James Bond probably thought he’d cornered the market on fashionable ultra-spies — that is, until Lorraine Broughton came along. The MI6 agent, played with ass-kicking excellence by a platinum-blond Charlize Theron, dominates the masculine world of Cold War Berlin dressed in sky-high stilettos, sharply tailored trench coats, oversize sunglasses, and dramatic leather gloves, by fashion heavy-hitters like John Galliano and Margiela. (The cars, weaponry, and set pieces are also stunning, for those who are into that sort of thing.) —Seija Rankin
“Even reading a script, I picture the jacket first,” says Drive costumer Erin Benach. Consider Ryan Gosling’s custom satin bomber her proof of concept. The garment took her and the star months to perfect. Benach remembers day one of shooting, when the camera panned up the nameless driver’s back to reveal the embroidered scorpion: “I was like, ‘Oh, this is gonna be a thing.’” —Marcus Jones
Costume designer Theadora Van Runkle shaped Faye Dunaway’s Bonnie Parker look with tweed, Norfolk jackets, and V-neck sweaters — ancestors of today’s menswear-inspired trends. To top it off, Bonnie’s beret became the accessory du jour. In the French village shops where the hats originated, sales soared from 5,000 to 12,000 per week. —Lauren Huff
There’s something so fantastically extra about the clothes in a Pedro Almodóvar movie. The color! The exuberance! The polka dots! Breakdown’s women may be on the verge of madness, but they won’t go down without a fight — or a well-structured bustier. Hot pink, leopard prints, stripes, spandex, even a pair of earrings shaped like tiny coffee pots: It’s all outrageously ’80s, and perfectly Pedro. —Leah Greenblatt
Spike Lee’s first feature She's Gotta Have It follows Nola (Tracy Camilla Johns), a sexually liberated artist in Fort Greene. What she and her cohorts wear — high-waisted denim, boxy button-downs, statement accessories — may not seem groundbreaking today, but their enduring ubiquitousness is a testament to a Brooklyn-bred look that has since become the normcore hipster uniform the
world over. —Clarissa Cruz
The precociously stylish teens in the John Hughes classic Pretty in Pink were just so damned assured in their fashion choices: Duckie (Jon Cryer) with his bolo ties and artfully rolled sleeves, Blane
(Andrew McCarthy) with his expensively slouchy suits. And then there’s Andie (Molly Ringwald), whose eclectic style — vintage cardigans, costume jewelry, and florals, florals everywhere — is as enviable now as it was 34 years ago. —CC
Even so early in her dynamic career, Madonna was already delivering master classes on the fine art of reinventing yourself. As the title character in Susan Seidelman’s comedy, wielding a hatbox full of thrifted treasures and chaotically layering mesh over lace and religious pendants over lingerie, the pop icon embodies an edgy liberation fantasy for Rosanna Arquette’s yuppie housewife Roberta (not to mention the film’s Reagan-era audience). In Susan’s hip city-kid world, Roberta finally finds the person she’d always been desperately seeking — herself. But so much better dressed. —Mary Sollosi
Elvira Hancock (Michelle Pfeiffer), the love interest of drug kingpin Tony Montana (Al Pacino), had the slinkiest of uniforms: low-cut, spaghetti-strapped, made of fabrics that render undergarments utterly meaningless. Add the coolest blond bob in movie history, and her silhouette of choice is as minimalist and devastatingly chic as the ’80s were not. —CC
Todd Haynes’ dazzling ode to glam rock is a mad fever dream of glitter bombs and (Ziggy) stardust: spangles and satin, fringe, feather boas, and pants so fitted they’re practically X-rays. Costume designer Sandy Powell earned two Oscar nods that year, for Goldmine and Shakespeare in Love. She took it for Shakespeare but years later declared, “I won it for the wrong one.” —LG
Everything about designer Tom Ford’s directorial debut is hauntingly beautiful: the cinematography, the interior design, and the early-’60s costuming. Ford, who helmed Gucci for a decade, brought his eye for sensual luxury to the big screen with precision; star Julianne Moore donned era-specific details (a sheath dress here, a drop earring there) that feel contemporary, no matter the era. —SR
Paul Schrader’s erotic thriller stars Richard Gere as a male escort whose moves are as smooth as his lapels, every ensemble a sleek symphony of slate and sand and camel hair. The man behind those looks? A then-obscure Italian designer named Giorgio Armani, whose clean-lined, gorgeously louche fashions for the film became his American calling card — and an indelible piece of movie history. —LG
In Norman Jewison’s heist caper, Steve McQueen’s smooth criminal sports a series of impeccably tailored three-piece suits — a fit still embraced by fashionable types. Still, McQueen’s debonair vibe didn’t come naturally: “He worked for weeks until he mastered life in a suit,” costar Faye Dunaway has said. Practice made perfect. —LH
Michelangelo Antonioni’s vivid snapshot of Swinging London revolves around an icon of that hedonistic era: the hotshot fashion photographer. David Hemmings stars as Thomas, an (exhaustively researched) amalgam of various real-life figures — most notably David Bailey — but Blow-Up’s style pedigree doesn’t end there. In addition to an early appearance from Jane Birkin, Veruschka makes a brief but indelible cameo, writhing on the floor in a slinky, sparkly, shockingly slit dress while Thomas straddles her, breathlessly taking photos. Fittingly, Blow-Up marked the auteur’s first English-language feature; the film’s eroticism never would have flown in Catholic Italy. —MS
As socialite Tracy Lord, Katharine Hepburn is haughty, capricious, tender, and vulnerable, vacillating between her ex-husband, C.K. Dexter Haven (Cary Grant), and a society reporter, Mike Connor (Jimmy Stewart). But it’s Hepburn who wears the pants — literally. The actress, who frequently fought to depict her characters in trousers and closely collaborated with costume designers, brought her love of menswear to set once again for Philadelphia Story and met her perfect match in Adrian. “He and I had the same sense of ‘smell’ about what clothes should do and what they should say,” she once said of the renowned designer. Hepburn’s casual, tailored elegance helped define an iconic American style more practical and individualistic than its fussier European counterparts. As Tracy Lord would say: My, she was yar. —Maureen Lee Lenker
Wong Kar-wai’s swooning portrait of two neighbors (Tony Leung and Maggie Cheung) in 1960s Hong Kong bonded by their spouses’ mutual infidelity comes dressed in the most exquisitely
period-perfect costumes: a parade of tailored suiting and patterned cheongsams so dreamy, it’s still hard to believe they could even exist on the same planet that contains sweatpants. —LG
Jenny (Ali MacGraw) first endears herself to Oliver (Ryan O’Neal) by calling him “preppy,” and it’s precisely that tweedy East Coast vibe that this film helped popularize. “On the heels of the psychedelic revolution, it brought preppy, classic style back,” film and fashion historian Kimberly Truhler says of the tearjerker. MacGraw came from the fashion world — she was a former assistant to legendary Harper’s Bazaar editor Diana Vreeland — and brought much of her own taste to the set. With Jenny’s camel coat, striped scarf, and a knitted beanie from the actress’ personal collection that instantly became the fashion must-have of the moment, MacGraw helped define 1970s trends and spurred legions of women to copy her boho-meets preppy look. Because love (and enduring style) means never having to say you’re sorry. —MLL
When Ruth E. Carter joined the Marvel Cinematic Universe with Black Panther, she didn’t just design costumes — she designed an entire nation. Wakanda is rooted in ancient African traditions and sleek technology, and Carter won an Oscar for her innovative, Afrofuturist vision of T’Challa’s homeland. From the Dora Milaje’s warrior armor to the royal family’s ceremonial garb, every look is, well, heroic. —Devan Coggan
Say what you will about Woody Allen (no, really), but nothing can take away the genius of the borrowed-from-the boys fashions in Annie Hall. With barely more than suiting and a well-placed hat, the wardrobe (by Ruth Morley, who also devised the looks for Taxi Driver and Kramer vs. Kramer) adds whimsy to the film’s neurotic tableau. The movie is at its aesthetic peak whenever Diane Keaton (the eponymous Annie) is on screen, and her much copied, menswear-influenced ensembles — which Keaton herself embraced before lending it to the character — is that rarity: a look that never goes out of style.
While Annie is the rom-com’s greatest sartorial strength, there are other moments worth mentioning: a paisley-esque caftan worn by Janet Margolin and paired with a larger-than-life beaded necklace and wire-frame glasses, a white-after-Labor Day look by Allen’s character, Alvy, and some tennis outfits that offer such an uplifting dose of Americana that they inspire something close to patriotism. La dee da indeed. —SR
A list of fashionable movies without Amy Heckerling’s influential teen comedy? As if! It’s been 25 years since Alicia Silverstone’s Cher Horowitz welcomed us into her candy-colored automated closet, teaching us that yellow plaid is the best way to make a statement and Alaïa is, like, a totally important designer. Costumer Mona May took inspirations from both light ’90s grunge (so much plaid!) and high-fashion European streetwear. Runway designers like Versace, Chanel, and Calvin Klein have used Clueless as inspiration ever since. “That was the most fun part, creating that unique look,” May says. “[We wanted] something that’s from the runways, mixed with the malls and then mixed with the thrift store.”
Silverstone had about 60 different costume changes throughout the film, each one more memorable than the last. May chose to eschew neutrals in favor of bright, youthful colors — again, that yellow! — and classic silhouettes like peacoats and shift dresses mean that Cher’s wardrobe still feels fresh a quarter-century later. “I think maybe part of the timelessness of the movie is because the fashion is still cool now,” May says. “Kids are loving it because it’s still wearable.” —DC
The breathtaking images in Berry Gordy’s romantic drama are in part thanks to star Diana Ross, who designed the film’s costumes. As aspiring fashion designer Tracy, she twirls in a striking rainbow outfit. But it’s the dreamy montage where she transforms into supermodel Mahogany that cemented Ross as the prototype for modern black Hollywood glamour. —MJ
Any mention of Grace Kelly tends to evoke a single phrase: classic beauty. God may have gifted her those impossible cheekbones, but it was Oscar-winning costumer Helen Rose who crafted the exquisitely elegant looks for what would be the star’s last screen role (Rose also designed the wedding dress Kelly wore to marry Prince Rainier III of Monaco that same year). Every drape and swirl of Kelly’s wardrobe in this breezy romantic farce is impeccable. From the blue organza cloud of a party gown to a pristine white swimming costume, she’s clearly already a princess — everything but the crown. —LG
The great miracle of Sofia Coppola’s lavish period piece is that it feels utterly immediate, not lecturing on the history of the doomed French queen so much as living inside it. Oscar winner Milena Canonero created star Kirsten Dunst’s wardrobe of sugary pink and airy blue gowns to reflect the perspective of the wearer — just a girl with an unchecked budget — and Marie’s timeless, teenage-dreamy point of view (along with a few cheeky anachronistic details) renders her 18th-century chic eternally, essentially modern.
Despite having been dead for a few hundred years now, Marie Antoinette remains one of the most enduring style icons in human history — just this February at Milan fashion week, Moschino unveiled an Instagram-friendly collection best described as Versailles à la anime — and Coppola’s film feeds that insatiable fascination with a fresh, girlish vision of the tragic monarch. And not only with the impeccable costumes: Gorgeous and indulgent across the board, including in its opulent settings (filmed on location at the famed château) and impossibly cool, new wave-heavy soundtrack, the film goes beyond being merely stylish — it’s a pure fashion fantasy.
But there’s a darkness, too, woven into Marie’s dainty pastels. The decadence on display is as damning as it is intoxicating, and that tension makes the biopic a testament to the seductive power of truly killer style. It’s enough to make a girl lose her head. —MS
Wes Anderson’s dramedy is an ode to faded glamour, and costumer Karen Patch gave every Tenenbaum a signature ’70s-inspired look, from Ben Stiller’s fire-engine-red tracksuits to Luke Wilson’s sweatbands. But it’s Gwyneth Paltrow’s chain-smoking, eyeliner-wearing Margot who endures as a fashion icon, rocking a fur coat, blunt bob, and general sense of malaise like no other. —DC
Breakfast at Tiffany’s is the obvious choice: As Holly Golightly, Audrey Hepburn’s LBD, strands of pearls, and oversize sunnies are nothing short of iconic. But for pure sartorial exuberance, consider the Tiffany’s predecessor Funny Face: Hepburn stars as a waifish bookseller turned fashion plate, donning couture gowns and sporty crop tops with equal aplomb. The film melds Hollywood and the fashion industry in much the same way Hepburn herself did. As Hubert de Givenchy, the famed Parisian designer who worked closely with her on Funny Face, Tiffany’s, and more, once said, “Audrey wore clothes with such talent and flair that she created a style, which in turn had a major impact on fashion.” Hepburn may have learned everything from the movies, as she famously quipped, but we learned everything about effortless elegance from her. —MLL
Neither the years nor the copycats can diminish the thrilling originality of Jean-Luc Godard’s seminal debut feature, which heralded a new era in filmmaking and has since become emblematic of the French New Wave. Endlessly surprising in its form, wit, and rhythm, the sexy crime drama pays an affectionate homage to Hollywood genre films and marks a high point of both cinematic and sartorial style — the perfect marriage of French chic and American cool.
Jean Seberg and Jean-Paul Belmondo are Patricia and Michel, the gamine and the criminal, both simultaneously artless and deliberate. Pixie-haired American-in-Paris Patricia styles herself à la française with cigarette pants, crisp striped dresses, and constant vocabulary questions for her dashing French boyfriend, Michel, who self-consciously emulates Humphrey Bogart and enhances his image with a steady stream of stolen American cars and a steadier stream of half-smoked cigarettes. Each of them is the other’s greatest accessory (along with Michel’s jaunty hat, which passes effortlessly between them), and six decades later, the striking pair proves that truly great style doesn’t fade over time — or get lost in translation. —MS