The most stylish male movie characters of all time

Since the Sixties, men’s style has changed dramatically. Successive youth cultures have combined to gradually relax the rules of formal attire and revolutionise how chaps dress. And yet, perversely, arguably the most stylish man on film in the last 50 years is one that is governed by the conventions of yesteryear. His name? Bond. James Bond. If you don’t find his elegance utterly bewitching then you’re probably a hipster bore. Or a Goth But not both.

The end of the Nineties was a troubling time for men. We were constantly told that we were on the way out. Then, thankfully, just as this emasculation by proxy reached fever pitch, along came Tyler Durden. A man with war in his soul and an idiosyncratic take on clothes. Part slacker madness, part punk bravado, his style summed up the meandering nature of the last decade of the 20th Century. And that leather jacket rocked.

Let’s play a quick game of word association: cowboy… Now, if you didn’t close your eyes and immediately bring to mind Clint Eastwood’s iconic character in Sergio Leone’s Dollars Trilogy then you need to have a long hard look at your life. Eastwood’s drifting cowboy is the quintessential outsider. His functional dress sense embellished by a raft of stylish accoutrements – cigarette, beard, hat, poncho etc. This man knows how to turn a generic look into something memorable. Not an easy task.

Patrick Bateman is misguided in almost every facet of his disordered existence. Except for one: his slavish attention to dressing with a certain enviable flair. Christian Bale’s performance as the bloodthirsty counterpoint to Gordon Gekko is utterly compelling. To paraphrase Spider-Man: with immaculate grooming comes great responsibility. Bateman ignored this maxim at his peril. He did look remarkably classy though.

In the lexicon of cool there are many pretenders to the throne, but there is only one King. Despite being committed to celluloid nigh-on 50 years ago, we are still worshipping at the altar of Frank Bullitt. Steve McQueen invested his unfussy style into the taciturn detective and that winning mixture of clean-cut Ivy League design and sharp mod flair remains a key male fashion signifier. As the saying goes: women want to be with him, men want to be him. Enough said.

If Jude Law hadn’t cracked this movie lark, he could have become a male clotheshorse, such is his spotless handle on looking good. The role of foppish playboy Dickie Greenleaf in The Talented Mr. Ripley was, ahem, tailor made for him. Greenleaf is the archetypal Fifties natty dresser. A dash of Ivy League style complemented by a generous helping of relaxed modernism. It’s a look that remains fresh today.

As the inclusion of other less savoury types in the list attests, you don’t have to like these characters, only be bowled over by their stunning and unique sense of style. Tony Montana is one such figure. A self-made man from the streets, his guiding principle is flash ostentation and aggressive power. This equates to some interesting clothes – the Hawaiian shirts, his shirt collars – but, like the man himself, you always know he’s around.

Some cinematic characters could sport a Justin Bieber T-shirt, Day-Glo shorts, lurid socks and the most granddad sandals imaginable, and still look stylish. Jules Winnfield is one such man. Thanks to the innate nonchalance of Samuel L Jackson, Winnfield exuded charm, class and cool. Yes, he carried off the suit with unruffled calm, but following a blood splattered accident in the back of the car, he was still composed in a garb not too dissimilar to that outlined above.

Whether you watch the Robert Redford version of Gatsby or the more recent Leonardo DiCaprio it's no secret that Jay Gatsby has got bags of style. Smart suits - both pinstripe and cream - pastel hues and more than a hint of salmon. Even if he's empty inside, his outside looks stunning

Gentlemen; if you're weary of the contemporary preference for all things ‘dude’ –and aspire to be a ‘proper’ man: rugged, silent, funny, tough and possessed of a magnetic appeal to members of the opposite sex, take our advice: watch Humphrey Bogart in The Big Sleep. That is all. Just watch and learn. Old school machismo and ripe for revival. Do it.

Private detectives are cool; the colour black is cool; leather is cool; funk music is cool; New York in the early Seventies was cool. Put these five ingredients together and you’ve got an irresistible and stylish mix. Dressed all in black leather, John Shaft was ready for business. Can you dig it?

If you’re between 20 and 30 and you don’t want to ape the calm indifference of Ryan Gosling’s Driver then there’s either something seriously wrong with you or you’re an aspiring Conservative MP, in which case our point still stands. His near silent appearance isn’t a mask for blankness, his still waters run very deep. We live in almost ridiculously emotional times – his reticence to engage should be admired as a badge of honour. As for the clothes, well, just look at that jacket for starters…

He might have epitomised the worst traits of modern capitalism (his mantra was, after all, ‘greed is good’ – a maxim still fully functional today it would seem), but even the most fervent anarchist revolutionary would have to concede Gordon Gekko looked stylish. His look was all about power, indeed the phrase ‘taking care of business’ could have been coined for him. If you’re going to be a greedy, reprehensible bastard, at least carry off Gekko’s visceral authority.

Julian Kaye (Richard Gere) is a vacuous, arrogant, narcissistic male escort. He also happens to be the best dressed, most stylish, most physically appealing male escort around. Dressed head to toe in Armani – and thus heralding the allure of the designer-led Eighties – Kaye remains a provocative cinematic character. Preppy, clean cut and very American, he laid the groundwork for other vainglorious individuals from that decade including Patrick Bateman and Gordon Gekko.

Lounging around in a beaten-up T-shirt, well-worn jeans, battered sneakers and a grey hoodie that’s been stretched every which way, might not get you a place at the table of high fashion, but then, who wants to hang out with Anna Wintour anyway? Axel Foley is our kind of guy when it comes to slackerdom. Everything comfy and relaxed. The infectious attitude and beaming smile just add to the general beatific mood. Eddie Murphy’s finest moment.

The likes of Stanley Kowalski (A Streetcar Named Desire) and Johnny Strabler (The Wild One) might have rocked the T-shirt look before James Dean’s most notorious cinematic role, but Jim Stark popularised it and gave it a dramatic appeal to the burgeoning teen market in the Fifties. To this day, Stark’s ‘uniform’ – jacket, white T-shirt and jeans – denotes classic outsiderdom.

That Daniel Plainview is a certifiable nutjob goes without saying: in any other industry bar that which he excelled – getting filthy rich – he would have been an outcast. But he was stylish, you have to give him that. He oozed raw masculinity and was, in the immortal words of Lady Caroline Lamb, ‘mad, bad and dangerous to know’. Money might not have bought him manners or grace, but it did buy him a dapper wardrobe.

Again, we could have chosen either of the two leads in Tarantino's 10th movie but it's Leonardo DiCaprio's Rick Dalton that edges it for us. His iconic style is 'typical' 60s Hollywood, all roll necks and brown leather. It's a great look and one that DiCaprio effortlessly pulls off

In the aftermath of acid house, grunge and with Britpop poking its head above the aesthetical parapet, wearing a suit in the early Nineties wasn’t the most stylish look in town. However, thanks to Reservoir Dogs’s wisecracking, pop culture orgy, the simple pleasures of a black suit and white shirt were reborn. But who was the most stylish hoodlum in Quentin Tarantino’s gang? The deadly Mr Blonde of course: his macabre intensity and remarkable insouciance made for an unforgettable cinematic character and enduring fashion icon.

Breathless – or A Bout de Souffle to give it its correct title – is the nonpareil masterpiece of the French New Wave. Unsurprisingly, therefore, its protagonist Michel Poiccard best represents the values of this innovative and ultra cool medium. A petty criminal he might be, but Poiccard (played with relish by Jean-Paul Belmondo) is so effortlessly hip he puts the wannabes in Dalston to shame. His continental élan was a considerable forbear upon London’s mods and his look – easy going sophistication – still looks magnificent today.

As any member of the male species who’s ever cut some impressive rug on a dancefloor will testify, there’s nowt cooler in piquing the interest of the ladies. And to this day, the film character that embodies such playful power is John Travolta’s Tony Manero. From his gleeful peacock-like strut to his charming wardrobe, Manero was disco’s coolest mainstream icon. All together now: Well you can tell by the way I use my walk, I’m a woman’s man…

Although we don’t have any empirical research to back this up we’d imagine looking good is 50 per cent pleasing yourself and 50 per cent impressing other folk. Some people cannot live worrying about the thoughts of others. This in itself is very stylish. The Dude is therefore very stylish. Granted, Patrick Bateman wouldn’t have got much Wall Street action done lounging around in flip-flops, a dressing gown and a cable knit cardigan, but then an expensive suit is no good for bowling. Make of that what you will.

Beneath the clean cut exterior, Marty McFly was definitely a rebel in his own lifetime. Bored of the present day, he had the cojones to stand up and be counted. And you know what? He looked pretty fly (sorry) doing it. Today his plaid shirt, denim jacket and gilet combo is pretty much a multi-media wardrobe. And if that’s not stylish, we don’t know what is.

Despite his death 15 years ago, James Stewart remains cinema’s favourite everyman – he was famed for playing decent, hardworking characters to whom we could all aspire. Vertigo’s John ‘Scottie’ Ferguson was slightly different; a touch more complex and a lot more stylish. His jumper and shirt mix might have looked humble, but it dominates masculine dress codes to this day, and his suit and fedora combination was suitably old school. In 1989, the United States Library of Congress described Vertigo as being ‘culturally, historically and aesthetically significant’. The same description could be applied to the spellbinding, sympathetic and stylish Scottie Ferguson.

No-nonsense hardboiled detectives are ten-a-penny in Tinseltown. However, not all exude such distinctive fineries as Popeye Doyle. Not possessed of leading actor looks like his contemporaries Paul Newman and Steve McQueen, Gene Hackman revelled in this down-at-heel, everyman style. But what really set Doyle apart was his distinctive pork pie hat, the perfect accompaniment to his uncomplicated bellicosity.

It was always going to be the case that Colin Firth, as George, was going to be smartly dressed in A Single Man, given it's directed by Tom Ford but his character's dress sense is impeccable. The 60s style really suits Firth, with crisp white shirts, skinny ties and polished black Oxford shoes - Ford took control of the wardrobe and he does a superb job.

As Mad Men has latterly demonstrated, there is still a tremendous appetite among men for dressing sharper than a glistening sword. In Wong Kar-wai’s majestic dissection of romance and duty in 1960’s Hong Kong, the impeccable Tony Leung stars as the dutiful Cho Mo-wan. Chow is a journalist, but dresses like Cary Grant and has none of the morals of some of the more disreputable members of the Fifth Estate. He is a man to set your watch by. Suave, urbane and likeable. A proper grown-up in other words.

Before he sunk into a self-induced torpor, Howard Hughes was the coolest cat in Hollywood. Leonardo DiCaprio’s portrayal of the colourful producer and aviation pioneer was played to perfection, highlighting his many moments of stylish genius before succumbing to his manifold afflictions. With the likes of Kate Beckinsale (playing Ava Gardner), Cate Blanchett (Katherine Hepburn) and Gwen Stefani (Jean Harlow) hanging from his arm at various moments, Hughes certainly oozed sophistication.

The strong silent type is a much cherished movie trope, and Mickey Rourke played this to the hilt as the mysterious Motorcycle Boy in Francis Ford Coppola’s acclaimed Rumble Fish. A former delinquent whose reputation precedes him, Motorcycle Boy is worshipped by his equally demonstrative younger brother (Matt Dillon) and other teenagers searching for a role model. And while his attempts to go straight are thwarted by society’s straights, the legacy he bequeaths is sharp, stylish and meaningful.

There’s nothing glamorous about being a drug addict; but if anyone can still look stylish while enduring the daily travails of getting that next fix it’s Matt Dillon. He shone in Gus Van Sant’s breakthrough movie – his Bob Hughes could have been a hopeless loser in lesser hands, but he invested the character with a studied nonchalance. And as we’ve mentioned before, the man in black look is always a vote winner.

Not many people can make sportswear look cool, but Richie Tenenbaum does in The Royal Tenenbaums. Played by Luke Wilson, we are big fans of his Fila sweatband, well-kept beard and his addiction to retro cameras.

While viewed with typical disdain by the French establishment, gangster Jacques Mesrine was viewed in some quarters as Robin Hood-type man of the people. It was this provocative point of view that propelled Vincent Cassel’s portrayal of Mesrine in the eponymous two-part retelling of his life. A kind of glamorous revolutionary – an urban Che Guevara – his chic, very French and very Seventies look will no doubt inspire would-be outlaws down the ages.

We could have chosen either lead in the sumptuous Call Me By Your Name but we've opted for Timothée Chalamet's character Elio. Whether he's rocking double denim, a band shirt or some short shorts he looks fantastic in every scene.

Hip hop gave style a fresh impetus in the Eighties and nowhere was this better captured on film than in Spike Lee’s majestic examination of race relations in New York, Do The Right Thing. Lee himself played the film’s central character, Mookie, whose baggy, sports-inspired clothing was taken straight from the streets of the Five Boroughs. A potent look that continues to thrill to this day.

Inspired by the colourful exploits of David Bailey, Thomas, the duplicitous photographer at the heart of Michelangelo Antonioni’s bewildering exploration of swinging London, is dripping in panache. His sky-blue shirt and white jeans aesthetic is a post-mod favourite that has driven the work of designers down the ages. Thomas (played to perfection by David Hemmings) might not be the most likeable character on this list, but you would snaffle his wardrobe in a heartbeat.