thigh high boots with hoodie

Over the past two decades, the fashion of the 90s has remained a timeless source of inspiration for both designers and movie enthusiasts. With 90s trends firmly back in vogue, now is the perfect time to revisit some of the decade’s most stylish movie characters. From Cher Horowitz’s iconic yellow plaid ensemble to Mia Wallace’s classic white button-up shirt and The Dude’s cozy Pendleton cardigan, these legendary outfits have influenced countless runway shows and Halloween costumes since they first graced the silver screen over twenty years ago.

ROMEO & JULIET, 1996

The 1996 adaptation of Shakespeare’s iconic tragedy Romeo and Juliet reimagines the classic tale by replacing its traditional Italian countryside setting and Elizabethan costumes with a vibrant seaside town called Verona Beach, complete with Hawaiian shirts. Even if Shakespeare isn’t your usual preference, the poignant romance between a young, charismatic Leonardo DiCaprio and Claire Danes makes it a worthwhile watch for a Friday night.

The film features striking costumes designed by Kym Barrett, the renowned costume designer known for her work on The Matrix trilogy, Cloud Atlas, and Aquaman. Tybalt’s crew, portrayed by John Leguizamo and his gang, wears custom pieces from the now-defunct Dolce & Gabbana diffusion line, inspired by Latin gangs in Los Angeles and Mexico City during the early 90s. In contrast, Romeo and his friends sport unbuttoned Hawaiian shirts, loose cargo pants, worn-out Converse sneakers, and brightly colored hair, perfectly capturing their youthful, rebellious spirit.

DAZED AND CONFUSED, 1993

Dazed and Confused takes us back to a Texas high school in 1976, following a group of lovable hippies on their final day of school. While the film is widely recognized as a breakout role for future stars like Matthew McConaughey, Ben Affleck, Parker Posey, and Milla Jovovich, it’s costume designer Katherine Dover’s keen eye for vintage fashion that truly shines.

The film features a delightful blend of 90s and 70s styles, predominantly showcasing authentic vintage pieces from the era, such as flared jeans, platform clogs, and peasant blouses, all of which remain stylish today. Each character’s distinct personal style signals their clique affiliation and hints at just how many times they’ll indulge throughout the film. So, it goes without saying that we wholeheartedly recommend rolling a joint or two while you enjoy this classic!

FIGHT CLUB, 1999

While the first rule of Fight Club is to avoid discussing it, we’re breaking that rule to shine a light on the film’s iconic costumes. This cult classic follows a nameless narrator (Edward Norton) as he spirals deeper into the chaotic world of soap-maker Tyler Durden (Brad Pitt) and his underground fight club.

The film’s dark narrative and carefully curated costumes reflect its anti-establishment themes and critique of capitalist consumer culture. Tyler’s striking blood-red leather jacket, low-slung pants, and eclectic prints create a stark contrast to the narrator’s ill-fitting suits and Marla Singer’s (Helena Bonham Carter) shabby-chic, dumpster-diving style.

In the twenty-plus years since Fight Club was released, numerous designers have drawn inspiration from its dark satire. Shortly after the film debuted in 1999, Donatella Versace labeled the brand’s Fall 2000 collection as “a Fight Club collection,” although the designs bore little resemblance to the film’s costumes. Additionally, Jean-Paul Gaultier took cues from this cult classic for his Fall 2010 collaboration with Everlast, featuring a boxing-inspired collection complete with mesh tank tops, ringside robes, track pants, and leather jackets.

NEVER BEEN KISSED, 1999

Never Been Kissed wouldn’t be the same without its campy, over-the-top 90s fashion, crafted by the legendary costume designer Mona May. The rom-com follows copy editor Josie Gellar (Drew Barrymore) as she goes undercover as a high school student, reliving the traumas of her own past through a series of flashbacks to her days as “Josie Gross-ie.”

The film’s costumes reflect Josie’s journey from an awkward teenager to a confident young adult. Her exaggerated 80s prom dress and the white feather-trimmed outfit she wears on her first day of school illustrate her struggles to fit in and become someone she’s not. In contrast, her pink lace dress in the final scene signifies her realization of who she truly is, marking her transformation and acceptance of herself.

BASIC INSTINCT, 1992

Basic Instinct embodies all the elements of a thrilling crime drama, featuring steamy encounters, brutal murder, and irresistible 90s style. The film follows detective Nick Curran (Michael Douglas) as he investigates the murder of a former rock star, becoming romantically involved with the primary suspect, the seductive and manipulative novelist Catherine Tramell (Sharon Stone).

While Catherine’s iconic turtleneck dress and white shawl overcoat from the infamous leg-crossing interrogation scene is undoubtedly the standout costume, all of her minimalist 90s outfits are enviably stylish. Costume designer Ellen Mirojnick drew inspiration for the film’s lead characters from the glamorous blonde bombshells and sophisticated suits found in Hitchcock classics like Dial M for Murder, To Catch a Thief, and Rear Window. Catherine’s wardrobe features light colors, relaxed silhouettes, and simple knits, providing a refreshing contrast to the typical skintight black ensembles worn by femme fatale characters in Hollywood.

“I thought the costumes and the look of the film were extremely classic,” Mirojnick remarked in an interview with Clothes on Film. “The contemporary feel of the film is even more relevant today. It is a timeless piece.”

THE BIG LEBOWSKI, 1998

At first glance, The Big Lebowski may not appear to be a fashion triumph, but its relaxed stoner style has achieved legendary status. The film follows “the Dude” (Jeff Bridges), a laid-back slacker who enjoys pot, White Russians, and bowling with his friends as they navigate a high-stakes case of mistaken identity. The Dude’s wardrobe, featuring bowling shirts, jelly sandals, a tattered bathrobe, unkempt long hair, stretched-out t-shirts, slouchy board shorts, and faded zip-up hoodies, perfectly embodies the anti-fashion aesthetic of carefree hippies and middle-aged men in the late 90s and early 2000s.

Over the past two decades, the Dude’s Pendleton Westerly cardigan has become an iconic symbol of the film. Costume designer Mary Zophres explained, “One of the first lines in the 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.” The humble Dude sweater gained such popularity among fans that Pendleton even relaunched it as part of their permanent The Dude’s Collection.

THELMA & LOUISE, 1991

Thelma & Louise follows two best friends on a joyride through the desert as they escape their pasts and elude the police. The film’s straightforward yet impactful costumes, designed by the late Elizabeth McBride, effectively highlight the contrasts between Thelma (Geena Davis) and Louise (Susan Sarandon) while reflecting their personal evolution throughout the narrative. Plus, they help make young Brad Pitt look like an absolute heartthrob.

As the film progresses, both characters’ styles transform from sweet and feminine to tough and masculine as they shed their old lives. Thelma starts off as a naive housewife in frilly white blouses and silky florals, but as she discovers her freedom, her wardrobe shifts to grungy denim, baseball caps, and basic tees. Similarly, Louise trades her waitress uniform for masculine white tees, aviators, and jeans that challenge gender norms, perfectly capturing her tough, rebellious spirit.

ROMY AND MICHELE’S HIGH SCHOOL REUNION, 1997

Romy and Michele’s High School Reunion is undoubtedly one of the ultimate 90s fashion films. This campy comedy follows stylish best friends Romy White (Mira Sorvino) and Michele Weinberger (Lisa Kudrow) as they concoct an elaborate lie to impress their former classmates at their ten-year high school reunion. Kudrow and Sorvino’s playful mini skirts, cherry accessories, sky-high platform heels, and perfectly coordinated outfits define their characters as the quintessential ditzy blondes with enviable 90s style.

As with many iconic 90s films, the costumes were designed by Mona May, the stylist behind other sartorial gems like The Wedding Singer, Clueless, A Night at the Roxbury, and Never Been Kissed. Throughout the film, Romy and Michele undergo nearly 50 outfit changes, showcasing everything from feather-trimmed spandex mini dresses to chic mini skirts and crop tops, and even Madonna-inspired 80s prom ensembles.

PRETTY WOMAN, 1990

Pretty Woman encapsulates everything you could desire from a 90s romantic comedy: love, extravagant shopping sprees, a successful businessman who is both charming and kind, and, of course, Julia Roberts. However, beneath its cliché tropes lies a film that earned Roberts her first Oscar nomination for Best Actress and secured a BAFTA for Best Costume Design for the talented Marilyn Vance.

This modern-day “prince and the pauper” tale follows Vivian Ward (Julia Roberts) as she evolves from streetwalker to Hollywood socialite after encountering millionaire Edward Lewis (Richard Gere). Vivian’s stylish 90s wardrobe beautifully reflects her transformation and serves as a reminder not to judge appearances. “When she meets Richard Gere’s character, she notices how neat and stylish he is, prompting her own wardrobe to become more minimalist,” Vance explained in an interview with Vogue France.

At the film’s outset, Vivian can be seen in a go-go-inspired cut-out mini dress, complete with a newsboy cap and thigh-high boots as she navigates Hollywood Boulevard. A blonde wig conceals her signature red locks, symbolizing her hidden identity during this phase of her life. By the film’s conclusion, Roberts’ natural curls are elegantly cascading down her shoulders, highlighting her stunning off-the-shoulder red opera gown and that iconic necklace—boasting $1.35 million worth of pear-cut rubies set in diamond-encrusted hearts. This outfit perfectly embodies her metamorphosis and remains one of the film’s most unforgettable fashion moments.

POETIC JUSTICE, 1993

Set against the backdrop of a predominantly white film industry in the 90s, Poetic Justice delivers a vital dose of Black Girl Magic while exploring the effects of violence in Black communities. Directed by John Singleton, this film serves as a follow-up to his Oscar-nominated work Boyz n the Hood and follows Justice (Janet Jackson), a hairdresser grappling with the murder of her boyfriend Markell (Q-Tip). As she navigates her grief through poetry, she builds relationships with her friend Iesha (Regina King) and a young postal clerk named Lucky (Tupac Shakur).

The film’s costumes, designed by John Lemons and Sharlene Williams, capture the essence of early 90s Black fashion. Justice’s signature style features long box braids, baggy jeans, crop tops, hoop earrings, sports jerseys, and an oversized newsboy cap, creating a relaxed, homegirl-next-door vibe. This aesthetic not only defines her character but also sets the tone for women’s hip-hop fashion that would resonate for decades to come.

FEAR AND LOATHING IN LAS VEGAS, 1998

Fear and Loathing in Las Vegas, based on Hunter S. Thompson’s 1971 novel, follows Raoul Duke (Johnny Depp) and his companion Dr. Gonzo (Benicio del Toro) on a wild, psychedelic drug-fueled journey to Las Vegas. Thompson famously advised, “The only way to prepare for a trip like this was to dress up like human peacocks and get crazy then screech off across the desert.”

Costume designer Julie Weiss embraced this eccentric vision, meticulously capturing Thompson’s unique personal style—from the plastic cigarette holder to the outrageous vacation outfits. The film features iconic pieces like yellow aviators, Hawaiian shirts, bucket hats, a patchwork cardigan, khaki shorts, and well-worn white Converse Chuck Taylor All-Stars, all of which could easily have been pulled from Thompson’s own closet. In preparation for his role, Depp even lived in Thompson’s basement for four months, during which Thompson personally shaved Depp’s head to fully immerse him in the character.

PULP FICTION, 1994

The 90s cult classic Pulp Fiction weaves together the stories of two mob hitmen, a gangster and his stylish wife, a boxer, and various other criminals in Los Angeles. Critic Roger Ebert famously remarked that it was “either one of the year’s best films or the worst.” Like many Quentin Tarantino films, Pulp Fiction delivers a blend of violence, sharp dialogue, and quirky characters that inspire memorable Halloween costumes. And who could forget the iconic dance scene featuring John Travolta and Uma Thurman?

Costume designer Betsy Heimann drew inspiration from Japanese manga and Tarantino’s earlier film, Reservoir Dogs, to craft the film’s minimalist aesthetic. Mia Wallace (Uma Thurman) embodies a chic yet rebellious spirit in her white button-up shirt and cropped black pants, echoing the simple black suit, long hair, and bolo tie worn by Vincent Vega (John Travolta).

In an interview with Vogue, Heimann explained, “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.”

CRUEL INTENTIONS, 1999

From Kathryn Merteuil’s (Sarah Michelle Gellar) corset dress to Sebastian Valmont’s (Ryan Phillippe) impossibly stylish rimless glasses, the chic costumes in Cruel Intentions perfectly capture the essence of minimalist 90s fashion. This sexy teen drama explores the love triangles and revenge schemes of two step-siblings as they attempt to seduce the new girl at their Manhattan prep school. The film artfully balances innocence and power through its school uniforms and revealing outfits.

Costume designer Denise Wingate, known for her work on 90s classics like Melrose Place, She’s All That, and The Sweetest Thing, aligned each character’s style with their personality. The menacing step-siblings, Kathryn and Sebastian, predominantly wear dark colors, sexy silhouettes, and power suits that reflect their privileged status. In contrast, more virtuous characters like Annette Hargrove (played by a young Reese Witherspoon) and Cecile Caldwell (Selma Blair) sport lighter colors, conservative cuts, and preppy Upper East Side cardigans, highlighting their innocence and naivety. This contrast is famously exemplified in the film’s iconic kiss scene between Sarah Michelle Gellar and Selma Blair, which beautifully underscores this duality.

THE MATRIX, 1999

Like many science-fiction films, The Matrix uses its futuristic costumes to reflect the progressive themes and boundary-pushing social commentary woven throughout its storyline. Costume designer Kym Barrett emphasizes that every element of the film’s monochrome black outfits carries meaning. “It was all about how to create a language that the audience could clue into what we were doing subconsciously,” she explained, also noting her work on the sequels, The Matrix Reloaded and The Matrix Revolutions.

The 1999 film, featuring Keanu Reeves, Carrie-Anne Moss, and Laurence Fishburne, follows computer hacker Neo (Reeves) as he uncovers the truth about a reality manipulated by deceptive cyber-intelligence. The long leather coats, lug-sole boots, and skinny sunglasses encapsulate the anarchist, rebellious spirit of the film’s bullet-dodging heroes. Barrett compares the long leather coats to superhero capes, stating, “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.”

Over the past two decades, The Matrix’s rebellious themes and iconic all-black costumes have continued to inspire designers, celebrities, and fashionable movie buffs alike. John Galliano, for instance, cited being “deeply inspired by The Matrix” when creating the PVC coats and futuristic dresses for Christian Dior’s Fall 1999 Couture collection.

CLUELESS, 1995

When discussing 90s movie fashion, there’s no better starting point than Clueless. This campy coming-of-age story follows Cher Horowitz (Alicia Silverstone) and her partner in crime, Dionne (Stacey Dash), as they give their new friend Tai (Brittany Murphy) a much-needed makeover and help her navigate love. Cher alone sports over 30 different outfits throughout the film, ranging from argyle mini skirts to skimpy red tank dresses and sheer organza button-ups. Despite her casual name-dropping of high-end designers like Alaïa and Calvin Klein, many of the costumes were sourced from malls and thrift shops, thanks to the costume department’s limited budget.

Since its release in 1995, Clueless’s iconic plaid outfits—especially the yellow plaid skirt and blazer Cher selects from her futuristic closet in the opening scene—have cemented their status as some of the most influential movie costumes in fashion history. Over the past two decades, designers from Donatella Versace to Michael Kors have offered their own modern takes on Cher’s 90s style, featuring 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,” stylist Mona May explained in an interview with Vogue.

CONCLUSION

The 90s, a decade of cultural renaissance, left an indelible mark on fashion that continues to resonate today. From grunge to minimalism, the trends that emerged during this time have evolved and reemerged, influencing contemporary styles.

The enduring appeal of 90s fashion lies in its authenticity and rebellion. It was a time of experimentation and self-expression, resulting in iconic looks that captured the spirit of the era. As we look back on these trends, we can appreciate their timeless quality and the impact they have had on modern fashion.

Whether it’s the effortless cool of grunge, the minimalist elegance of slip dresses, or the nostalgic charm of chokers, the 90s fashion legacy continues to inspire designers and fashion enthusiasts alike. The trends of this decade serve as a testament to the cyclical nature of fashion, reminding us that while styles may come and go, the essence of what makes them enduring remains constant.