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FEATURE

STYLE LESSONS FROM OSCAR WINNERS

By Sarah Lillywhite, February 24, 2019

It’s Oscars time again, and while the likes of Black Panther, Bohemian Rhapsody and Green Book square up against each other for Best Picture, and Christian Bale, Rami Malek and Bradley Cooper fight it out to see who’s 2019’s top dog, we’re delving into the archives to find the most stylish takeaways from past Academy favorites. 
Armie Hammer and Timothee Chalomet in Call Me by Your Name

Picture: Rex Features

The film: Call Me By Your Name, 2017

What it won: Best Adapted Screenplay

 

This sunsoaked tale of clandestine meetings, first loves and shady dealings with peaches is rightly proud of its '80s gear. Baggy, short-sleeved shirts, chino shorts, cut-offs and polos abound as Armie Hammer and Timothée Chalomet romp around the Italian countryside. It's the style blueprint for all our future summer vacays. 

Man in Milan wearing shorts

Picture: IMAX TREE

The lesson: fall in love with the '80s 

 

This guy has very much taken the summer throwback vibe to heart. The shorts are practically the swimming trunks Hammer wears for half the film; the shirt could be one of Chalomet's date-night ones; the tennis-vibes sneakers and ankle socks were made for scuffing up in the Lombardy soil. Just substitute the clutch bag for a battered old novel and he could be an extra. 

Al Pacino in The Godfather

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.

Man wearing a cravat

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 color. Bellissimo.

Dustin Hoffman in The Graduate

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 cord blazer our geography teachers wore could look cool, we’d have eaten our beanies. 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. 

Man in cord jacket and jeans

Picture: IMAX TREE

The lesson: here’s to you, normcore staples

 

Replace his polo shirt with an Fair Isle knit, and his clean-shaven look with an impressive beard, and you’ve got this guy’s woodsman-meets-dadcore get-up. In summer, just switch up the sweater and boots for a white tee and running sneakers, and it's a fail-safe year-round look. 

Diane keaton and Woody Allen in Annie Hall

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

A man wearing wide leg pants

Picture: Getty

The lesson: wide-leg pants always win

 

This guy knows the enduring power of pale, wide-leg pants 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 turtleneck and charcoal coat, it’s just the right side of Manhattan beatnik. 

Jamie Foxx as Ray Charles

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 have long been in love. 

Man wearing denim tuxedo

Picture: Getty

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

 

It’s not confined to formalwear, either — the tux-style detail peps up streetwear and jersey too. 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.

Sean Penn as Harvey Milk

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.

Man with long hair wearing ringer tee

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 Sex Education's retro summer-camp vibe, it’ll make you look like you’ve just spent a weekend holed up in a cabin in the Catskills, getting up to all sorts of japes, even if all you’ve been doing is watching True Detective in your PJs. 

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