The 10 Most Seminal Menswear Moments On Film

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Movie style icons. They’re everywhere. Dead or alive, their presence is felt in everything from wall posters to our wardrobes.

The big screen has that unique ability to make us want to wear something, imbuing a simple T-shirt with the spirit of rebellion, or a suit with world-class flair. I mean, let’s face it, we want our Cuban collar shirts to look as good as Dickie Greenleaf’s, and the ability to make a pack of fags concealed under a T-shirt sleeve look as good as Jim Stark did. Who wouldn’t?

Here’s our rundown of the 10 most formative style moments on film:

American Psycho (2000)

Christian Bale as Patrick Bateman

Sure, the guy might have been self-obsessed, emotionally detached and well, psychotic, but today’s metro man owes Patrick Bateman a thing or two. He made male grooming a thing with his exhaustive regime that included ice packs and facial masks, and his boxily-cut Italian tailoring nailed late 1980s menswear.

That’s not even to mention his effect on our business cards…

Christian Bale/Patrick Bateman in American Psycho

American Gigolo (1980)

Richard Gere as Julian Kaye

Part self-serving gigolo, part sartorial genius, Julian Kaye sported the Armani suit like no one else. In between satisfying clients, dabbing cocaine and lovingly setting out suits on his bed while deciding what to wear, Kaye rang in the era of big-name designers with enviable nonchalance.

Debuting a new (European) kind of tailoring that had Savile Row up in arms, he showed us that suits don’t have to be skin-tight to be stylish – and we’re still learning from him now.

Richard Gere/Julian Kaye in American Gigolo

Back To The Future Franchise

Michael J. Fox as Marty McFly

Sci-fi romp Back to the Future II predicted we’d all be wearing self-lacing shoes in 2015. We might not be quite there yet – although Nike‘s recently unveiled HyperAdapt 1.0 self-lacers are set to make good on the prediction when they drop the end of this year – but we are sporting smartwatches, Fitbits and other wearables worthy of McFly’s wardrobe.

Then there’s his trending outerwear (denim jacket, gilet), a fearless approach to bold colour and the fact that he time-travels in his Calvins.

Michael J. Fox/Marty McFly in Back to the Future

East Of Eden (1955)

James Dean as Cal Trask

It wasn’t all about that red jacket. As well as popularising the white T-shirt and Lee jeans in Rebel Without a Cause, James Dean made smart-casual dress cool at a time when menswear was strictly buttoned up.

Take, for example, his turn as Cal Trask in East of Eden, in which he immortalised preppy style in the form of a now classic V-neck jumper and Oxford shirt combo. A true style giant.

James Dean/Cal Trask in East of Eden

It Happened One Night (1934)

Clark Gable as Peter Warne

No one pulls off a moustache, hat and hooked eyebrow quite like Clark Gable did in Gone with the Wind, but it was his lack of undershirt in It Happened One Night that proved his most style-defining moment – sales of undershirts in America allegedly plunged after cinemagoers clocked he wasn’t wearing one in the film.

The lesson? Do grow well-manicured facial hair, do opt for a suit with wide lapels and don’t wear an under-vest (just in case you were planning on it).

Clark Gable/Peter Warne in It Happened One Night

The Great Escape (1963)

Steve McQueen as Captain Virgil Hilts

Racing car driver, motorbiker and effortlessly stylish actor, Steve McQueen was nicknamed the ‘King of Cool’ for a reason.

Testament to his way with clothes, we’re still wearing leather bomber jackets over 50 years on from his appearance in war epic The Great Escape, and iconic pieces like this are even named in his honour. (Which will happen to us too, obviously).

Steve McQueen/Captain Virgil Hilts in The Great Escape

Krush Groove (1985)

Blair Underwood as Russell Simmons

Based on the rise of Def Jam Recordings, Michael Schultz’s hit film captured the explosion of rap in the 1980s, beaming hip-hop style from street corners to screens the world over.

As Russell Walker (read: Russell Simmons), Blair Underwood teamed Adidas tracksuits with Kangol hats – both trends that were to sail through well into the 1990s, and one of which still dominates menswear’s current sportswear bent today.

Along with co-stars Run-D.M.C., The Fat Boys and Sheila E., Walker took urban style mainstream. Krushed it.

Blair Underwood In Krush Groove

Fear And Loathing In Las Vegas (1998)

Johnny Depp as Raoul Duke

Gold-frame yellow-lens aviators? Check. Bucket hat? Check. Garish Hawaiian shirt? Check. Always sky-high antihero Raoul Duke might not epitomise the concept of timeless style but his eclectic approach to dress offers a valuable a lesson in not giving a sh*t. Like Depp himself, Duke wasn’t afraid to experiment.

The takeaway? All you need to pull off statement pieces is guts. (And maybe a tab of acid.)

Johnny Depp/Raoul Duke in Fear and Loathing in Las Vegas

Dirty Harry (1971)

Clint Eastwood as Harry Callahan

Decked out in ribbed wool jumpers and Lacoste polo shirts off-screen, Clint Eastwood’s style typified the post-Ivy League preppy style of the 1960s.

He taught us how to do it ourselves as the ruthless Inspector Callahan in Dirty Harry, pursuing justice (and stopping at nothing) in a two-tone tie, burgundy V-neck jumper and tweed jacket combo that took 1960s prep and sent it hurtling into the 1970s. Not to mention inspired Guy Ritchie and the geezer trend some 30 years later.

Clint Eastwood/Harry Callahan in Dirty Harry

Dr. No (1962)

Sean Connery as James Bond

Hands down one of the most stylish men on film, Sean Connery set the bar high with his first outing as Bond in 1962.

And even though a lot has changed, including the cut of his suits (relaxed then, razor sharp now) and the tailor that makes them (Anthony Sinclair then, Tom Ford now) the central message hasn’t: a classic black tuxedo will always look good. Gadgets, guns and girls, however, are optional.

Sean Connery/James Bond in Dr. No.

Final Word

Do you agree with our nominees for Most Stylish? Or there are other on-screen style icons you’d rather see the spotlight shone on?

Call the shots below.

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