The 25 Most Fashionable Films of All Time

this article originally appeared in Vanity Fair. Most of these titles (with the exception of a couple) are available for rent on DVD at our store.

AMERICAN GIGOLO (1980) – There isn’t just one suit or jacket that stands out in American Gigolo. It’s the entire wardrobe worn by then newcomer Richard Gere, in the role of male escort Julian Kay, that leaves its mark. With eyes as narrowed and shaded as the venetian blinds that shutter his rooms, Gere moves through the demimonde of Los Angeles looking like a Roman prince and clothed by an Italian designer who was also new to most Americans, Giorgio Armani. Two stars were born: Gere, who looked like the King of Cats in Armani’s luxe yet languorous tailoring; and Armani, who put the purr in power dressing just in time for a new era of excess—the 80s of booms and bonfires.
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ANNIE HALL (1977) – Was it the black felt hat, like something a Shaker would wear? Or the black wool Civil War vest, with only the top button buttoned? Or the white oxford completed with a man’s silk tie? Or the khaki pants, so baggy they ballooned out at the hips? Whatever it was, it worked. This kookily curated outfit gave birth to the Annie Hall look—part Charlie Chaplin, part Granny’s attic. Not since Love Story, in 1970, when Ali MacGraw pulled a knitted cloche down over her eyebrows, had a female movie character so effortlessly sent a wave through fashion. Woody Allen’s Annie Hall was the first of his films in which he invested a piece of his heart. Diane Keaton, who played the title role, had been Allen’s real-life lover and muse. When the costume designer objected to Keaton’s using her own clothes in the film, Allen said, “Leave her. She’s a genius.” His trust in Keaton’s choices—a layering that was actually liberating, a magpie appropriation of men’s wear that accentuated the girl in her—came through. Women liked what they saw: a free spirit finding her way. But more than that, they liked what they felt: his admiration for her.
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ANOTHER COUNTRY (1984) – Oh, the ineffable, elegiac style of the En­glish public school! Rumpled cricket whites and striped silk ties, cutaway coats and starched collars, stretched-out jumpers and moth-eaten tweeds. In Another Country, set in the 1930s and filmed around Oxford University and Althorp, the family seat of the Earl of Spencer, the sartorial splendor of boys being groomed to the ruling class is an idyllic vision (not to mention a Ralph Lauren dream) of young manhood. It is also a way to contain and tailor the boys to principles and prejudices that will both armor and diminish them. The school is the crucible, a place of high pressure, and the beauteous Rupert Everett plays the homosexual Guy Bennett—loosely based on the infamous double agent Guy Burgess—who won’t be contained.
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THE AWFUL TRUTH (1937) – Of all the comic actresses in the grand march of movies, Irene Dunne is in a class by herself. Perhaps it’s because she trained in opera. Her tonal range, her handling of timbre and timing, her light touch and quick glances into emotion, are virtuosic. She’s the bubble in the champagne—a mezzo-soprano bubble—and she was never bubblier than in The Awful Truth, the most breezily LOL-funny entry in the screwball genre. In this film everything slides into spontaneous synchronicity: Dunne, Cary Grant, the terrier Mr. Smith, the wedding-cake whites of upper-class living rooms, and the Kalloch gowns Dunne wears with such élan. When she enters her first scene in a ridiculously pouffy white fox fur—she’s an eiderdown bed, a Baked Alaska—we know we’re in for a treat.
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BELLE DE JOUR (1967) – Long a point of reference for the fashionistas at the glossy magazines, Luis Buñuel’s Belle de Jour offers up the blanc-de-Chine beauty of Catherine Deneuve, who plays the upper-class Séverine Serizy in one nifty little Yves Saint Laurent day dress after another. These exquisitely simple shifts and double-breasted A-line coats, hemmed innocently to the knee, belie the baroque sexual fantasies of Deneuve’s character—from whipped slave to bound Saint Sebastian to precocious schoolgirl. With her tumble of hair pulled back into tight buns and gleaming French rolls, she suggests an over-the-top Hitchcock blonde—the heroines of Vertigo, The Birds, and Marnie absorbed into one damaged, deceptive persona.
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THE BEST OF EVERYTHING (1959) – The Best of Everything can’t boast a couture aesthetic or a continuous parade of mouthwatering fashions. Rona Jaffe, the author of the best-selling 1958 novel on which the movie is based, stressed to director Jean Negulesco that she wanted it “real, real, real.” This meant modest little dressmaker suits and shirtwaists, those 1950s Paris knockoffs that were made in affordable blends and sold at Saks and Macy’s. One of the charms of the movie is that its ambitious young women, with their strands of pearls, their scarves and hats and gloves, capture so well the studied loveliness that is now so far away. Re-creating the publishing offices of Pocket Books and the midcentury chic of small Manhattan apartments, The Best of Everything succeeds in getting it right. Suzy Parker, at the time the most successful model in America, was cast as the aspiring actress Gregg Adams. Wearing a red satin gown with a wide décolletage, flush with the triumph of getting her first big laugh in a new play, she flashes her ravishing Suzy smile, and the glamour is real, real, real.
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BLOW-UP (1966) – It’s not a whodunit; it’s a what-happened. Michelangelo Antonioni’s Blow-Up has been called a time capsule of Swinging London, and it’s got the Space Age shifts and mod makeup (iconic), casual sex and pot parties (controversial), leggy Jane Birkin of Hermès “Birkin bag” fame, and even leggier Veruschka—in one of the most erotic fashion shoots ever filmed. At the center of it all, David Hemmings, playing a David Bailey–like lensman in skinny white Jagger-esque jeans, is kinetically fascinating. With his Rossetti profile and burning blue eyes, he’s like a surly archangel or Mallarmé’s faun (“Did I love a dream?”)—unsure of what he’s seen. You could say the movie is about the culture of seeing versus the nature of seeing. And that’s what fashion is all about.
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BONNIE AND CLYDE (1967) – Bosley Crowther, film critic of The New York Times, left (some say lost) his job not long after relentlessly attacking Arthur Penn’s Bonnie and Clyde. He thought it was camp, farcical, and brutal, but he proved out of step with the era, for audiences “got” the movie and The New Yorker leapt to its defense, lauding its tonal complexity, the way comedy morphs into drama, and the bloody torrent of bullets at the end. Such overkill is no longer shocking, but in 1967 it was stunning, silencing. That Faye Dunaway and Warren Beatty wore Theadora Van Runkle’s Depression-era duds with such glamour (in her beige beret, Dunaway looks like a cover girl) only added to the sense of a stylistic currency newly minted.
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BREAKFAST AT TIFFANY’S (1961) – When it comes to Audrey Hepburn as style icon, Break­fast at Tiffany’s is ground zero. This movie has pedigree, beginning with Truman Capote, the man who wrote the novella it’s based on and who would swim with the swans of the best-dressed list—Babe Paley, Gloria Guinness, C. Z. Guest (that is, until he dissed them all with “La Côte Basque, 1965”). Dorian Leigh, one of the great models of the 40s and 50s, was one of the inspirations for Capote’s heroine Holly Golightly. Add Hubert de Givenchy’s designs for Hepburn, Pauline Trigère’s for Patricia Neal, and the best too-crowded cocktail party ever filmed, and you have off-the-charts sophistication. That the movie also captures the melancholy of Manhattan only deepens its effects. The opening sequence is profound: Hepburn, wearing that inexpressibly elegant black satin sheath (one sold for $923,187 at Christie’s in 2006), emerges from a cab at dawn, walks toward Tiffany & Co., and pulls coffee and a pastry from a paper bag as she stares into one of the windows. Where has she been all night? Why is she here? Her reflection in the glass turns her into one of Tiffany’s baubles, something that can be bought. Thus the story begins.
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FLASHDANCE (1983) – Flash dancing dates to the 1920s and 30s, when the great African-American jazz tap acts—the Nicholas Brothers, the Berry Brothers, the Four Step Brothers—ramped up the technical difficulty by adding acrobatics to their routines. These dances were showstoppers. In fact, you can draw a line from 30s flash dance to the extreme splits and spinning of 70s hip-hop and break dancing. Flashdance took the flash and gave it to a female, and not just any female, but gorgeous Jennifer Beals, whose father happened to be African-American, which made for a pleasing historical symmetry. The movie was the first collaboration of Don Simpson and Jerry Bruckheimer, and critics hated it. But audiences loved the story of Alex, an 18-year-old welder by day and exotic dancer by night. They loved the sexy, super-aerobic flash dances (which were basically MTV videos built into the movie) and loved the way Beals seemed always to be half in and half out of her clothes, as if in a continuing state of metamorphosis. Men’s undershirts and oversize jackets. Knit leg warmers bunching like caterpillars. Most iconic of all is the loose, torn sweatshirt Alex lives in—the fabric cocoon from which she is emerging.
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FUNNY FACE (1957) – They can’t make movies like this anymore. Its wit, mesh of talents old and new, roots in the stage, love of the beautiful, ear for fashion-speak, way with a song, seriousness about silliness, and all-around perfect pitch blossomed forth from a culture of apprenticeship and experience in which computer screens, apps, and instant answers didn’t exist. Stanley Donen’s Funny Face is a confection, an enchanting spoof. It makes a musical of the real-life collaboration between fashion phenomenon Suzy Parker, a beauty with brimming energy who cared more for ideas and art than for café society, and wunderkind Richard Avedon, who in his Paris reports for Harper’s Bazaar used Parker’s energies to bring action to fashion photography, transforming the “sitting” into a “shoot.” Young Audrey Hepburn is Parker, Fred Astaire is Avedon, and the incomparable chanteuse (and Eloise author) Kay Thompson is the salty Diana Vreeland–ish editor of a fashion magazine called Quality. Throw in a dash of Sartre, some bongos, the fashions of Givenchy, location shooting in Paris, and a pas de deux in white tulle to George and Ira Gershwin’s “He Loves and She Loves,” and, well, we love.
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THE GODFATHER (1972) – ‘Where’s Michael?” asks Don Vito Corleone (Marlon Brando) during the wedding scene near the beginning of The Godfather. “We’re not taking the picture without Michael.” The don’s youngest son, played by Al Pacino, is the child kept clean of the family business (La Cosa Nostra), the one who will assimilate within the law. When we first see him he’s in uniform, having returned from World War II a hero. Imperceptibly he’s drawn back into the bosom of the family. “You don’t catch him acting,” wrote Pauline Kael, in 1972, “yet he manages to change from a small, fresh-faced, darkly handsome college boy into an underworld lord.” Costume designer Anna Hill Johnstone helped work the change, moving Michael from irresolute shades of brown to darker, deeper blacks. During a year in hiding, in Sicily, he goes native, wearing linen and rough wool. Michael returns to America with an ancient gravity, an Old World sense of sight. He doesn’t wear a fedora or derby, as Cagney and Bogart did; he wears a Homburg, the brim of which he often pulls down, peasant-like. Gangsters almost always look good—they’re the dandies of darkness—but not until Michael Corleone, in the lustrous plies of his black wool suits, did we see the Lucifer of Paradise Lost, who before his fall was the most beautiful angel of all.
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THE GREAT GATSBY (1974) – Summer whites, cable knits, beaded sheaths, and crisp oxfords set against green lawns and blue skies full of sea. Theoni V. Aldredge won an Oscar for her costuming of The Great Gatsby, and Ralph Lauren won acclaim for the suits he fashioned for the male leads, most notably the pink suit Jay Gatsby (Robert Redford) wears on the novel’s fateful day. Academics have analyzed the way color plays a role in F. Scott Fitzgerald’s masterpiece of mon­ey, dreams, and fatal naïveté, and the symbolism of Gatsby’s pink suit is often invoked, if never quite explained. It offends the hostile husband of Daisy Buchanan (the woman Gatsby loves), but as one of the most singular suits in movies, it mesmerizes the rest of us. Very pale, completely surprising, it suggests a childlike trust, the strange purity that will undo this strange man.
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A HANDFUL OF DUST (1988) – A Handful of Dust was released just seven years after Granada Television’s magnificent 11-part Brideshead Revisited was first aired. Both came from novels by Evelyn Waugh, both are set between the wars and revolve around a great English estate, and both were costumed by Jane Robinson. The En­glish­man in his tweeds, in hunting pinks and balmacaans, exudes a pastoral privilege like no other on earth. The Englishwoman, however, no matter how highborn or beautiful, can tend toward the dowdy (read Nancy Mitford!). Not so Kristin Scott Thomas here. As Brenda Last, when she appears in a snow-white twinset, dipping her spoon into a snow-white pudding, she’s like meringue—though the fox furs she later wears hint at the vixen in her. Sliding into adultery, she gleams in one mouthwatering satin gown after another. Alas, the little fox outsmarts herself and is gobbled up by fate.
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LA DOLCE VITA (1960) – Federico Fellini’s La Dolce Vita may be the only cinematic masterpiece born of a dress. Strange but true: it was Cristóbal Balenciaga’s sack dress of ’57 that inspired Fellini’s vision. As his co-screenwriter, Brunello Rondi, has said, “These sack dresses struck Fellini because they rendered a woman very gorgeous who could, instead, be a skeleton of squalor and solitude inside.” Interestingly, there are no sack dresses in the movie. La Dolce Vita’s most memorable fashion moment comes when Anita Ekberg, spectacular in a white mink stole over a revealing strapless black gown, her creamy breasts bobbling, completes her ensemble by balancing a tiny white kitten on her head. It is crying for milk. Analyze that!
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LAST YEAR AT MARIENBAD (1961) – Where would modern fashion photography be without Alain Resnais’s mysterious Last Year at Marienbad? And what about the postmodern theater of Pina Bausch and Robert Wilson, both choreographic masters of slow motion, repetition, and the non sequitur. Last Year is like a black-and-white fashion fantasy in which the models in still photos come to life and question existence. It’s a Twilight Zone that sees store mannequins in evening clothes drifting through gilded rooms and formal gardens, trying to pin down reality. A white feather dress suggests Schiaparelli gone mad. This alternate universe with its ghostly chic was pivotal. But no one can quite say why.
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MOROCCO (1930) – Released by Paramount three years into the talkie era, Morocco is still under the spell of silence. Mihrabs, grilles, and minarets, billowing veils and latticed back alleys—all whisper of otherworldly ways. The film’s pale silvers and misted grays are evocative of an Orientalist postcard, the erotic artifact of a forbidden desire (a bare-breasted woman is visible in an early scene). Directed by Josef von Sternberg, Morocco was Marlene Dietrich’s first American film and the first time she would be seen on the big screen wearing a man’s white tie, tails, and top hat. The flowing and asymmetrical dresses she later wears are like puzzles in which her enigma is wrapped. But it’s Dietrich in that tux—her stiff-fronted white shirt, like a bib, setting off the baby-soft face she has yet to grow into—that is fixed in the eye forever.
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NORTH BY NORTHWEST (1959) – The “suits,” they’re called, those faceless men who are big wheels in the corporate machine. Or the “man in the gray flannel suit”—that commuting member of the postwar boom, his existential questions buttoned down like his shirt collar. But has ever a gray suit gone through more—chased, crop-dusted, run over, shot at—than the one worn by the Madison Avenue advertising executive Roger O. Thornhill in Alfred Hitchcock’s thriller of mistaken identity, North by Northwest? More to the point, has a gray suit ever been more elegantly yet athletically inhabited? Cary Grant, who plays Thornhill, was an acrobat in his youth, and the handsprings remained in his muscles—he often looked a little caged in his clothes. But here one thinks of Anne Hollander’s description, in her book Sex and Suits: The Evolution of Modern Dress, of the modern suit: “an exquisitely balanced garment that fitted smoothly without wrinkles and buttoned without strain, to clothe what appeared to be the torso of a Greek athlete.” A distinctive shade of slate, Grant’s suit was made by Norton & Sons of London.
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THE PHILADELPHIA STORY (1940) – Adrian, the prolific costume designer at MGM during its greatest decade, the 30s, was not long for the studio when he costumed The Philadelphia Story. He’d reached the heights of fantasy with Marie Antoinette in 1938 and The Wizard of Oz in 1939. Over the top is where he liked to go, and he’d get to go there only one more time, with Ziegfeld Girl, in 1941. The Philadelphia Story, sandwiched in between, had to be more believable. Still, it’s as if Adrian took to heart a comment from the character Macaulay, played by James Stewart: “The prettiest sight in this fine, pretty world is the privileged class enjoying its priv­i­leges.” None are more privileged than Tracy Lord, the willful heiress played by Katharine Hepburn, of the patrician jaw and lean Wasp lines. Throughout the movie she is compared to a “queen,” a “goddess,” a “statue.” These are not compliments. Adrian accentuates her Olympian cool in clothes with Hellenic motifs. Even her bathrobe is draped à la grecque. When she softens, her floating wedding dress of transparent silk organza makes for one of the finest—and indeed prettiest—transformations in movies.
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REAR WINDOW (1954) – The rear window in Alfred Hitchcock’s thriller of the same name looks out on a Greenwich Village courtyard banked by rows of other rear windows, most of them open (it’s 1954, A.C. was rare). The boxy spaces inside the rectangular windows begin to make one think of dioramas, terrariums, stage sets. Inside each is a different species of love or absence of it. Laid up with a broken leg, photojournalist L. B. “Jeff” Jefferies (James Stewart) keeps tabs on the human zoo from his window. Meanwhile, his “too perfect” girlfriend, the fashion editor Lisa Fremont (Grace Kelly)—she’s the hothouse flower in this asphalt jungle—is angling for a commitment. She visits night after night wearing Edith Head’s most brilliant ensembles, an unforgettable catwalk of characterization. A full skirt of white silk organza turns her into “a snow-covered volcano”—Hitchcock’s description of her. The eau de Nil green suit suggests the moneyed power of the society girl (Hitchcock would put Tippi Hedren in the same green in The Birds). And a girlish flowered shirtwaist allows Lisa to leap Diana-like into action, dazzling Jefferies. Posing, lounging, pacing, Kelly fills the space and the screen with cultured femininity. When strange doings are viewed through a window across the courtyard, Jeff’s and Lisa’s cross-purposes are united in a shared purpose: solve the mystery! An haute tutorial on the seductions of seeing, Rear Window is as perfectly conceived, constructed, and accessorized as Lisa Fremont herself.
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REBEL WITHOUT A CAUSE (1955) – Teenagers were a growing dem­o­graphic power in the 1950s, and the red windbreaker worn by James Dean in Rebel Without a Cause sends the message. There are various theories on the jacket’s origin: that costume designer Moss Mabry made it; that director Nicholas Ray got it from a Red Cross worker; that it was bought in a department store. There’s no question that the color was a conscious decision. Red—for life, blood, defiance, daring—unites the characters of Dean, Natalie Wood (her bright-red coat), and Sal Mineo (his one red sock). Each is trying to survive high school and transcend disillusionment. One of them doesn’t make it, and is zipped into the windbreaker in a final symbolic note.
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SABRINA (1954) – Forget the Disney lineup of mermaids, Snow Whites, and Rapunzels. For a certain breed of young woman, Billy Wilder’s Sabrina is the fairy tale that changes everything, the Cinderella standard from which it’s hard to recover. (“Sabrina ruined my life,” said one of the most sophisticated women I ever knew, over scotch.) It’s Glen Cove, Long Island, in the 50s, a land of lightning bugs and martinis, pearl chokers and plenty. It’s life as only happens in the movies, where the brothers to choose between are William Holden and Humphrey Bogart. And it’s Audrey Hepburn as the chauffeur’s daughter, straight off her success in Roman Holiday and in glorious first bloom. Her dancer’s body and sylvan grace make her an ideal mannequin, and the clothes she wears after her Paris transformation—designed by Hubert de Givenchy, with some interpolations by Edith Head—are to die for. Try to pick a favorite: the slim suit, the swan gown, the boatneck dress with bows on the shoulders. It’s impossible. Even in black Capri pants, she’s sublime.
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THE THOMAS CROWN AFFAIR (1968) – ‘I’ve got all the numbers,” says Steve McQueen as the title character in The Thomas Crown Affair. A multi-millionaire investment banker who wears Gatsby-esque three-piece suits and has a to-do list that’s timed to the minute, he is a precision instrument in need of thrills, and when he robs a bank for the fun of it he gets his biggest thrill yet—the divine Faye Dunaway as an insurance investigator in hot pursuit. Thea Van Runkle was responsible for Dunaway’s covetable wardrobe of stylish miniskirted suits, all buttoned up and belted. The movie as a whole, produced and directed by Norman Jewison, is deeply stylish, with a buttoned-up eros all its own.
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WALL STREET (1987) – It’s the suspenders. We’d seen the snazzy pin-striped suits before. We’d seen the slicked-back hair. But when men’s custom-clothing guru Alan Flusser added vertically striped shirts and those crowing, cock-of-the-walk suspenders—in stripes, in polka dots—to Michael Douglas’s wardrobe for Wall Street, he created a new archetype of amorality. What is it about Gordon Gekko’s suspenders? Perhaps it’s the way they suggest the high-wire act of high finance, the soul suspended over the pit.
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WITHNAIL AND I (1987) – Bruce Robinson’s Withnail and I is set toward the end of the Swinging London 60s and follows two out-of-work and somewhat demoralized actors on a benighted trip to the country. Who knew this grungy little movie would end up a cult film? Or that the Harris tweed “Withnail Coat” would become a global object of desire? It is worn by Richard E. Grant and is actually based on a 19th-century riding coat—which has a rakish military fit across the chest and then flares long, with high vents that make the coat dance. It was designed by Andrea Galer, who said she wanted the coat to look as though it had come from the family attic. Lineage, history, the spine of England! Withnail in his princely coat goes all the way back to Shakespeare.
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Read the whole article HERE.

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