The Most Stylish Men to Ever Step Foot on the Oscars Red Carpet

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On February 9, the Dolby Theater in Hollywood, California, will play host to the 92nd annual Academy Awards. All (well, most) of the biggest celebrities either in or orbiting the movie world will be there. Tuxes will be worn. Gowns will be donned. And at the end of the evening, once the little gold men are all handed out, that’ll be another Oscars in the books, with nothing left but the memories of who won, who got robbed—and who got a fit off. To help put this year’s edition in context, we’ve taken a look back at the last 90-plus years of Academy Awards style and rounded up the very best, from Brando and McQueen to Boseman and Momoa. Here, in alphabetical order, are the best-dressed guys to ever take a stroll down the Oscars red carpet.

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Mahershala Ali

The hat. The glasses. The impeccable brocade dinner jacket from Ermenegildo Zegna XXX. It all comes together to create an incredibly stylish red-carpet look (one we even declared his best yet).

Humphrey Bogart

The man was basically the personification of the Golden Age of Hollywood.

Chadwick Boseman

A relative newcomer, Boseman knows exactly how to make the red carpet feel exciting without losing sight of just plain looking great.

Marlon Brando

At his peak, he was a force to be reckoned with.

Jeff Bridges

When you talk about the power of grooming on the red carpet—and its ability to set you apart from the pack—you’re talking about Bridges.

Michael Caine

He’s looked great in more recent Oscars appearances, too. But Caine’s thick-framed heyday will live forever as a high-water mark of British style.

George Clooney

Whether bearded and coiffed or clipped and clean-shaven, Clooney brings classic vibes to the modern red carpet in just the right way.

Sammy Davis Jr.

Just look at those shaves. And that collar. And that jewelry. The man was one of a kind.

Daniel Day-Lewis

As much of a chameleon on the carpet as in his films, every iteration of Daniel Day-Lewis’s award-show style is impressive.

Clint Eastwood

The tux is good. The hair and beard are even better.

Ryan Gosling

The man can make a ruffle-front shirt look not just acceptable but downright enviable. That’s nothing to scoff at.

Cary Grant

Considering Grant quite literally built himself in the of collected elegance, it should come as no surprise that he looks fantastic in formalwear.

Samuel L. Jackson

Those. Shades. Samuel L. has been cool for longer than some red-carpet newcomers have been alive.

Michael B. Jordan

Michael B. Jordan knows that blending classic (the tux) with a touch of modernity (the fit, the shoes) is always a good move.

John Legend

Aside from the fact that he always looks perfectly pulled-together, he seems like he’s having such a good time. Style is about more than just clothes, and Legend is proof.

Steve McQueen

The King of Cool also knew a thing or two about getting dressed up.

Jason Momoa

A pink velvet Fendi tux—paying homage to Karl Lagerfeld, who passed away shortly before the 2019 Oscars—is a flex. Adding a pink velvet Fendi scrunchie to match? That’s truly impressive.

Paul Newman

Don’t smoke. But if you want to mimic literally everything else about Newman in this photo, go for it.

Jack Nicholson

Yes, he’s wearing sunglasses indoors and at night. No, I don’t have a problem with that.

Dev Patel

Wearing a white dinner jacket and not looking a little try-hard is a tough move, but Patel pulls it off perfectly.

Gregory Peck

Proof that the old-school penguin suit—perfectly tailored, of course; just look at that sliver of cuff—is as timeless as they come. As is Peck.

Sidney Poitier

A masterful dresser in all regards—his casual outfits are so damn cool it hurts—Poitier never failed to deliver sophistication on the red carpet.

Billy Porter

If there’s one look that defined the sense of boldness and openness that flourished at the end of the 2010s, this is it. Bonus: It sets the stage for a very interesting new decade.

Prince

He’s Prince. Enough said.

Robert Redford

There was, it seems after careful photo research, no point at which Robert Redford was not cool.

Frank Sinatra

Ol’ Blue Eyes wore a tux like it was his job. And he was very, very good at that job.

Denzel Washington

Sure, there were a few ’90s missteps along the way (this is, by the way, true for everyone who went to the Oscars between 1989 and 200). But when Denzel delivers, he delivers.

Pharrell Williams

Ever the red-carpet rebel, you get the sense that Pharrell knows every rule in the book—which is why he can break them and still look this good.

Jonathan Evans is the style director of Esquire, covering all things fashion, grooming, accessories, and, of course, sneakers.

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Source : Esquire