Fashion

The 25 Most Stylish Men to Ever Step Foot on the Oscars Red Carpet

From Hollywood icons to legends in the making, here are the Academy Awards' best-dressed attendees of all time.
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When it comes to celebrity style, you can't do better than the Oscars. Ever since its founding in 1929, the Academy Awards has been the premier spot for stars to flex their formalwear skills for all the world to see. So, with the 2019 installment on the way, we decided to take a look back at the ceremony's long history of impeccably dressed guys. From Bogie in classic black-tie to younger actors like Michael B. Jordan bringing old-school sophistication into the modern age, here, in alphabetical order, are the 25 best-dressed men to ever hit the Oscars red carpet. 

Humphrey Bogart

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

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Chadwick Boseman 

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

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Marlon Brando 

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

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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. 

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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. 

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George Clooney 

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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. 

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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. 

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Clint Eastwood 

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

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Ryan Gosling 

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

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Cary Grant 

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

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Samuel L. Jackson

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

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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. 

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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. 

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Steve McQueen 

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

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Paul Newman 

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

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Jack Nicholson 

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

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Dev Patel 

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

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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. 

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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. 

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Prince 

He's Prince. Enough said. 

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Robert Redford 

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

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Frank Sinatra 

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

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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. 

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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.

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This story originally appeared on Esquire.com. Minor edits have been made by the Esquiremag.ph editors.

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