As Western wear continues to ride high in the style stakes, we look to six iconic outlaws for sartorial inspiration. Leather chaps optional.

The clothes that traditional cowboys wore were almost as important to them as the horses they rode and the saddles they used; they were the tools of the job. Durability is a quotidian virtue but it’s vital when it comes to workwear and it has an unintended benefit: most clothes look and feel better as they get older. The rugged fabrics from which Western wear is made (denim, suede, chambray and bridle leather) all benefit from a sustained period of hard use, whether that’s achieved sitting in a horse’s saddle, a motorbike seat or even an office chair.

These rugged fabrics were chosen with more important considerations in mind than their appearance but the reason we’re still wearing various forms of Western wear a century after it was developed (a few years ago Levi’s offered 1915-replica 501s) is that it looks so good. And while each element is individually right, the combination is sublime thanks to the mix of textures and colours. The contrast between the sheen of brown leather boots and the fuzzy blue denim of a pair of jeans, for instance, is unbeatable. And the colour combination of indigo jeans and a pale-blue chambray shirt is just as pleasing. But give these clothes a year or two of sustained wear and they’ll look even better – over time, denim moulds to the body in a manner reminiscent of leather, while chambray shirts soften up and their colour gently fades.

Looking over these shots from Hollywood’s distant golden age we’re reminded that Western wear is always relevant, so wherever your clothes are on their long life-cycle of purchase, wear, soften, fade, fray and finally – regretfully – replace, they’ll never be wrong.

Much has changed since Mr Elvis Presley made his movie debut in Love Me Tender, not least the idea that any young singer could be sufficiently famous to take the starring role in his or her first film. Love Me Tender (so named to cash in on Mr Presley’s hit single) is a drama set during the American Civil War and features the singer as the youngest of four brothers. The film, which was very much a vehicle for the singer, surprisingly concludes with the shooting and burial of his character and, arguably, the film dealt a similar fate to Mr Presley’s ambitions of becoming a serious actor. However, although the life of his character, Clint Reno, was cut short, Reno’s style lives on. Mr Presley, photographed on location, looks every inch the star in his rugged work shirt (with the collar popped to keep the sun off his neck) and a taupe felt hat.

Easy Rider, Mr Dennis Hopper’s 1969 directorial debut, was such a success that Universal Pictures gave him $1m and creative carte blanche for his second film, which was confusingly titled The Last Movie. The plot sees Mr Hopper playing a man called Kansas, a washed-up stuntman living in Peru, where he’s been filming a cowboy movie. Kansas discovers the native people are pretending to make a film but engaging in real violence instead of stunts during the action scenes. If the plot – and the questions it sought to ask about the duality of fiction and storytelling in cinema – was largely lost on the film-going public, it takes nothing from Kansas’ style. Although Mr Hopper appears here behind the camera, he also starred in the film, so his double-denim outfit (and we can probably assume that it’s actually triple-denim) is part of the character’s costume. These clothes make us wonder if it might not be time to buy an unwashed denim trucker jacket and wear it until it’s in tatters (and how cowboys’ hats stay on their heads when they’re riding).

Giant is best remembered as a film starring Mr James Dean, released after his premature death in a car accident. However Mr Rock Hudson and Dame Elizabeth Taylor also played lead roles in this drama about life among the oilfields of Texas and the way those at the top of that society treated those at the bottom. The film’s expansive locations are an important part of its appeal and, in this shot, Mr Hudson looks entirely at home on the back of a horse amid the Texan landscape. His leather chaps only work because he’s in the saddle but the blue jeans and cowboy boots could have come from the latest Saint Laurent collection (although the Saint Laurent jeans are cut rather closer to the body). The urban equivalent of Mr Hudson’s horse is a single-speed bicycle but pedalling around London’s Peckham or New York’s Lower East Side doesn’t quite have the romance of riding around a Texan ranch and in any case it would be hard to keep your cowboy boots on the pedals. Style and practicality so rarely go hand in hand.

Back to The Misfits, and into the back of Mr Clift’s car. Here the actor looks pensive with his dark, heavy eyebrows expressing great concern about something. Quite what he had to worry about while filming under the direction of the great Mr John Huston – and with Nevada’s extraordinary landscape behind him – is lost from memory. It certainly wasn’t his shirt, which is an unusual white, snap-button Western number with a particularly lovely collar roll. It’s an outfit that reminds us to wear a casual white shirt (perhaps an Oxford cloth button-down) much more often, paired with blue jeans and sunshine.

Cool Hand Luke remains a 1960s rallying cry for men of indomitable spirit to take on a cruel and heartless system, in this case a Florida prison. However the film’s eponymous hero, Mr Newman’s Lucas “Luke” Jackson, is ultimately broken by that system. Despite its sad ending, the film suggests that life on a Floridian chain gang was more amusing, and picturesque, than seems plausible – this is a movie that makes back-breaking work look very stylish indeed. This location shot of Mr Newman scanning the film’s script (adapted from a novel by Mr Donn Pearce) reminds us to concentrate on our posture, hang onto our jeans until they’re threadbare and to consider (we’ll put it no more strongly than that) whether we could sport a singlet on holiday this summer.

Few rock’n’roll stars have so consistently exhibited a reckless, outlaw spirit as Mr Keith Richards, founding member of the Rolling Stones – and his clothes have always followed suit. Mr Richards’ mischievous behaviour has taken many forms over the years but this shot records the period when his band had left the UK for France in order to put themselves beyond the reach of the tax authorities, and to record their classic 1972 album Exile on Main St. Among the famous visitors to Villa Nellcôte was the country singer Mr Gram Parsons, and Mr Richards was perhaps inspired by Mr Parsons’ flamboyant clothes (many of which were produced by “rodeo tailor” Mr Nudie Cohn) when he decided to wear this lavishly decorated Western shirt.