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11 Times Someone Famous Broke A Style Rule... And Won

The celebrities who laugh in the face of society's sartorial rules

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As the rules of men's style seem to grow ever more fluid with each passing season, there are still some get-ups that most would be loathe to try - unless you're a celebrity of course.

Here we break down the 12 times a famous person shunned the written and unwritten laws of style, yet came out on top anyway.

Oh to be rich, famous, adored and able to wear whatever the hell you want...

Bob Dylan - Sunglasses inside

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Sunglasses worn anywhere without sunshine may now be popstar pastiche, but Bob Dylan's been carrying it off for decades. And while even the most high profile of men typically come across as complete tw*ts when they wear shades inside - we're looking at you Bono - Dylan's culture god status and give-a-shit aura marks him out as a special case.

Andre 3000 - White dinner jacket

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As Esquire's Deputy Style Editor Charlie Teasdale says of the white dinner jacket: "Few of us can go full KFC colonel and get away with it." But then again few of us are Andre 3000, hip-hop's king of dandy style and one of the most effortless dressers in the business... any business.

David Beckham - Double denim

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Double denim may no longer be the terrible taboo of menswear it once was, but that doesn't mean it's an easy one to pull off. Yes, David Beckham is a tricky man to emulate, but you can still follow in his footsteps and get it right by steering well clear of any form of matching denim, lest the blue god of acid wash '80s Hasselhoff be unleashed upon ye.

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Bryan Cranston - Shaved head through choice

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The ultimate grooming power move, an unforced shave of the head separates the men from the boys, with Bryan Cranston the king of the buzz after his time spent playing cancer-stricken meth magnate Walter White in Breaking Bad. It's a lucky man who looks better without hair than with it, but Bryan's one of them.

Charlie Casely Hayford - Boots with tailoring

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The previously unyielding rules of tailoring may have softened in recent years, with trainers now welcome inside the club house, but military boots and formalwear are still seen as a big no-no. Unless of course you're London tailoring royalty Charlie Casely-Hayford, a man who has made 12-eyelet commando boots, cropped trousers and double-breasted jackets a winning signature look.

David Bowie - Any kind of hat

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Post-JFK, any hat that isn't of the baseball variety marks you out as a terrible wannabe try-hard. But then there's Bowie: the pop culture shapeshifter whose style and sound metamorphosed with each passing decade. And a man who looked bloody great in any hat.

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Jeff Goldblum - Leather jacket past the age of 30

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Disregarding the porkpie hat (which he also manages to wear well) the fact that Jeff Goldblum at the age of 63 can rock a leather jacket better than the vast majority of guys a third of his age marks him out as something of a menswear marvel.


Teach us, Jeff.

Jimi Hendrix - Black shirt

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We've spent plenty of time deriding the favoured shirt colour of the 'Lad on a night out™', but when it's worn under blue velvet and by one of the chief hedonists of the 20th century, well, it's quite hard to fault really.


Milton Keynes Weekend Warriors take note.

Lionel Richie - A moustache

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Just imagine Lionel Richie without a moustache.


Go on.


Imagine it...

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Steve McQueen - White jeans

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Unless you're an Italian powerboat racer, then white jeans are a completely unacceptable item of clothing to use when covering your legs. But then we look at this picture of Steve McQueen and we begin to question everything that we've ever held dear, because - undeniably - he looks fantastic.

Jared Leto - Everything

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Having gone into big screen hiding post Suicide Squad, we sort of miss Jared Leto's ever more elaborate attempts at tearing up the red carpet rulebook. This all-Gucci, all-bright, all-Leto get-up is actually one of our favourites. With so many men dressing like beige graphic designers nowadays, it's quite refreshing when a guy takes a massive swing at a look and, in our opinion, pulls it off.

Headshot of Finlay Renwick
Finlay Renwick
Deputy Style Editor
Mother, blogger, vegan, model, liar
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