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FEATURE

OSCAR WINNERS' STYLE LESSONS

By Sarah Kershaw, February 24, 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 favorites. 
Style lessons from Oscar Winners

Picture: Rex

The film: Annie Hall, 1977

What it won: Best Picture

 

Arguably everyone’s favorite 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: 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: 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 film. 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: 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: 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 pants — a micro-trend with which menswear’s highest echelons are currently in love. 

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.

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