leather boots, in neutral colours. The untouchably fashionable Monet de Haan and Luna La take cues from both Blair and Serena, the former’s regal, alpha take on preppy being defined by chunky Chanel blazers and mini-skirts in dark tones, sleek, royal-toned blazers, pin-striped pleated skirts, pastel tweed trench coats, bombshell evening gowns and knee-high leather boots, and the latter’s feminine, romantic take, by Burberry capelets, lacey blouses, cropped, thick-knit sweaters, mini pencil skirts, collared smock dresses and bowed-chokers, in light shades.

Monet and Luna’s trendy and chic approach to upscale dressing is melded with the camp excess of Heathers in Jennifer Kaytin Robinson’s Do Revenge (2022). Besides their uber-preppy and slightly fantastical school uniforms’ lavender and mint sweater-vest and plaid skirt sets, Camila Mendes’ stylish and hardworking Drea sports Cher Horowitz-inspired tube mini-dresses, shimmering, sheer outerwear, and a feather-trimmed, honey-yellow blazer and skirt set, a fuzzy, tweed cardigan and mini-skirt set, a 1970s silk, houndstooth set, fuzzy, pastel, spaghetti-strap tanks, high-waisted checkerboard and pastel shorts, and bold pearl jewelry, and her girl gang at Rosehill Country Day High School wears similarly dramatic, fashion-forward looks. From Tara’s (Alisha Boe) matching white satin blazer and flared pants and matching Versace gold-detailed bando and culottes to Meghan’s (Paris Berelc) 90s Gucci-inspired mini-dress and pink evening gloves and metallic Windbreaker and heart-emblazoned jeans to Montana’s (Maia Reficco) feathered tube-top and satin mini-skirt and candy-coloured sports jacket and pin-striped tube mini-dress, campy contemporary notions of prep are on full display. After a makeover inspired by Tai’s in Clueless, even Maya Hawke’s Eleanor comes into her own indie-kid play on prep with floral-printed overalls, printed turtlenecks, pastel athletic-wear, an earthy, metallic blazer and dress-pants set, a lacey, silver smock-dress, and quirky sun hats.