STYLE. GROOMING. INSPIRATION. ADVICE.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.