True style is rooted in authenticity. The most stylish movies recognize that and are cherished because of it. They offer more than just wonderful scenes to reference. Our favorite on-screen wardrobes capture how style can transform the course of a character’s life and help define a moment in time.
In the post-Challengers era, we’ve encountered thematic press-tour looks that blur lines between actor and character, as well as strategic, shoppable film-inspired collaborations. We’ve also gained the ability to quantify our nostalgia, like search spikes for Leeloo-inspired costumes around Halloween.
Not all great movies are stylish, but all stylish movies are great. These are the 20 that we think exemplify that the best.
Style: Authentic ’90s skater
Costume Designer: Heidi Bivens
Raw, nostalgic, and gritty—that’s the perfect way to describe Jonah Hill’s 2018 film Mid90s. It’s a coming-of-age story that captures the essence of ’90s skate culture in Los Angeles, down to the wardrobe. The outfits in the film feature oversized tees, baggy denim, DC shoes, Vans, and iconic ’90s skate brands like World Industries and Blind. You know you’re watching a great film when it feels like you’ve been transported into the era it’s set in, and Mid90s does exactly that. Skate culture and its style grew more popular over the years—not because skaters set out to be fashionable, but because they were effortlessly cool. In the most beautiful, carefree, and rugged way, skaters have become a major influence on both streetwear and high fashion. Mid90s leans into the simplicity and authenticity of that style.
While every character in Mid90s shares a similar aesthetic, F*cksh*t is by far the flyest in the film. His long blonde hair, playful energy, and larger-than-life persona make him one of the coolest characters, but his outfits stand out the most: peep the Menace Skateboards’ “Enter The Pu-Tang” and Cypress Hill “The Phuncky” T-shirts. While the film is a tribute to the ’90s, the overall style remains just as popular today. –Bree Walker
Style: Worn-in Hollywood grit
Costume Designer: Arianne Phillips
If aspiration had a look, it would be actor Rick Dalton’s (Leonardo DiCaprio) cowboy boots and Steve McQueen-inspired medallion necklace that reflect his struggle to maintain his Western star image. If confidence were an outfit, it would be Dalton’s stuntman Cliff Booth’s (Brad Pitt) effortless Wrangler Canadian tuxedo. Margot Robbie’s rendition of Sharon Tate wears fur coats and black go-go boots, paired with the real Tate’s jewelry, which adds an authenticity and warmth to the ’60s period film. Western motifs also play an integral role in the styling through Bounty Law and Lancer, the intra-movie television shows in which Dalton star. Aged leathers, fringe, and oversized belt buckles ground the film’s Hollywood cowboy aesthetic. The faithfulness to the time period extends to details like Cliff’s Champion ringer tee and a selection of other clothing only from brands active in the ’60s and ’70s. Even the Manson Family’s patchwork denim avoids cliché tie-dye, opting instead for an authentic-yet-subtle counterculture vibe. This careful styling enhances storytelling, capturing the essence of the era without relying on obvious visual shorthand. –Maya Kotomori
Style: Aspirational excess
Costume Designer: Patricia Norris
Sunshine, plastic, sequins, machine guns—1980s Miami is not just represented, but canonized in Brian De Palma’s Scarface through costume designer Patricia Norris’ vision. We see kingpin-in-training Tony Montana (Al Pacino) earn his status in the transition from his loose-fitting guayaberas to ritzy white suits with wide lapels unbuttoned to show his gold chains. There has perhaps never been a better on-screen cocktail dress than Elvira Hancock’s (Michelle Pfeiffer) dramatic deep V-line halter dress covered in gold sequins, a garment bearing the mark of iconic American designer Roy Halston. He was an early champion of the “less is more” philosophy, whose chic and scantily clad followers (also known as “Halstonettes”) defined the glitzy haze of Studio 54 and inspired Elvira’s high-rolling slinky look. Even the supporting characters reflect the film’s gaudy yet magnetic aesthetic, from Manny’s (Steven Bauer) unbuttoned silk shirts to Frank Lopez’s (Robert Loggia) sharp pinstripe suits, reinforcing the era’s obsession with excess, and foretelling each characters’ ambition, indulgence, and eventual downfall. –Maya Kotomori
Style: Retro futurism
Costume Designer: Hardy Amies
Stanley Kubrick’s 2001: A Space Odyssey is widely regarded as one of the most influential films in cinematic history. It redefined the visual language of science fiction. Its costume design—created by British tailor, couturier, and Queen Elizabeth II’s dressmaker Hardy Amies—translates Kubrick’s futuristic vision into clothing. The uniforms and color-coded spacesuits draw from the space-age aesthetic and the minimalist mod movement of 1960s London. The tailored silhouettes and geometric forms mirror the futuristic themes explored by designers like Pierre Cardin and André Courrèges at the time. The film’s influence can still be seen in designers like Raf Simons in his Fall/Winter 2021 collection, exemplifying how cinema and fashion intersect. –Shinnie Park
Style: ’90s hip-hop
Costume Designer: Donna Berwick
Director Ernest Dickerson’s Harlem coming-of-age movie is as cinematically deep as it is sartorially specific. Bucket hats, light wash denim-on-denim, and headphones set the tone for the story of four friends—Quincy “Q” Powell (Omar Epps), Raheem Porter, Roland Bishop (Tupac Shakur), and Eric “Steel” Thurman—on a perpetual journey for power and respect in the concrete jungle of New York City. The film’s opening scene is a montage of the four teens getting ready for school, each with their own take on the ’90s hip-hop style that underscores the film: Q puts on a floppy orange bucket hat and headphones; Raheem, a form-fitting white tee to show off his muscles; Steel, a pattern-clashing pair of red plaid dungarees and a mime-like black and white striped turtleneck; and Bishop, a simple navy bomber jacket with his signature AR-15 medallion, dangling from a gold chain, peeking out. With a heavy hip-hop influence (the film is Tupac’s acting debut) and cameos from legends like Queen Latifah, gold chains and oversized cargo jackets aren’t just signifiers of clout or nifty tools for smuggling vinyl out of record stores, but garments representative of a lifestyle—a dedication to chasing cool. From a style perspective, the juice is worth the squeeze. –Maya Kotomori
Style: Sportswear chic
Costume Designer: Jonathan Anderson
This spicy tennis flick isn’t only an ode to the sweaty spirit and occasional homoeroticism of competitive tennis through director Luca Guadagnino’s lens, but it’s also fashion designer JW Anderson’s first foray into designing movie costumes. Detail-oriented wardrobe propels the story, with Anderson bringing his avant-garde, deconstructed aesthetic to the world of high-stakes tennis. His costumes blur the lines between performance wear and streetwear, injecting the film with an off-court cool that mirrors tennis’ growing influence in fashion (see: Art’s “I Told Ya” T-shirt., inspired by John F. Kennedy’s 1961 presidential campaign slogan “I Told You So,” later produced and sold by Loewe). Anderson’s 2023 collab with Uniqlo and Roger Federer set the stage for this, proving he knows how to fuse functionality with his signature subversiveness. In Challengers, tennis whites get a remix through cropped silhouettes, asymmetry, and hyper-modern takes on preppy staples. Tracksuits feel runway-ready, and match-day fits have the effortless attitude of something you’d see courtside at the US Open—or in a French showroom. It’s tennis-core-turned-high fashion, perfectly mirroring the film’s tension and sensuality. –Maya Kotomori
Style: Heroin-chic
Costume Designer: Rachael Fleming
It’s hard to judge whether Kate Moss or Trainspotting was the stronger influence in the heroin-chic movement. Not bad for some junkies, who, at best, wiggled through Scotland’s sewage system in ultra-skinny jeans and fried out in bizarre, yellow-tinted sunglasses. Bony, angular bodies are the ideal canvas for showing male midriff or draping retro-ish collared shirts. Renton’s (Ewan McGregor) ragged uniform carries him through the life cycle of drop-outs—he runs in Adidas Super Sambas, then spiffs them up for an inevitable court date. This ragtag cast laid a foundation for normcore. Its impact can still be felt to this day, from the streets to the runways. –Kirsten Chen
Style: Restrained sensuality
Costume Designer: William Chang
In the Mood for Love is as much a visual poem as it is a story of unspoken desire, with its costume design serving as a key narrator of emotion. The costume design was done by William Chang, who has worked with director Wong Kar-Wai on many other productions, including Chungking Express, Happy Together, and 2046. In the film, Su Li-zhen (Maggie Cheung) wears a total of 23 different Qi Paos (aka cheongsams), a high collar, form-fitting dress traditionally worn by Chinese women. Each reflect her shifting emotions and restrained relationship with Chow Mo-wan (Tony Leung). The cheongsams subtly shift from delicate florals and soft pastels in moments of vulnerability to bold, rich hues as Su’s emotions intensify. The dresses evoke both the glamour of 1960s Hong Kong and the societal constraints placed upon her character. –Shinnie Park
Style: Central European kitsch
Costume Designer: Milena Canonero
From the royal purple bellhop uniforms to Willem Defoe’s multi-compartment biker jacket, Wes Andersen’s Grand Budapest Hotel presents a host of fashion confections as sweet as the tiny desserts from Mendl’s. Costume designer Milena Canonero is not just a three-time Academy Award winner, but a longtime collaborator of Andersen, known for bringing his highly specific kitschy style to life with character-defining wardrobe moments—like protagonist Zero Moustafa’s pillbox hat with “Lobby Boy” printed ostentatiously on its front, or jailbird Ludwig’s prison tats, inspired by iconic flaneur Père Jules in French classic L’Atalante (1934). Every character is in a uniform: the deep purple suits worn by helpful Grand Budapest staff, the high-rise trousers jingling with keys and billy clubs worn by encroaching Lutz police officers, or the dark lacy funeral frocks of the up-to-no-good Desgoffe und Taxis sisters. From reference to execution, Canonero’s costuming in Grand Budapest Hotel makes the idiosyncratic fictional world of Zubrowka come to life in all its whimsy. –Maya Kotomori
Style: Elegant impracticality
Costume Designer: Edith Head and Hubert de Givenchy
Oscar-winning costume designer Edith Head and Hubert de Givenchy designed Audrey Hepburn’s wardrobe in Breakfast at Tiffany’s. The actress’ “little black dress” will live on until the end of time as one of the most iconic looks in cinema history. The rest of the film is revered for its most impractical, city-chic moments like swinging earplugs under an eye-lashed sleep mask and eating a croissant in satin opera gloves. The styling expertly defies cinematic taboos. Holly Golightly’s character development starts while she’s in an unfinished, pantless state. Her plain cocktail dress is repeated, but re-accessorized for different impact throughout the movie’s runtime. For those with an indifference to high society, Golightly also dons classic staples like cropped jeans and a trench coat when facing all of life’s woes. –Kirsten Chen
Style: Unrivaled basketball grails
Costume Designer: Francine Jamison-Tanchuck
A telltale sign of the strength within White Men Can’t Jump’s costuming lies in its ability to propel the film’s real, on-court humor. There are obvious cultural and societal nuances of why Woody Harrelson’s outfits are an easy dig for Wesley Snipes, but the player-on-player, clothing-related trash talk really transports audiences to Venice Beach in the ’90s. Bonus points for the extra deep, stretched-out tank tops, decade-defining printed shorts, and cycling caps that appear on Sidney Deane and Billy Hoyle. Sneaker grails like the Air Jordan 6 “Black Infrared” and Nike Air Command Force fly under the radar as the characters’ training garb. –Kirsten Chen
Style: ’90s skate rat
Costume Designer: Kim Marie Druce
Larry Clark’s cult classic was a raw snapshot of the teenage skate rats navigating the Lower East Side in the ’90s. It wasn’t trying to wow us with its wardrobe. It was impactful because it was real. The cast was actual Manhattan kids. This is what they actually wore everyday. The boys skate through the city in super baggy khaki pants you could fit a 40 in, tall tees from popular skate brands like Independent, Ralph Lauren polos, and tops from upstart shops like Supreme (a 2015 collab with the streetwear titan has probably helped bolster Kids’ style cred). Chloe Sevigny’s pixie cut, blue jeans, and cropped ringer tees made her a fashion “it” girl, a title she still holds to this day. A lot of the gear worn in the 90-minute movie is what you still might see the youth rocking if you spent an afternoon in LES today. The style cues have remained relevant through what we now refer to as streetwear. –Mike DeStefano
Style: High-school shopping addict
Costume Designer: Mona May
Stepping away from the popular grunge styles of the ’90s, Clueless presents a guide on ruling your teenage years instead of blending in with your peers. Led by the lovable Cher Horowitz (Alicia Silverstone), the queen bee’s wardrobe is an education on how teens can reference runway-inspired looks while staying true to age-appropriate cuts. When you’re a (fashion) virgin, Clueless wins for sartorially capturing adolescent experiences– surveying schoolyard archetypes, dabbling in rave culture, and confidently strutting in the perfect, preppy first-day-of-school outfit. Once you’re, like, totally indoctrinated, you’ll never stop quoting the designers labels woven into its dialogue: “It’s an ALAÏA!” –Kirsten Chen
Style: The wise guy’s wardrobe
Costume Designer: Richard Bruno
As Henry Hill climbs the ranks of the Italian mafia, he also goes through quite the style evolution in this Martin Scorsese classic. The film spans three decades, from 1955 to 1980, and costume designer Richard Bruno depicts each era to perfection. In that span, we see Hill, played by the late legend Ray Liotta, cycle through a variety of quintessential ensembles of a made man. A gray silk suit and some alligator loafers showcase peak gangster elegance. Buttery leather jackets, a staple in any respectable mobster’s closet, are worn by Hill when it’s time to handle business (no blood stains to speak of though, impressive). There’s a blue striped knit so good it’s been replicated by brands many times over since its brief-but-memorable silver-screen debut. Hill kept it casual by pairing it with a white tank top and gold crucifix chain. We even see Hill don a classic Adidas tracksuit at one point in the film, a look that’s become a staple in many Italian American closets. Tommy and Jimmy’s array of clean suits with giant pointed collars and plaid blazers add to the stellar style, but Hill steals the show. –Mike DeStefano
Style: Modern Elizabethan
Costume Designer: Kym Barrett
Baz Luhrmann’s Romeo + Juliet is celebrated for its contemporary reinterpretation of Shakespeare. Costume designer Kym Barrett was instrumental in crafting a look that resonated with modern audiences, while nodding to the Old English stage play. Barrett approached the film by melding present-day ready-to-wear with subtle Elizabethan cues. Leonardo DiCaprio’s wedding suit was famously custom-made by Prada and Claire Danes’ gown was embroidered with hidden excerpts of Shakespeare’s verse.
Barrett’s vision extended beyond bespoke pieces to include collaborations with top fashion houses. The Capulet boys’ waistcoats and cowboy belts were from Dolce & Gabbana, while the mob bosses and their wives were dressed in Yves Saint Laurent’s signature tailored looks for the film. The rest of the costumes were made in-house by Barrett’s team, who hand-painted every detail on DiCaprio’s iconic Hawaiian shirt. –Shinnie Park
Style: Sci-fi couture
Costume Designer: Jean Paul Gaultier
Luc Besson’s The Fifth Element isn’t just a sci-fi masterpiece—it’s a visual feast of futuristic fashion, brought to life by the visionary Jean-Paul Gaultier. Known for his bold, boundary-pushing designs, Gaultier crafted over 1,000 costumes for the film that merged haute couture with sci-fi spectacle.
Leeloo’s iconic bandage ensemble transforms medical gauze into a daring, avant-garde look, while Ruby Rhod’s leopard-print jumpsuits radiate pure Gaultier energy—flamboyant, theatrical, and impossible to ignore. Even the police uniforms bear his unmistakable touch, featuring mesh, vinyl, and fetish-inspired details that make the future feel as stylish as it is chaotic.
Beyond their striking aesthetics, the costumes serve a deeper purpose: world-building. Gaultier’s designs make the 23rd century feel tangible, ensuring each character looks like they belong in this vibrant, futuristic society. Despite their high-fashion edge, they never feel like artificial creations; they feel like real clothing worn by real people navigating their daily lives. From Korben Dallas’s rugged orange tank top to the hyper-stylized flight attendant uniforms, each piece fits seamlessly into its surroundings. It makes the film’s future vision feel authentic rather than exaggerated.
More than 25 years later, The Fifth Element remains a cult sci-fi classic, but it’s also a lasting fashion statement—one that still feels fresh, daring, and ahead of its time. –Jamal Desroches
Style: Editorial elitism
Costume Designer: Patricia Field
The Devil Wears Prada is what happens when you put the mastermind behind Sex and the City’s wardrobe, Patricia Field, to work on a fashion movie. Andy Sachs (Anne Hathaway) starts off drowning in lumpy cerulean sweaters, because, as Miranda Priestly (Meryl Streep) reminds us, “It’s not just blue, it’s not turquoise, it’s not lapis—it’s actually cerulean.” Her wardrobe evolution tracks her transformation from someone who didn’t take fashion seriously to someone indoctrinated by it.
Then, there’s Priestly asserting her dominance in perfectly tailored Prada suits. She glides, delivering icy glares and deep-cut one-liners like, “That’s all.” Field stretched a $100,000 budget into a $1 million wardrobe, calling in industry favors to pack the film with archival designer pieces. –Shinnie Park
Style: Luxurious ’90s streetwear
Costume Designer: June Ambrose
The three-minute intro to Belly is one of the most visually iconic sequences in hip-hop film history, and the movie itself is arguably one of the greatest style films ever created. A cult classic, Belly was directed by legendary music video director Hype Williams, known for his visually striking aesthetic. The film’s wardrobe heavily reflects late ’90s hip-hop fashion, seamlessly blending streetwear with high-end luxury. From Nas’ black leather Evisu trench coat and pants, white Avirex jacket, and Paolo Gucci sunglasses to Method Man’s bright yellow Avirex leather, Belly redefined how Black culture is represented in both fashion and cinema. Other notable brands featured include Enyce, Eckō, Timberland, Versace, Carhartt, and Phat Farm. June Ambrose, the film’s costume designer, created looks so culturally influential that they continue to inspire brands and designers today.
The beauty of Belly extends beyond clothing; Williams’ signature visual aesthetic, combined with elements like leather furniture and black-and-white prints from French photographer Thierry Le Gouès, elevated the film into a true cinematic masterpiece. Its influence is still evident today, referenced in our era by brands like Supreme (Fall/Winter 2021 collection) and Joe Freshgoods (New Balance 990v4 collection from 2023). Despite being released 27 years ago, Belly has proven to be more than just a film—it is a lasting symbol of Black culture that continues to transcend generations. –Bree Walker
Style: A timeless summertime blueprint
Costume Designer: Ruth E. Carter
This classic Spike Lee joint is rife with memorable style moments. The classic Nike footwear might be the most noteworthy aspect, from Mookie’s “Medicine Ball” Air Trainer 3s to the iconic Buggin’ Out’s scuffed “White Cement” Air Jordan 4s. It’s easy to see why the film has become ingrained in modern sneaker culture.
It isn’t just the shoes. Side characters sport jerseys showing love to the era’s superstar athletes, like Larry Bird and Magic Johnson. Mookie spends half the movie in a throwback Jackie Robinson Dodgers jersey, which doubles as a nice nod to the film’s location and its powerful messaging about race relations in America. Accessories like Radio Raheem’s “Love” and “Hate” four-finger rings or Buggin’ Out’s circular glasses stay etched in your memory. Countless other characters wore era-defining pieces like vibrant tank tops, knee-length shorts covered in bold patterns, and cycling caps in every color. It was a perfect culmination of Brooklyn street style in the ’80s, but the looks have stood the test of time. If you go outside on a sweltering summer day, you’ll still see these outfits. Now, they aren’t just limited to one of the five boroughs. They’re worldwide. Do the Right Thing played a major role in introducing them to the masses. –Mike DeStefano
Style: Unmatched opulence
Costume Designer: Rita Ryack and John A. Dunn
There aren’t many cities more extravagant than Las Vegas. Ace Rothstein’s wardrobe in Casino effortlessly matched that energy to teleport us back to Sin City in the ’70s and ’80s. The mobster played by Robert De Niro appears on screen in over 50 different suits that span every color imaginable, from flamingo pink to shamrock green. After all, Vegas is about excess, right? Louis Vuitton luggage and Carrera shades accentuate each look. Even Rothstein’s silk house robes ooze opulence. And we cannot talk about Casino without mentioning the luxurious looks of Rothstein’s wife Ginger McKenna, played by Sharon Stone, that include chinchilla furs, shimmering gold gowns from Bob Mackie, and an ice blue leather set from Courrèges that’s been a mainstay on women’s fashion moodboards for the past 30 years. It is all accessorized with breathtaking gold and diamonds, courtesy of Cartier, Bulgari, and Van Cleef. Martin Scorsese reportedly gave costume designers Rita Ryback and John A. Dunn $1 million to achieve their vision, and they spared no expense. The gamble paid off. Casino hit the style jackpot. –Mike DeStefano
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