Preppy Fashion
Illustration by Amelia Wu
Sights | Caitlin Joy
In the 1980s, American brands like Tommy Hilfiger and Calvin Klein brought the fashion of Ivy League campuses into the realm of commercial fashion. Their takes on the preppy style of upper-class institutions sparked an influx of contemporary adaptations amongst young people during the decade.
Michael Lehmann’s Heathers (1986) satirically revels in the pristine poshness of the film’s titular elite high school clique and the shiny croquet-playing suburbs that the clique that 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, starched blouses, jewel-toned fitted blazers, matching knee-length skirts, and Mary Jane shoes. Winona Ryders’ bookish outsider Veronica Sawyer shares in this look, wearing an oversized, patchwork, double-breasted sweater, narrow blazers, powdery button-ups and thick pleated skirts,
Fashion is also a main character in Amy Heckerling’s Clueless (1995), though unlike Heathers, it is a form of autonomy and artistic expression for the Beverly Hills girls at its center, Cher Horowitz and Dionne Davenport. Cher and Dionne’s fashion embodies the classy ethos of preppy dressing, though their garment choices pull this ethos into the glamorous, glossy magazines of the 90s. Alicia Silverstone’s character ‘Cher’ has a style that is ultra-feminine and sweet, with her character wearing soft, pastel collared shirts, plaid, and checkerboard skirts, strappy heels, and her iconic three-piece honey-yellow set. Dionne’s style, portrayed by Stacey Dash, is more high-fashion and cultured, with her character going for bold, edgy plaids (including her iconic three-piece black-and-red set), velvet mini-dresses in royal tones, leather and latex mini-skirts, and statement hats. Even Tai, the sporty transfer student, has her own cool, casual play on preppy fashion by the end of the film, wearing preppy-patterned short-sleeved tops, cropped flannels, 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, and tailored denim, encapsulate hip 90s fashion as if she were a cover girl on contemporary issues of Seventeen and Marie Claire. Rachel Green’s style in the hit sitcom Friends, is a girly mix of peppy varsity style, especially in the show’s earlier seasons. It’s drawn from her cheerleading days in Long Island, featuring dainty tops, thick plaid skirts, waist-tied button-ups, delicately printed mini-dresses, and tennis shoes. In The Nanny (1993-1999), thrifted vintage and handmade preppy pieces are a staple of Queens-raised, working-girl Fran Fine’s kitschy, campy yet uber-stylish wardrobe. Her wardrobe includes decorated blazers, checkerboard mini-skirts,1960s matching bright and patterned sets, 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 exemplar in the canon of dark academia films. The villainess Kathryn Merteuil is an idol of both dark femininity and refined, Oxford-influenced prep, wearing narrow black suits, classic Dior dresses, 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, fitted sweaters, all usually in pink or white, and delicate gold jewelry.
In between her hometown of Stars Hollow, her grandparents’ high society in Hartford, Connecticut, and the prestigious Yale University, where she studies, Gilmore Girls’ Rory Gilmore chooses casual, romantic outfits that still have a preppy sensibility – 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 that include corduroy and leather blazers, collared knitwear, and leather loafers. The dichotomy of these outfits is interesting as both characters are highly academic, striving for the same goal but Paris is presented as a more intense character, and this is cleverly represented through the more serious-business-like outfits.
Gossip Girl (2007-2012) is an oft-cited Wonderland of preppy dressing in the world of film, from Blair Waldorf’s classic, regal, and European-inspired style, to Serena van der Woodsen’s feminine and bohemian look, to Jenny Humphrey’s Vivienne Westwood, rocker-chic takes on the sartorial culture. Park Avenue princess. Over the course of the series, ‘Little Jenny Humphrey’s’ style evolves from coquettish button-up blouses, and pastel peacoats to rebellious ripped-up denim, motorcycle jackets, 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 street style and varsity prep with oversized letterman jackets, and crushed velvet thigh-highs, to the literary Audrey’s poised, timeless, Cambridge-inspired collared blouses, and heeled leather boots, in neutral colours. The untouchably fashionable Monet de Haan and Luna La take cues from both Blair and Serena. Blair’s alpha takes on preppy is defined by chunky Chanel blazers and mini-skirts in dark tones, her signature headbands, sleek, royal-toned blazers, and knee-high leather boots. On the other hand, Serena’s feminine, romantic take includes mini pencil skirts, collared smock dresses, and bowed chokers, in light shades. Despite being best friends both from the Upper East Side, their hometown does not limit them as their styles contradict each other.
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 the lavender and mint sweater-vest and plaid skirt sets of their uber-preppy school uniforms, Camila Mendes’ stylish and hardworking Drea also sports Cher Horowitz-inspired tube mini-dresses, shimmering, sheer outerwear, and a feather-trimmed, honey-yellow blazer and skirt set. 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 to Montana’s (Maia Reficco) feathered tube-top and satin mini-skirt and candy-coloured sports jacket, 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, and an earthy.
Overall, we can see the presence of preppy fashion in American film and television since the style’s popularization in the 1980s. It is really interesting to see the director’s style choice for the characters because while they all portray preppiness, they are so different yet with similar nods. The film and television realm really encapsulated what it would be like if Ivy League Campuses were a fashion statement.