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FEATURE

OSCAR WINNERS' STYLE LESSONS

By Sarah Kershaw, 24 February 2017

It’s nearly Oscars time again, and while the likes of Arrival, La La Land and Moonlight square up against each other for Best Picture, and Ryan Gosling and Denzel Washington fight it out to see who’s 2017’s top dog, we’re delving into the archives to find the most stylish takeaways from past Academy favourites. 
Style lessons from Oscar Winners

Picture: Rex

The film: Annie Hall, 1977

What it won: Best Picture

 

Arguably everyone’s favourite Woody Allen movie, Annie Hall won big at the Oscars (Best Director and Best Actress awards backing up Best Picture). If we were giving out the gongs, though, they’d go to Diane Keaton’s wardrobe. Famously androgynous, it’s a symphony of 70s menswear staples – waistcoats, ties, white shirts and wide-leg chinos. 

Style lessons from Oscar Winners

Picture: Getty

The lesson: wide-leg trousers always win

 

This guy knows the enduring power of pale, wide-leg trousers to elevate an outfit. He’s taken tips from both Diane and Woody here, going loose, rumpled and white. Toned down and brought up to date with the dark canvas of a navy roll-neck and charcoal coat, it’s just the right side of Manhattan beatnik. 

Style lessons from Oscar Winners

Picture: Rex

The film: Brokeback Mountain, 2005

What it won: Best Director (Ang Lee)

 

Ang Lee’s heart-rending tale of two cowboys discovering their love for each other was a seminal moment in cinema. It was also a seminal moment in the promotion of good old-fashioned Western wear. While we don’t suggest you go straight out and buy a ten-gallon hat, Jake Gyllenhaal’s double denim is a trend we’re glad we don’t know how to quit. 

Style lessons from Oscar Winners

Picture: Getty

The lesson: double up your denim

 

Taking a more wearable approach to the Canadian tuxedo than Jake’s full cowboy vibe, this street styler’s chosen to mix up his tones. Dark grey skinnies and a classic blue shirt are paired with worker boots and a tonal indigo tee for a look that works just as well on campus as it would on Brokeback.

Style lessons from Oscar Winners

Picture: Rex

The film: The Godfather Part II, 1974

What it won: Best Picture

 

Look at Al Pacino here and tell us that’s not one hella cool gangster. Mafia boss Michael Corleone showed that crime does pay ­– in the fashion stakes, anyway – with his slicked-back hair, sharp-as-a-shank suits and that silk cravat.

Style lessons from Oscar Winners

Picture: The Urban Spotter

The lesson: keep your cravats close…

 

Take your own Italiano styling tip from this guy, who’s done away with the slickness of Corleone’s style but not lost the steez. His neckerchief lifts what would be a low-key outfit of utility staples, adding interest and colour. Bellissimo.

Style lessons from Oscar Winners

Picture: Rex

The film: The Graduate, 1967

What it won: Best Director (Mike Nichols)

 

If you’d have told us as kids that the kind of beige blazer our geography teachers wore could look cool, we’d have eaten our Von Dutch snapbacks. But, with Dustin Hoffman’s awkward Benjamin Braddock flying the flag for 60s normcore, a style legacy of dad staples now influences menswear’s finest. 

Style lessons from Oscar Winners

Picture: Getty

The lesson: here’s to you, normcore staples


Replace his polo shirt with a Supreme box logo sweat, and his straight-leg blue jeans with ripped black skinnies, add some Cobain-esque goggle glasses and a cross-body bag, and you’ve got this guy’s dadcore-meets-streetwear getup.

Style lessons from Oscar Winners

Picture: Rex

The film: Ray, 2004

What it won: Best Actor (Jamie Foxx)

 

The inimitable Ray Charles, as portrayed by Jamie Foxx, wore some jazzy suits. Too jazzy, maybe, for us to endorse here. But one thing you can absolutely take away from his on-screen wardrobe is his side-striped trousers – a micro-trend with which menswear’s highest echelons are currently in love. 

Style lessons from Oscar Winners

Picture: Getty

The lesson: a bit on the side is a good thing

 

It’s not confined to formalwear, either. The likes of Kanye, ASAP Rocky and Louis Tomlinson have been repping the tux-style detail on streetwear and jersey recently. Here, this stylish dude shows that it can work on denim and on tracksuits by mashing the two things together in a surprisingly successful partnership.

Style lessons from Oscar Winners

Picture: Rex

The film: Milk, 2008

What it won: Best Actor (Sean Penn)

 

A retro T-shirt is a perennial style winner. Just ask Sean Penn, here playing pioneering politician and gay rights activist Harvey Milk. He wears his with pride in a public parade – you just need to wear yours with pride.

Style lessons from Oscar Winners

Picture: Getty

The lesson: put yourself through the ringer

Slogans make the perfect partner for a close-cut, vintage-looking ringer tee. With echoes of wholesome summer camps via Brooklyn dive bars, it’ll make you look like you’ve just spent a weekend holed up in a cabin in the Catskills, working on your latest album, even if all you’ve been doing is binge-watching Billions in your PJs. 

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