The Movies That Defined 90s Style
Over the past two decades, 90s movie fashion has served as a constant source of inspiration for fashion designers and movie buffs alike. Now that 90s fashion trends are here to stay, there’s no better time than now to revisit the most fashionable movie characters throughout the decade. From Cher Horowitz’s yellow plaid outfit to Mia Wallace’s white button-up shirt to The Dude’s Pendleton cardigan, these iconic 90s movie character outfits have inspired countless runway shows and Halloween costumes they hit theaters twenty-some years ago.
These cult classic films and fashionable movie characters are the definition of 90s style.
Clueless, 1995
When discussing 90s movie fashion, there’s no better place to start than Clueless. The campy coming-of-age story follows Cher Horowitz (Alicia Silvertone) as she and her partner in crime Dionne (Stacey Dash) give their new friend Tai (Brittany Murphy) a much-needed makeover and help her find love. Throughout Clueless, Cher alone sports over 30 different outfits, ranging from argyle mini skirts to skimpy red tank dresses to sheer organza button-ups. Despite her casual name-dropping of designers like Alaïa and Calvin Klein, many of the costumes came from malls and thrift shops thanks to the costume department’s limited budget.
Since the film’s release in 1995, Clueless’ plaid outfits— most notably, the yellow plaid skirt and blazer Cher selects from her futuristic closet in the opening scene— have remained some of the most influential movie costumes in fashion history. Over the past 20-something years, everyone from Donatella Versace to Michael Kors has offered their own modern take on Cher’s 90s style with bright-colored plaid prints, slip dresses, mini skirts, and knee-high socks. “We really wanted to do the plaid because it was the quintessential schoolgirl outfit,” said stylist Mona May in an interview with Vogue.
The Matrix, 1999
Like many science-fiction movies, The Matrix uses its futuristic costumes to reflect the progressive themes and boundary-pushing social commentary that appear throughout the storyline. According to costume designer Kym Barrett, every aspect of the monochrome black outfits in The Matrix have some kind of meaning. "It was all about how to create a language that the audience could clue them into what we were doing subconsciously,” said Barrett, who also costumed the two sequels, The Matrix Reloaded and The Matrix Revolutions.
The 1999 film starring Keanu Reeves, Carrie-Anne Moss, and Laurence Fishburne follows a computer hacker named Neo (Keanu Reeves) as he discovers that life as he knew it was thanks to deceptive cyber-intelligence. The long leather coats, lug-sole boots, and skinny sunglasses reflect the anarchist, f*ck-shit-up mentality of the bullet-dodging rebels in the film. Barrett likens the long leather coats to superhero capes, explaining, "They can move in an almost gravity-defying way. They can jump across buildings; they can almost fly…I wanted to find a modern version of something that could move like a cape, so that's where the coats were born."
Throughout the past two decades, The Matrix’s rebellious themes and infamous all-black costumes remained a constant source of inspiration for designers, celebrities, and fashionable movie buffs alike. John Galliano said he “deeply inspired by The Matrix” when designing the PVC coats and futuristic dresses for Christian Dior’s Fall 1999 Couture collection.
Cruel Intentions, 1999
From Kathryn Merteuil’s (Sarah Michelle Gellar) corset dress to Sebastian Valmont’s (Ryan Phillippe) impossibly sexy rimless glasses, the chic costumes in Cruel Intentions perfectly encapsulate minimalist 90s fashion. The sexy teen drama follows the love triangles and revenge plots of two step-siblings as they attempt to deflower the new girl at their Manhattan prep school. Throughout the film, the school uniforms and revealing outfits play on this balance of innocence and power.
Cruel Intentions costume designer Denise Wingate (who also costumed 90s classics like Melrose Place, She's All That, and The Sweetest Thing) corresponded each character’s style with their personality. Throughout the film, the menacing step-siblings, Kathyrn and Sebastian, wear mostly dark colors, sexy silhouettes, and power suits to showcase their rich-kid status. By contrast, more virtuous characters like Annette Hargrove (played by a young Reese Witherspoon) and Cecile Caldwell (Selma Blair) wear light colors, conservative cuts, and preppy Upper East Side cardigans that reflect their innocence and naivety. No moment in the film highlights this duality better than Sarah Michelle Gellar and Selma Blair’s infamous kiss scene.
Pulp Fiction, 1994
The 90s cult classic Pulp Fiction follows the intertwining stories of two mob hitmen, a gangster and his stylish wife, a boxer, and a handful of other LA criminals in what critic Roger Ebert famously described as “either one of the year’s best films, or the worst.” Like most Quentin Tarantino movies, Pulp Fiction offers plenty of blood, punchy dialogue, and quirky characters that make for easy last-minute Halloween costumes. And who could forget that John Travolta, Uma Thurman dance scene?!
According to costume designer Betsy Heimann, the inspiration behind the film’s minimalist costumes came from Japanese manga and Tarantino’s earlier hit Reservoir Dogs. Mia Wallace’s (Uma Thurman) white button-up shirt, cropped black pants, and sleek bob mirror the simple black suit, long hair, and bolo tie worn by Vincent Vega (John Travolta).
“Mia Wallace: wife of the big boss, tons of money, but inside she’s kind of a bad girl. She wants these guys to like her. She’s totally barred from interacting with any man, so she has a chance to go out one night with Vincent, and she’s like, Well, I’m going to show them I’m a Reservoir Dog like they are,” said Heimann in an interview with Vogue.
Fear and Loathing in Las Vegas, 1998
Fear and Loathing in Las Vegas, adapted from Hunter S. Thompson’s 1971 novel of the same name, follows Raoul Duke (Johnny Depp) and his sidekick Dr. Gonzo (Benicio del Toro) on a psychedelic drug-fueled trip to Las Vegas. “The only way to prepare for a trip like this,” Thompson wrote, “was to dress up like human peacocks and get crazy then screech off across the desert.”
For the movie’s off-beat vacation style, costume designer Julie Weiss channeled the writer’s eccentric personal style right down to the plastic cigarette holder. Fear and Loathing in Las Vegas’ yellow aviators, Hawaiian shirts, bucket hats, patchwork cardigan, khaki shorts, and beat-up white Converse Chuck Taylor All-Stars could easily have come straight from Thompson’s closet. Thompson even let Depp live in his basement for four months to prepare for the role and personally shaved Depp’s head before filming.
Poetic Justice, 1993
Amidst the predominately white movie industry of the 90s, Poetic Justice provided a much-needed dose of Black Girl Magic and shed light on the impacts of violence in Black communities. Directed by John Singleton, the follow-up to the 1991 Oscar-nominated film Boyz n the Hood follows Justice (Janet Jackson), a hairdresser grieving the murder of her boyfriend Markell (Q-Tip), as she processes her grief through poetry and her relationships with her friend Iesha (Regina King) and a young postal clerk named Lucky (Tupac Shakur).
The film’s costumes, courtesy of costume designers John Lemons and Sharlene Williams, are a timestamp of Black fashion in the early 90s. Justice’s long box braids, baggy jeans, crop tops, hoop earrings, sports jerseys, and oversized newsboy cap have a laid-back, homegirl next door vibe that set the tone for women’s hip-hop fashion throughout the decades since.
Pretty Woman, 1990
Pretty Woman has everything you could ask for in a 90s rom-com: love, shopping sprees, a successful businessman who’s miraculously both hot and a decent person, and Julia Roberts. But don’t let the cliché tropes fool you, Pretty Woman earned Roberts her first Oscar nomination for Best Actress and won Marilyn Vance a BAFTA for Best Costume Design.
The prince and the pauper-style love story follows Vivian Ward (Julia Roberts) as she transforms from streetwalker to Hollywood socialite after meeting millionaire Edward Lewis (Richard Gere). Vivian’s chic 90s outfits mirror her metamorphosis and remind viewers that you can’t judge a book by its cover. “When she meets Richard Gere's character, she sees how neat and stylish he is and her own clothes start to get more minimalist," said Vance in an interview with Vogue France.
Early in the film, Vivian sports a go-go style cut-out mini dress with a newsboy cap and thigh-high boots as she picks up men along Hollywood Boulevard. A blonde wig hides her long red hair, shielding her true identity while she works the streets. In the final scene, Roberts’ signature curls are on full display, cascading down her shoulder to showcase her off-the-shoulder red opera dress and that necklace ($1.35 million worth of pear-cut rubies set in diamond-encrusted hearts, in case you were wondering).
Romy and Michele's High School Reunion, 1997
Romy and Michele’s High School Reunion is undoubtedly one of the best 90s fashion movies out there. The campy comedy follows two stylish BFFs, Romy White (Mira Sorvino) and Michele Weinberger (Lisa Kudrow) as they create an elaborate lie to impress their former classmates at their ten-year high school reunion. Kudrow and Sorvino’s girly mini skirts, cherry accessories, sky-high platform heels, and coordinating outfits distinguish their characters as stereotypical ditsy blondes with enviably good 90s style.
Like most 90s fashion movies, Romy and Michele’s High School Reunion was costumed by Mona May, the stylist behind sartorial masterpieces like The Wedding Singer, Clueless, A Night at the Roxbury, and Never Been Kissed. Throughout the movie, Romy and Michele have close to 50 outfit changes, ranging from feather-trimmed spandex mini dresses to mini skirts and crop tops to Madonna-inspired 80s prom outfits.
Thelma & Louise, 1991
Thelma & Louise follows two best friends on a joyride through the desert as they escape their pasts and evade the police. The film’s simple but impactful looks, costumed by the late Elizabeth McBride, highlight the nuances between Thelma (Geena Davis) and Louise (Susan Sarandon) and mirror their evolution throughout the storyline. Not to mention, they make young Brad Pitt look like an absolute snack.
Over the course of the film, both characters’ style shifts from sweet and feminine to tough and masculine as they leave their everyday lives behind. While Thelma begins the story as a sweet, naive housewife in frilly white blouses and silky florals, her style shifts towards grungy denim, baseball hats, and basic tees as she finds her freedom. Similarly, Louise ditches her waitress uniform for masculine white tees, aviators, and jeans that defy gender stereotypes and embody her tough, rebellious attitude.
The Big Lebowski, 1998
While The Big Lebowski may not seem like a sartorial success at first glance, its laid-back stoner style has become the stuff of legends. The film follows “the Dude” (Jeff Bridges), a pot-smoking, White Russian-drinking slacker and his bowling buddies as they resolve a high-stakes case of mistaken identity. The Big Lebowski’s bowling shirts, jelly sandals, tattered bathrobe, unkempt long hair, stretched-out t-shirts, slouchy board shorts, and faded zip-up hoodies perfectly capture the anti-fashion look of unbothered hippies and middle-aged men in the late 90s and early 2000s.
Over the past twenty years, the Dude’s Pendelton Westerly cardigan has become synonymous with the film. “One of the first lines in this script describes the Dude as ‘terminally relaxed.’ That says a lot! So I decided the Dude would wear a lot of elastic waists so he doesn’t have to bother with buttons; he never wears a button-down shirt either, just things that pull over his head and a lot of knits,” said costume designer Mary Zophres. In fact, the humble Dude sweater garnered so much attention from fans that Pendleton relaunched the style in their permanent The Dude’s Collection.
Basic Instinct, 1992
Like any good lusty crime drama, Basic Instinct is loaded with steamy sex, violent murder, and drool-worthy 90s style. The story follows detective Nick Curran (Michael Douglas) as he investigates the murder of a former rock star and becomes romantically entangled with the main suspect, a seductive and manipulative novelist Catherine Tramell (Sharon Stone).
While her turtleneck dress and white shawl overcoat from the infamous leg-crossing interrogation scene is undeniably the best costume in the film, all of Catherine’s minimalist 90s outfits are enviously good. Costume designer Ellen Mirojnick drew inspiration for Basic Instinct’s lead characters from the blonde bombshells and deceivingly put-together suits in Hitchcock films like Dial M for Murder, To Catch a Thief, and Rear Window. Catherine wears light colors, loose cuts, and simple knits to contrast the stereotypical skintight black outfits of femme fatale characters in Hollywood.
“I thought the costumes and the look of the film were extremely classic,” said Mirojnick in an interview with Clothes on Film. “The contemporary feel of the film is even more contemporary today. It is a timeless piece.”
Never Been Kissed, 1999
Never Been Kissed just wouldn’t be the same without its campy, over-the-top 90s fashion courtesy of legendary 90s costume designer Mona May. The rom-com follows copy editor Josie Gellar (Drew Barrymore) as she goes undercover as a high school student and relives the horrors of her own high school experience through a series of flashbacks to her days as “Josie Gross-ie.”
The costumes throughout Never Been Kissed reflect Josie’s journey as she matures from an awkward teenager to a self-assured 20-something. While her exaggerated 80s prom dress and white feather-trimmed first day of school outfit reveal her attempts to become someone she’s not, her pink lace dress in the final scene confirms she’s finally discovered who she really is.
Fight Club, 1999
Though the first rule of fight club is not to talk about fight club, we’re skirting the rules to highlight the cult classic movie’s iconic costumes. Fight Club is a nihilistic film that follows a nameless first-person narrator (Edward Norton) as he plunges further and further into the dangerous world of soap-maker Tyler Durdan (Brad Pitt) and his underground fight club.
Fight Club’s dark narrative and meticulously selected costumes reflect the film’s anti-establishment themes and social commentary on capitalist consumer culture. Tyler’s blood-red leather jacket, low-slung pants, and eclectic prints stand out in stark contrast to our nameless narrator’s ill-fitting suits and Marla Singer’s (Helena Bonham Carter) dumpster-diving, shabby-chic style.
In the twenty-some years since Fight Club hit theaters, countless designers have turned to the dark satire for fashion inspiration. Shortly after the film’s release in 1999, Donatella Versace dubbed Versace’s Fall 2000 collection, “a Fight Club collection,” though we’ll admit the looks in no way resembled the costumes in the film. And for his Fall 2010 collaboration with Everlast, Jean-Paul Gaultier drew inspiration from the cult classic for his boxing-inspired collection of mesh tank tops, ringside robes, track pants, and leather jackets.
Dazed and Confused, 1993
Dazed and Confused is set at a Texas high school in 1976 and follows a crew of lovable hippies on their last day of school. While the teen stoner movie is best known as being a breakout role for soon-to-be stars like Matthew McConaughey, Ben Affleck, Parker Posey, and Milla Jovovich, it’s costume designer Katherine Dover’s impeccable eye for vintage clothes that really steal the show.
The flick’s 90s-meets-70s style is comprised almost entirely of authentic vintage clothing from the era, including flare jeans, platform clogs, and peasant blouses that are undeniably relevant today. Each character’s unique personal style cues viewers in on which clique they belong to and how many times they’ll get baked throughout the movie. Needless to say, we 100% recommend rolling a joint or two while you watch.
Romeo & Juliet, 1996
The 1996 version of Shakespeare’s famous tragedy Romeo and Juliet swaps the play’s traditional Italian countryside setting and Elizabethan era costumes for Hawaiian shirts and a fictional seaside town called Verona Beach. Even if Shakespeare isn’t your thing, the heartbreaking romance between a hunky young Leonardo Dicaprio and Clare Danes is well worth a few hours on a Friday night.
The film’s notorious costumes were styled by Kym Barrett, the legendary costume designer behind The Matrix trilogy, Cloud Atlas, and Aquaman. Tybalt’s (John Leguizamo) entire crew wears custom-made DG, the now-defunct Dolce & Gabbana diffusion line, modeled after Latin gangs in LA and Mexico City during the early 90s. By contrast, Romeo and his gang sport unbuttoned Hawaiian shirts, baggy cargo pants, beat-up Converse, and colored hair that embody their youthful, rebellious attitudes.
