20 retro Hollywood icons you should be taking style tips from

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Deborah Cicurel
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While the likes of George Clooney, Chris Hemsworth and Idris Elba are all well and good, there's something about an old Hollywood film star that just tugs at our style heartstrings. Whether it's the abundance of pressed suits or the lack of flashy trainers we're not sure, but the understated elegance of the best retro Hollywood icons is something that seems to be from a bygone era.

We take a nostalgic look at 20 of the most stylish Hollywood legends - and their excellent sartorial choices.

  • Cary Grant

    Whether he was emerging from the sea in To Catch A Thief, running away from planes in North By Northwest or sporting a leopard print dressing gown in My Favourite Wife, Cary Grant always looked impeccably well-dressed and impossibly dapper. No one could work a high-waisted trouser quite like Archibald Leach.

  • Frank Sinatra

    Polka dot bow ties, sailor suits and pirate costumes: in his varied film roles, Ol' Blue Eyes was required to wear the most ludicrous of outfits - yet he still managed to look almost as good as he sounded. 

  • Marlon Brando

    In A Streetcar Named Desire, Brando proved that all you really need to be a timeless pin-up is a very tight T-shirt - and lots of testosterone. 

  • Gene Kelly

    If there's one lesson we can learn from history's best tap dancer, it's that decades of sports clothing companies have been conning us. Just look at Summer Stock, An American In Paris or Singin' In The Rain, and you'll see that it's perfectly easy to pull off the most athletic of movements wearing a sharp three-piece suit - there's really no need for trainers, lycra or a Fitbit. 

  • Louis Armstrong

    The raspy-voiced crooner made several film appearances with his trusty trumpet under his arm - but when we weren't marvelling at his musical talents, all eyes were on his variety of debonair suits. 

  • Humphrey Bogart

    Years before Pharrell ever appeared on the scene with his giant Sorting Hat, Casablanca star Humphrey Bogart was giving us all a masterclass in how to make headgear look as important as trousers. 

  • Clark Gable

    In his role in Gone With The Wind, Gable was able to say the most famous line in film history: 'Frankly, my dear, I don't give a damn'. But in our opinion, Gable should also be just as (or nearly as) well-known for the impeccable dress sense, perfectly slicked back hair and preened moustache that he sported in the epic. 

  • Clint Eastwood

    We have a sneaking suspicion that if we tried this poncho-cum-gilet get-up, we'd look rather silly. But then maybe that's because Clint Eastwood, even as the 85-year-old legend he is today, is more stylish than we'll ever be.

  • Alain Delon

    In Plein Soleil, Delon proved that you can be villainous, treacherous and evil, and no one will really mind - as long as you sport some great suits while you're doing it. 

  • Anthony Perkins

    You may remember him as the creepy villain from Psycho - but when he wasn't wearing wigs and his mother's old clothes, Anthony Perkins strutted his way through film sets wearing trench coats, short shorts and even this inexplicable suit jacket, which we suspect wouldn't have quite the same effect if we wore it to the pub, but we admire him for wearing anyway. Moral of the story: don't be afraid to try new things. Even if they are green and stripy. 

  • Fred Astaire

    The incredibly dapper star could give many a tracksuit-wearing modern gentlemen a lesson or two in how to pull off a Top Hat, White Tie and Tails with class and grace.

  • James Dean

    He died young, tragically young, but in his short life the Rebel Without A Cause star managed to make bomber jackets, sensible jumpers and plain white T-shirts look cooler than anyone has made them seem since. 

  • Robert Redford

    The Hollywood stalwart wore many a strange costume in his long career - but when a man can make a bushy moustache look as a good as this, you know he's a style icon for a reason. 

  • Gregory Peck

    In his simple shirts, tailored suits and always-impeccable hair, Gregory Peck taught us so many style lessons - including how to work thick specs in To Kill A Mockingbird. 

  • Sidney Poitier

    Whether he was dressed down in a simple T-shirt, relaxing in an old cardigan or suited and booted in a tuxedo, Sidney Poitier always looked dignified and elegant.

  • Paul Newman

    In his huge variety of acting roles, Newman had to sport togas, cowboy gear and headscarves - but he looked most suave of all when wearing one of his many polished suits. 

  • Woody Allen

    An unlikely icon, the self-deprecating comedian was an early pioneer of geek chic with his oversized glasses, nervous expressions and large collection of thick jumpers. 

  • Bing Crosby

    Never far from a microphone, cigar and beautiful leading lady, crooner Bing Crosby competed with the likes of his co-stars Grace Kelly and Dorothy Lamour for Best Dressed with his distinguished wardrobe.

  • Elvis Presley

    The King isn't everyone's style cup of tea - but those men wanting to make a fashion statement could definitely learn a lot from Elvis's glitzy get-ups and gyrating ways.

  • Montgomery Clift

    Star of A Place In The Sun, The Misfits and From Here To Eternity, Clift was known for portraying "moody, sensitive young men" - moody, sensitive young men with great clothes, that is. 

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Deborah Cicurel

Deborah Cicurel

Deborah Cicurel is a freelance journalist who writes about everything from lifestyle and travel to fashion and entertainment. She loves spicy maki rolls, cosy socks and visiting far-flung destinations, and is unable to walk past a dog on the street without stopping to befriend it. 

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