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The 15 Most Stylish Characters in Oscar Winning History

The 15 Most Stylish Characters in Oscar Winning History

The 15 Most Stylish Characters in Oscar Winning History

It's Oscar time and where most magazines will spend their pre-event coverage discussing red carpet style, we present what's really cool about the sartorial silver screen.

Behold, the most stylish movie characters in Academy Award-winning history...

(Images: Rex/YouTube)

Argo (Best Picture, 2013)

If they gave out Oscars for best beards (and they should!) then, two years ago, Ben Affleck would have gone home with Best Beard, Best Beard in a Leading Role and Best Short Beard, no doubt about it. And look at his face, he knows it too.

Tell you who wouldn't have won Best Beard at the Oscars, though. This guy. Next!

No Country For Old Men (Best Picture, 2008)

Everything we said about Affleck's beard previously also applies to Brolin's triumphant Selleck-esque 'stache in No Country. But more than just that, this movie single-handedly made binoculars cool once more.

The shirt pictured will never go out of fashion, but you may struggle to pull off the hat down the Old Dog & Duck. Best leave the rifle at home, too. 

The Artist (Best Picture, 2012)

Ready for a brace of costume facts? The Artist was the first black and white film to win the Best Costume Oscar since the discontinuance of the Best Costume (black and white) Oscar in 1967. The last black and white film to win a Costume Oscar, for Best Costume (black and white), was Who's Afraid of Virginia Woolf? forty-five years earlier. Everybody get that? Us neither. But by God Dujardin looked cool. 

The Deer Hunter (Best Director, 1978)

The tormented Vietnam PoW look is not one to be rocking right now (next year it'll be huge, honest) but craggy mountain winter wear is still a big deal. Don't take our word for it - our in-house Style Director handpicked some choice wardrobe items based entirely on De Niro's outdoor adventurer look. Check it out

On The Waterfront (Best Actor, 1954)

Ever stand by the shore in the bracing wind and not think about this movie? Us neither. Chunky knits, cosy coats and robust jeans; face facts, without On The Waterfront's style lessons winter would be a season of human hibernation. As it stands, though, it provides some of our coolest urban catwalks. 

Million Dollar Baby (Best Picture, 2005)

The bad news is there's only one man on Earth who can pull off a retro 80s tracksuit top paired with a fedora, and it's not you. 


The Color Of Money (Best Actor, 1986)

The greatest sunglasses in movie history, a top five:

5. Al Pacino, Scarface

4. Cary Grant, North By Northwest

3. Robert De Niro, Taxi Driver

2. Steve McQueen, The Thomas Crown Affair 

1. Paul Newman, The Color Of Money


The Godfather Part II (Best Picture, 1975)

Michael's two-piece, lightweight, grey dupioni silk suit is not just the best outfit in this insanely stylish film, it's arguably the coolest suit ever worn on celluloid. It's a three buttoned suit jacket with three buttons on each cuff and a straight flapped hip pocket on each side. The white shirt and silk, black tie were worn with a black leather belt with a rounded silver clasp and (although not seen on camera), light grey, tasseled loafers. So now you know. 

The Sting (Best Picture, 1974)

Guess which two dudes were making white vests cool when Bruce Willis was still a teenager. Go on, guess. Bonus points for wearing braces, Paul. 

Training Day (Best Actor, 2001)

Another one from the "You'll look stupid if you try to mimic his wardrobe, but he's still incredibly cool" category. Denzel Washington has frequently said that Detective Alonzo Harris is his favourite character that he's ever played and little surprise - Alonzo oozes style. And corruption.

Mainly corruption. 

The French Connection (Best Picture, 1972)

The pork pie hat enjoyed a crazy resurgence after Hackman appeared wearing the headwear of choice of Eddie Egan, the real life cop on which Popeye Doyle was based. So in love was Egan with his pork pie he refused to lend it to Hackman to shoot the movie with, so they had to source him one from elsewhere. Fair enough, really. 

One Flew Over The Cuckoo's Nest (Best Picture, 1976)

Imagine being handed a set of patient overalls and somehow making them look good. One of many talents McMurphy (Jack Nicholson) had that most of us can only dream of. Another one of those qualities was feigning brain damage just minutes after undergoing electroconvulsive therapy. Don't really want to be in a position where we're able to do that, truth be known. 

Ray (Best Actor, 2004)

It's pretty simple really: If Ray Charles pioneered soul music and Jamie Foxx got Ray Charles's character to a tee, then Ray gets into our most stylish Oscar winners list. 

Interesting aside: Ray Charles only wore sunglasses made by designer Billy Stickles. 

Annoying aside: You'll struggle to get hold of any these days. 

To Kill A Mockingbird (Best Actor, 1963)

Towering 6 ft 3 and impeccably turned out in his immaculate three-piece, Gregory Peck's Atticus Finch was a movie hero unlike any before, or after. No brawn, no side arm, just pitch perfect life pointers in, seemingly, every line of dialogue. Glasses were rockin' too.

There Will Be Blood (Best Actor, 2007)

The annoying truth is that Daniel Plainview's son, HW, rocks a suit better than most of us, but it's Daniel who leaves us awestruck with his sartorial acumen. Costume designer, Mark Bridges, gave Daniel Day Lewis three hats to choose from and the actor spent time with them all before deciding on his preference. Day Lewis took them home and lived with them for days before settling on this one [pictured] as the one he felt most comfortable with. And by the way, the sweat stains on the hat are real.