Denim is the fabric of rebels, rockers and ranchers. Why not take a few style tips from those who have worn it well in the past?.

It began as 19th-century workwear, assumed pop-cultural omnipotence on the backs (and legs) of Messrs Marlon Brando and James Dean, and today reigns unchallenged as a wardrobe perennial. Denim conquered the world from rockers to runways, from blue-collar to red selvedge, and from Hollywood to high street. But while it might have been designed as the go-to utilitarian material, not all denim-wearers are created equal. As the menswear catwalks confirm that the indigo-dyed cotton staple is once again indubitably on-trend, we round up those denim icons who wore it better than anyone, and who even turned the potentially calamitous double-denim option into a triumph of the twill.

“Jack the Dripper” (as LIFE magazine christened him) is the most celebrated proponent of denim in the studio, darting round his floor-splayed canvases in Lee jeans, heedless of the oils arcing from his brushes. The result? A paint-splattered uniform every bit as abstract expressionist as his acknowledged masterpieces. Mr Jackson Pollock’s sartorial inspiration was Mr Pablo Picasso, who painted in denim overalls, and not just in his Blue Period. Mr Pollock then went on to influence artists as various as Messrs Max Ernst and Andy Warhol (who sported similar studio-fresh garb), and Helmut Lang and Martin Margiela (who produced garments that came pre-splattered, so their wearers could look the creative part without any tiresome throes-of-creation mess).

Mr Cary Grant’s greatest gift as an actor and all-purpose icon was his air of breezy nonchalance – who else could have outflanked the evil machinations of a crop-spraying plane while keeping his savoir faire and his immaculate Kilgour suit intact? So it’s no surprise that his off-duty attire should be as understated as his more formal ensembles. In fact, Mr Grant once wrote to Levi’s, advising the brand that if it ever evolved “a line of absolutely plain un-checked, un-metal-threaded, absolutely solid-coloured shirts... I will rush to the nearest store.” He got his wish; a garment as timeless and as unflappable – whether layered beneath woollens or softening plaids or pinstripes – as the erstwhile Mr Archibald Leach himself.

“Oh, Blue Jean,” sang Mr David Bowie in the song of the same name, “is heaven any sweeter than Blue Jean?” Not, he might have added, if the Blue Jean in question is as versatile a signifier as its wearer, who in the late 1970s managed to conjure a post-glam, proto-punk, neo-skinhead vibe (the forthright straight-legs, the chunky turn-ups), while anticipating the vogue for selvedge and workwear fetishism (the raw indigo with the plaid shirt and chukka boots). In fact, the blue jean and Mr Bowie are the perfect match – restlessly protean, always newly relevant, perennial cultural touchstones of creativity and rebellion. Jean genius, in fact.

Mr Hopper was an Actors Studio contemporary of Mr James Dean and a fellow early-adopter of outlaw denim. But as the counterculture metastasised in the late 1960s and early 1970s, and Mr Hopper cornered the market in bug-eyed rebel roles from Easy Rider to The Last Movie, he found himself taking the look into new realms, from cattle baron’s bad-seed son to badass-but-buttoned-up California biker. It also happens to be a look that couldn't be more achingly contemporary, from the craft beard to the crisp twills favoured by today’s Americana-inspired Japanese labels. “Do you know that ‘if’ is the middle word in life?” asks his crazed photographer in Apocalypse Now. Similarly, “Den” is the first syllable in denim.

Workwear and presidents have made uneasy bedfellows, and while we pride ourselves on being non-partisan one could make the case that Republicans (think President Theodore Roosevelt) wear it better than their Blue State rivals. (President Bill Clinton’s off-duty attire included baggy stonewash jeans that went way beyond normcore; President Barack Obama was derided for the “mom jeans” he wore to the 2009 MLB All-Star Game.) If President Ronald Reagan was alone in getting it triumphantly right, it’s because he’d starred in his share of Westerns and owned a 700-acre California spread. He reinvested denim with its original pioneer spirit, whether corralling Arabian steers, clearing brush, or chopping wood for the stove. Urban cowboys from Greenpoint to Shoreditch should roll up their chambray sleeves and follow his presidential lead.

Jeans with a jean jacket is a tricky concept to pull off – Mr Justin Timberlake’s tailored ensemble at the 2001 American Music Awards still elicits Sideshow Bob shudders. But no one did it better than Mr Martin Sheen in Mr Terrence Malick’s 1973 movie Badlands. He did it with swagger: as multiple murderer Kit Carruthers, he channels Mr James Dean channelling Mr Charles Starkweather, the real-life serial killer on whom his character is based. He did it with commitment: the scene where he “flips” his Levi’s “Big E” 507XX jacket over his head and onto his back is justly revered. And, most importantly, he did it with a simple white tee and Panama hat.

“Don’t you know how sweet and wonderful life can be/ I’m askin’ you baby, to get it on with me,” purred Mr Marvin Gaye on 1973’s Let’s Get It On – the “it” referring, of course, to his masterful denim shirt/ jean ensembles accessorised with bright red beanies, symbolic both of the sexually and politically charged climate of the era, and of Mr Gaye’s own liberation from the restrictive suits of his Motown apprenticeship. And if you want to stop beatin’ round the bush and get it on yourself, follow Mr Gaye’s lead by mixing up the fabric weights and colour rinses, perhaps adding a blazer to pull everything together.

Way, way back, long before Mr Mickey Rourke made his comeback in The Wrestler, he was outshining his Brat Pack peers by keeping things enigmatic, both with his Method mumblecore delivery and his understated, Harley-ready Western jackets. He played the Motorcycle Boy in 1983’s Rumble Fish, and lived up to his billing by leading a Hollywood biker gang that included the late action director Mr Tony Scott. “He spearheaded a whole biker denim revolution when he got out to LA,” claimed Mr Rourke’s friend and hairstylist Mr Giuseppe Franco. And who wouldn’t have wanted to don their darkest Lee Coopers and ride in his slipstream along Mulholland and Melrose?

If adopting top-to-toe denim is indeed once again becoming a thing (as the autumn/ winter 2015 shows would indicate), no one will be cited as mood-board inspiration more than Mr Robert Redford, whether playing the wrangler in any of his numerous horse-whispering roles, or sporting the Wranglers (along with the aviators and the boots) when home in Utah’s Wasatch Mountains. In the otherwise eminently forgettable Little Fauss and Big Halsy (1970), even the redoubtable Ms Lauren Hutton finds herself in a swoon over Mr Redford’s perfectly-weathered, impeccably rugged rig – all double-stitched, five-pocket, raw-selvedged, blue-eyed soul.