Fashion on film: The 20 most stylish films to watch for escapism

From spellbinding aesthetics to scene-stealing costumes, here's what to watch when you're in need of some sartorial inspiration

There are some films you watch for the spellbinding performances, others you watch for the whip-smart script or the superb cinematography. And then there are the films you watch simply for the sheer beauty of them – for the sumptuous aesthetics, the elegant custom-made wardrobes, the jaw-dropping glamour. In these times of turmoil and uncertainty we could all do with a bit of elevated escapism, whether that’s through Wes Anderson’s distinctly quirky vision, Diane Keaton’s sublime wardrobe in Annie Hall or a bit of Fellini magic via La Dolce Vita. Here we’ve rounded up the 20 most stylish films of all time, guaranteed to make for some seriously sartorially uplifting viewing.

The Talented Mr Ripley, 1999
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Anthony Minghella’s psychological thriller, a take on Patricia Highsmith’s novel, follows the unlikely friendship between playboy Dickie Greenleaf (Jude Law) and sociopath Tom Ripley (Matt Damon), alongside charming dilettante Marge (Gwyneth Paltrow). The setting is the glamorous 1950s Italian Riviera and, as you’d expect from Minghella, a longtime purveyor of stylish films, the aesthetic is molto bene. The audience is transported between pristine beaches and idyllic fishing villages, by way of a sumptuous apartment in Rome and the crumbling grandeur of Venice, for which costume designers Gary Jones and Ann Roth, who earned an Oscar nomination for their efforts, created a Mediterranean-chic wardrobe. While the boys channel East Coast preppy mixed with a rumpled elegance (casual suits, fine linens, vintage knitwear), Marge is a masterclass in summer style with her printed full skirts, crisp white knotted shirts, high-waisted bikinis and Alice bands.

Breathless, 1960
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There’s a scene in Jean-Luc Goddard’s 1960 crime drama – about a wandering criminal (Jean-Paul Belmondo) and his American girlfriend (Jean Seberg) – when the protagonists are walking down a street together in Paris. He’s in a loose-fitting jacket and trousers, accessorised by aviators and a cigarette, she’s channeling gamine chic in a striped Breton-esque top paired with a pleated skirt and a pixie cut. The whole vibe is effortlessly cool. Interestingly, there was no costume designer or official costumes for this movie. Rather, Godard encouraged his actors to choose what to wear, perhaps explaining why every outfit – skinny pants, trench coats, ballet pumps and simple summery frocks for her, shabby suits, fedoras and stubby ties for him – still feels so relevant. This film didn’t just herald the French New Wave of cinema, it was the epitome of French dash too. 

3 Women, 1977
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3 Women is one of director Roger Altman’s earliest works, and undoubtedly one of his greatest. The 1977 American avant-garde drama film – about the complex twists and turns of a relationship between three women (Shelley Duvall as Millie, Sissy Spacek as Pinky and Janice Rule as Willie) – is eerie and surreal, perhaps because the story came from a dream Altman had. It’s about “empty vessels in an empty landscape,” he once said, by way of explanation. While the plot gets evermore bizarre, against the backdrop of the California desert, one thing is for certain: the girls’ wardrobe is exceptional. Think prairie dresses, long flowing skirts and housecoats, in the softest pastel tones. The costume designer, Jules Melillo, gave each character a signature colour; Millie channels yellow, Willie wears earthy tones, and Pinky wears… you guessed it, pink.

Belle du Jour, 1967
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Catherine Deneuve stars as the titular role in Luis Bunuel’s 1967 Belle De Jour, about a bored housewife, Séverine Serizy, who counters her ennui by taking up afternoon work in a brothel. The film is credited as being one of the first to truly push boundaries in its depiction of female desire. The film is also a paragon of Parisian chic, with Séverine’s entire wardrobe created by Yves Saint Laurent; it was a perfect match, as the designer was busy transforming haute couture for a new era of youthful, strong, independent women. According to the Musée Yves Saint Laurent in Paris, “Séverine is at once fragile and seductive, especially in the legendary black vinyl trench coat with knit sleeves and the austere black dress with ivory satin cuffs and collar.” Other highlights include the safari dress with its gold belt, and a red A-line dress with matching Eisenhower jacket. So popular were YSL’s designs for the film, they found their way into popular fashion, with sales of the trench coat – part of the rive gauche 1966 collection – increasing due to the film’s popularity.

Annie Hall, 1977
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Woody Allen’s Oscar-winning romantic comedy, about the relationship between neurotic New York comedian Alvy Singer (Allen) and the ditsy Annie Hall (Diane Keaton), is famous for its kookiness and offbeat comic timing. But let’s not forget its 1970s sartorial flair. It is said that Annie’s androgynous dress sense was a reflection of Keaton’s own wardrobe – Allen is reported to have let the actress have a big say in what her character wore on screen (“She’s a genius! Let’s just leave her alone, let her wear what she wants,” he told costume designer Ruth Morley). So, it is Keaton we largely have to thank for the ties, shorts, waistcoats, supersize blazers and high-waisted, wide-leg trousers, all flawlessly layered and accessorised. 

Carol, 2015
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It is hardly surprising that costume designer Sandy Powell has 15 Academy Award nominations and three wins under her belt. From Shakespeare in Love and The Favourite to Gangs of New York and The Wolf of Wall Street, Powell can turn her hand to any epoch. For Carol – Todd Haynes’ adaptation of another Patricia Highsmith novel, which tells the story of forbidden love between aspiring photographer Therese Belivet (Rooney Mara) and Carol, a wealthy older woman going through a divorce (Cate Blanchett) – she and production designer Judy Becker brilliantly encapsulate the bygone glamour of 1950s New York. Powell consulted fashion magazines from the era to create Blanchett’s wardrobe from scratch (very little of it is vintage) with a series of fur coats, slim-fitting Hattie Carnagerie-style suits and dresses, rich fabrics and luxe accessories; Mara, by contrast, is more about layering, bold patterns and full skirts. Both looks are perfect.

The Millionairess, 1960
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With Sophie Loren playing the richest woman in the world alongside Peter Sellers in this 1960 romantic comedy, there could never be any doubt that the aesthetic would be lavish. Not least Loren’s wardrobe, which was designed by Pierre Balmain. The French fashion designer pulled out all the stops, sending the Italian actress onto the set in a series of show-stopping ensembles in lace, satin and sequins, accessorised with feather hats, fur shawls and strands of pearls. Standout, however, has to be Loren’s black belted leather dress, worn with a leather hat and leather purse. Paired with black heels and big sunglasses, it’s the ultimate in sass.

Bonnie and Clyde, 1967
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When Arthur Penn’s biographical film – about ruthless couple Bonnie Parker (Faye Dunaway) and Clyde Barrow (Warren Beatty), who went on a crime spree across America during the Great Depression – was released in 1967, it divided opinion. Criticised for gratuitous violence, the film was initially relegated to drive-ins and second-tier movie theatres. However, on re-release it soon became a cult classic, thanks in no small part to the captivating performances of its lead actors and their equally mesmerising looks. Beatty and Dunaway are the epitome of gangster chic, thanks to costume designer Theadora Van Runkle, who received an Oscar nomination for the film. Dunaway channels icy cool in her bias-cut midi skirts, knitted sweaters, silk neckerchiefs and jaunty beret. As Van Runkle once said: “The beret was the culmination of the silhouette. In it, she combined all the visual elements of elegance and chic. Without the beret, it would have been charming, but not the same.” Beatty is equally as dapper in his sharp pinstripe and herringbone suits and fedora.

A Bigger Splash, 2015
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Tilda Swinton plays a famous rock star, holidaying with her husband on the sun-drenched Italian island of Pantelleria; the unexpected arrival of an old friend (Ralph Fiennes) and his daughter (Dakota Johnson) heralds jealousy, passion and danger. The smouldering drama is loosely based around Jacques Deray’s psychological thriller La Piscine, and much of the action takes place at a dreamy Mediterranean villa, specifically its swimming pool. Cue a series of superlative summery outfits, specifically in Swinton’s case, whose film wardrobe was by Dior, either created for the film or from Raf Simons’ collections. Whether it’s a white silk jumpsuit, striped shirt dress or a floral silk kimono, all topped off by DiorFuturist sunglasses, this is a lesson in vacation dressing.

The Danish Girl, 2015
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A remarkable love story, loosely inspired by the lives of Danish artists Lili Elbe and Gerda Wegener and based on David Ebershoff’s novel of the same name. When portraitist Wegener (Alicia Vikander) asks her husband Einar (Eddie Redmayne) to stand in for a female model, it heralds Einar’s groundbreaking journey as a transgender pioneer, eventually renaming herself Lili Elbe. The drama – set in 1920s Copenhagen and then Paris – is not just brilliantly acted, it’s gorgeous to watch, with Art Nouveau-inspired sets by production designer Eve Stewart and exquisite costumes by Paco Delgado, in which he references Paul Poiret, Jeanne Lanvin and Coco Chanel. “When they moved to Paris and Lili was freer to be herself, we tried to use much more avant garde fashion of the period and we used a warmer palette and different fabrics like silks and chiffons just to show movement and a much freer spirit,” Delgado has said.

In the Mood for Love, 2000
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Wong Kar-Wei’s classic has been described as “a masterful evocation of romantic longing and fleeting moments”. The love story – based in 1962 Hong Kong – follows the story of Chow Mo-wan (played by Tony Leung) and Su Li-zhen (Maggie Cheung), who move into the same apartment block and gradually come to the realisation that their spouses are having an affair. Through the shared heartbreak, they too grow feelings for each other, though this love is unfulfilled. It’s sensual, seductive and seriously desolating all at once, enhanced by the extraordinary cinematography, score and, of course, the production and costume design. A highlight has to be the series of elegant, close-fitting cheongsams worn by Cheung; not least in the film’s iconic scene when Chow Mo-wan and Su Li-zhen decide to part ways after a rainstorm. Surely one of the most heartbreakingly beautiful moments in cinema history.

La Dolce Vita, 1960
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Federico Fellini’s masterpiece – which premiered 60 years ago – follows a week in the life of suave gossip journalist Marcello Rubini (Marcello Mastioanni) as he leaves provincial life behind to soak up the sophistication and decadence of Rome. As he navigates the modern hedonism of the city, in his sharp suits, slim ties and jet-black sunglasses (worn indoors and at night), he becomes increasingly disillusioned with the paparazzi lifestyle (this is where the word ‘paparazzi’ was coined) and the morally questionable high society he was reporting on. It’s satire at its very best and won the Palme d’Or at the 1960 Cannes Film Festival. It is also a byword in Italian style and elegance thanks, in large part, to Piero Gheradi, the film’s set and costume designer who won an Oscar for his efforts.

Breakfast at Tiffany's, 1961
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Any most-stylish-film list would be incomplete without the Oscar-winning Breakfast at Tiffany’s, about an unfolding romance between Holly Golightly (Audrey Hepburn) and aspiring writer Paul Varjak (George Peppard), based in 1960s New York. Indeed, there can be no more iconic scene than when Golightly, sipping coffee and nibbling a Danish, eyes hidden by huge sunglasses, jumps out of a cab early-morning wearing a black sleeveless satin evening gown, adorned with a dazzling pearl necklace, tiara and black elbow-length gloves, to peer at the display window at Tiffany, New York. It’s a look immortalised for generations, thanks in large part to its creator Hubert de Givenchy – a close friend of Hepburn’s – and legendary costume designer Edith Head. The film also cemented the ‘little black dress’ as a timeless classic. “I should be a stylish Holly Golightly. Even if that’s all I can contribute”, Hepburn once said. That, she certainly did.

A Single Man, 2009
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When Tom Ford announced he would be directing an adaptation of Christopher Isherwood’s novel A Single Man, set in 1960s Los Angeles about a day in the life of the unhappy, single George Falconer (Colin Firth), there was never any doubt it would be aesthetically impeccable. This is, after all, the man who mega-successfully helmed womenswear and menswear at Gucci, Yves Saint Laurent and his own eponymous line. But a collaboration with costume designer Arianne Phillips on the project (whose credits include the Johnny Cash biopic Walk the Line, as well as designing Madonna’s concert costumes) sealed his directorial debut as visually unforgettable. The vintage wardrobe worn by Firth and his co-star Julianne Moore is nigh on perfection; immaculate suits, crisp white shirts, well-polished black leather Oxfords and thick-framed glasses for him, and that long black-and-white dress for her (which, interestingly, was procured on eBay).

High Society, 1956
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If ever there was a fashion icon, it is Grace Kelly. The actress – who gave up the silver screen at the age of 26 to marry Prince Rainier of Monaco – was the definition of elegant 1950s minimalism in her twinset and pearls, sweetheart necklines, nipped in waists and sweeping satin gowns. “I favour pearls on screen and in real life,” she once said. Such was her cachet, she was the muse behind Hermès’s Kelly Bag. The films she starred in were equally as stylish, most notably High Society, for which costume designer Helen Rose ensured Kelly’s film wardrobe was impeccable, from the tulle skirts to the snappy shirt dresses and capri pants. But it’s the dusky pink, silk organza bridal dress, with its embroidered flowers, that is the scene stealer. Only to be eclipsed three months after the film’s release, when Kelly married into the Monegasque royal family wearing a wedding gown (also designed by Rose) that took 30 seamstresses six weeks to make, a fairytale vision in vintage lace and peau de soie.

Paris, Texas, 1984
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The ultimate road movie, directed by Wim Wenders and written by Pulitzer Prize-winning playwright Sam Shepard, about a near mute drifter Travis (played by Harry Dean Stanton) who tries to reconnect with his young son, his brother (Dean Stockwell), and his former wife Jane (Natassja Kinski). A story of personal identity it may be, but it’s hard not to get distracted by the stunning performances, Ry Cooder’s score and, of course, the sweeping cinematography which showcases the Texan desert in all its glory. And though Wenders once said, “The world of fashion. I’m interested in the world, not in fashion! But maybe I was too quick to put down fashion. Why not look at it without prejudice?”, the film has some iconic style moments, too. Not least the shocking pink fluffy sweater Jane is wearing when Travis tracks her down at a strip club.

Phantom Thread, 2017
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As you’d expect from a film set around the world of 1950s haute couture and loosely based on the life of Spanish designer Cristóbal Balenciaga, Paul Thomas Anderson’s Phantom Thread is stylistically flawless. Daniel Day-Lewis plays Reynolds Woodcock, a renowned dressmaker who, alongside his sister (Lesley Manville), dresses the haut monde of London. When he meets the fiery Alma (Vicky Krieps), who becomes his muse and lover, Woodcock’s fastidious, perfectionist life slowly starts to unravel. Famous for his method acting, Day-Lewis prepared for the role by studying fashion under Marc Happel, the New York City Ballet’s costume director – indeed, he even recreated a Balenciaga dress on his own from scratch. It’s no surprise the actor had a significant input into how Woodcock himself would dress – all softly tailored suits, tweed jackets and a bespoke raglan sleeve herringbone overcoat. Much of the film takes place in a Georgian townhouse masquerading as a fashion studio of the era, where a stream of wealthy women try on exquisite pieces, in rich silks, velvets and lace, created by award-winning costume designer Mark Bridges, real couture seamstresses and a “cutter,” Cecile Van Dyke.

The Royal Tenenbaums, 2001
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This comi-drama about the highly eccentric and dysfunctional Tenenbaum family – Royal (Gene Hackman), his wife Etheline (Anjelica Huston) and their three children Chas (Ben Stiller), Margot (Gwyneth Paltrow), and Richie (Luke Wilson) – has Wes Anderson written all over it… the distinctive narrative style, dark humour and the quirky creative. As befits the auteur, costume designer Karen Patch was told “Don’t shop – make everything!” The result is vintage sublimity with an emphasis on retro sportswear – Richie’s camel suit, Borg-esque headband and huge Vuarnet sunglasses combo is iconic. Though it’s undoubtedly the chain-smoking, heavy-on-the-eyeliner Margot who takes the limelight in her fur coat, striped Lacoste tennis dresses, Bass loafers and Hermès Birkin.

Rear Window, 1954
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Any film with Edith Head on its credits is always going to be a visual tour de force. The costume designer worked with Alfred Hitchcock on all his Paramount films including this one, a 1954 American Technicolor thriller. Starring James Stewart and Grace Kelly, it tells the story of famous photographer L.B. Jeffries (Stewart), who is confined to a wheelchair with a broken leg. Bored, he spends hours spying on neighbours from his apartment window, becoming convinced that one of them has committed murder. Kelly plays his fiancée, Lisa Carol Fremont, a stylish socialite with a striking wardrobe. As Hitchcock wrote in his notes to Head, Grace “was to look like a piece of Dresden china, nearly untouchable.” Head didn’t disappoint, sending Kelly out in a series of six polished outfits from a pleated little black dress to a gorgeous pistachio-green trouser suit complete with a white silk halter-neck. The absolute scene-stealer, however, has to be the black fitted, V-neck bodice-white full New Look style skirt-white chiffon shawl-pearl choker ensemble, which Lisa declares is “right off the Paris plane.”

Mahogany, 1975
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Ultra-kitsch, yes, and probably neither the best storyline or acting you’ll see on screen, but Mahogany remains as entertaining now as it was when it was made in 1975, telling the rags-to-riches story of Tracy Chambers – played by Diana Ross – a style-conscious department store secretary who rises to fame as a model in Rome (and changes her name to Mahogany) before becoming a fashion designer. Directed by Berry Gordy, Mahogany coincided with a wave of African-American models and designers gracing the runway, from the original black supermodels Donyale Luna and Iman, to Scott Barrie, Patrick Kelly and Stephen Burrows – and the film brilliantly reflects the glitz and glamour of Seventies fashion. By day, Tracy channels wide-brimmed hats, jersey dresses and knee-high boots; at night the lamé, sequins, rhinestones and feathers come out in force. Interestingly, many of the outfits were designed by Ms Ross herself, who had studied dressmaking and, in the early days, made the Supremes’ costumes. With haute couturier Princess Irene Galitzine also on board as a designer, this is bold and overstated Seventies at its best.

Main image: In the Mood for Love
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