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

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

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...

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Bob Dylan - Sunglasses inside

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

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.

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David Beckham - Double denim

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.

Bryan Cranston - Shaved head through choice

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.

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Charlie Casely Hayford - Boots with tailoring

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

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

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

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.

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Lionel Richie - A moustache

Just imagine Lionel Richie without a moustache.


Go on.


Imagine it...

Steve McQueen - White jeans

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.