These are the most stylish films in history

Lights! Camera! Fashion! Who doesn’t love a good old fashioned trip to the cinema? We know we do. But, while most of us head to the movies for a bit of entertainment or escapism, others look to the silver screen for inspiration. Costumes and wardrobing in films can be just as influential and important as other elements, such as scripting and casting. In fact, there’s been an Oscar awarded for best costumes since 1949.

Which got us to thinking: which pictures, in those intervening years, have had the most notable impact on our wardrobes? Which are the most trimly-tailored, bold and daring, fashion-forward films in history?

Starting strongly, this early noughties trilogy brought as much style to the multiplex as it did swagger. Assembling a dream team of Clooney, Pitt and Damon wasn’t enough for director Steven Soderbergh — and he spent all three instalments dressing his heisters and hustlers in threads fit for a con-man king.

The lapels are so wide they span US states, Elliott Gould’s specs are so huge you could fit a face in each lens and Don Cheadle wears so many silk scarves we almost, almost forget about his terrible British accent. And Brad Pitt’s entire wardrobe? Don’t even get us started. Boundary-pushing, blindingly good and big, big, big on everything.

It’s mods versus rockers! And, with such a cinematic showdown, each side had to have a strong visual identity. Enter some of the sharpest pinstripe suits and skinniest ties on Sting’s side, and more black leather, studs and sunglasses than you can shake a Lambretta at in the biker’s camp.

We’d also like to give Quadrophenia’s hat game an honourable mention. Set at a time when the humble hat was still clinging on, this 1979 film shows just how stylish a head-topper can be with the right outfit. Next time you give it a watch, you’ll be reaching for your trilby in no time.

Set in the 1980s on Wall Street — now there’s another film with great style — American Psycho is the gold standard of yuppie chic. Christian Bale’s bold striped shirts, contrast collars and thick braces are tightly secured in the annals of movie-style fame with a Double Windsor and shoulder pads so chunky he looks like a linebacker.

In fact, everybody Bale’s anti-hero Patrick Bateman works with in the city has a similarly enviable wardrobe — especially Jared Leto’s ill-fated Paul Allen. And true, the suits may look boxy to us today, but wear them with enough arrogance and self-importance and they’ll come off as timeless. And, if that fails, just throw a long raincoat on over the top and face your detractors axe-on…

In another whirlwind of 1980s style, Luca Guadagnino’s Oscar-winning romance should give its costumes equal billing alongside stars Armie Hammer and Timothee Chalamet. From loose polo shirts billowing with insouciance to some of the most covetable swim shorts to ever take a dip in the Med, it’s an Italian-set paradise for the sartorially minded.

Particular praise must be heaped on Hammer, who takes short sleeved shirts and makes them look not only coolly casual — but also utterly desirable. Pair these button-downs with his shortest of short shorts and his folding Persol sunglasses, and you’ve got a ready-made silver screen style icon.

Ah, Steve. We’ve been expecting you. McQueen brought style, suaveness and sex appeal to all of his roles — and his signature three-piece suit in The Thomas Crown Affair or informal trackside duds in Le Mans could just have easily have landed him on this list. But there’s an edge to Bullitt that sneaks it ahead.

Not only does Lieutenant Frank Bullitt’s wardrobe still hold up over 50 years later — The turtlenecks! The chukka boots! The rain mac! — but it also perfectly conveys just how rough, ready and utilitarian McQueen’s character actually is. It’s a twofer; introducing serious style and furthering our understanding of the character. Bravo.

No, not the Leonardo DiCaprio one — although Baz Luhrmann’s version did button up some very natty threads, too. Rather, we’d still plump for Robert Redford’s take on F. Scott Fitzgerald’s most famous creation. Redford’s Gatsby may look bold and brash in his colourful suits, but his performance tempers the wardrobe — and renders it endlessly more believable.

And, boy, we’re glad it does — because there are some seriously impressive suits on show. Whether white and three-piece with a double-breasted waistcoat, dusky pink and paired with a baker boy cap or just one of the most neatly trimmed white tie tuxedos we’ve ever clapped our peepers on, this film is the only tailoring inspiration you’ll ever need. Oh, and Redford’s Gatsby also wears the hell out of a cable-knit cricket jumper.

Guy Ritchie can be a little hit and miss. True, he has served up some excellent sartorial screen moments, but much of his schlocky gangster oeuvre is so stuffed with pork pie hats and gold necklaces that you can hardly see the plot. Thank the designer lords, then, for The Man from U.N.C.L.E. And, once more, for Armie Hammer’s impressive frame on which to hang some colossally good clothes.

Both Hammer and Henry Cavill — whose frame is similarly superhuman — wear sharp mid-century suits for much of the runtime. But the duo’s tactical gear is what really draws our attention. A turtleneck, dark jacket and flat cap? It’s early-Bond spy style, and we’re all for it.

A whole ten years before Pretty Woman, Richard Gere made a sartorial splash in American Gigolo. This film also marked the first major introduction of Giorgio Armani clothing into Hollywood. Everything Gere wears — or doesn’t wear, as the case may be — is drenched in European style, from his underpants to his overcoat.

And oh, what an overcoat it is. The striking image; one that has since become synonymous with the film, sees Gere enveloped in Armani’s camel-hair polo coat, belted around the middle and with a cigarette hanging from his mouth. Under it, his shirt has a collar so pointed you could cut yourself on it and a tie so 1980s you can almost hear Blondie singing. An enduring look.

Martin Scorsese’s 1995 gambling masterpiece is as big and brash as the city it’s set in. Swanning around Las Vegas in fur coats and garish colours, messrs De Niro, Pesci and Stone are the epitome of mid-seventies sleaze. And we love it. Never have more lurid shirts been worn underneath such grey suits — but, somehow, it works.

The supporting cast, too, have their fashion moments. James Woods shines as a con-artist-turned-pimp called Lester Diamond — although not as brightly as his all-white, epauletted leather get-ups. And Joe Pesci’s neckwear? You can hardly tell whether they’re ties or cravats the things are so silky and huge. But that’s Casino: the wardrobe on this film was the essence of excess, tailored trimly into some truly love-hate suits.

Possibly the best-dressed film on this entire list — and it doesn’t even look like it’s trying. Starring Matt Damon and Jude Law, this 1999 thriller jets around the globe, darts from perilous situation to perilous situation, and moves at a breakneck speed, but oozes a casual carefree air — all thanks to its well-curated clothes.

This is as nonchalant as wardrobing can get. Whether it’s a slightly baggy blue button-down, a knitted bowling shirt or a pair of white slip-on moccasins, Damon and Law are still influencing low-key summer dressing from the other side of the millennium. And long may they continue to do so…

Have muted colours ever looked so stylish? In Spike Jonze’s 2013 tragicomedy, Joaquin Phoenix gives a stellar, moustachioed performance as a man who falls in love with an AI assistant. But, as strange as that sounds, you won’t be able to concentrate on the plot — instead, you’ll be preoccupied wondering where he bought all of his understated, highly covetable shirts.

A mustard one here, a coral one there, a sky blue patch-pocketed one if you fancy it. The man has so many subtly-coloured, slightly loose button-downs that he could give Robert Redford’s shirt-chucking Gatsby above a run for his money. He also wears a damn good trapper hat at one point — and that’s a hard look to pull off.

Well, there had to be a Bond film on here at some point, didn’t there? It was a toss-up for us between Daniel Craig’s seminal Skyfall and Roger Moore’s The Man With the Golden Gun. But, while both see their respective superspy dressed to kill, it’s Skyfall’s sartorial treatment of its supporting cast that swings it for us.

Yes, Craig may look great in a greatcoat — and perfectly rugged in that Barbour jacket he shrugs on in Scotland, but we can’t overlook Q’s natty cardigan, the new M’s double-breasted duds or the villainous Silva’s Spanish-flavoured suiting. There’s wardrobe inspiration here for all — no matter which side you’re on…

Want more from the glitzy world of the silver screen? Here are the best Hollywood memoirs to read now…

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