The Best Dressed Men at the Oscars (who aren’t Brad Pitt, George Clooney or Leonardo Dicaprio)

And the nominees for Least Original Oscars-Related Blog Post are . . .

The Most Stylish Men To Ever Set Foot On The Oscars Red Carpet,’ Esquire

Oscars 2020: The Best Dressed Men Of All Time,’ The Independent (UK)

34 Of The Best Dressed Men To Walk The Red Carpet,’ The National (UAE)

The Oscars: The Best Dressed Men Of All Time,’ GQ

I honestly thought this subject would not have been covered to the extent it has, especially in advance of the 92nd Academy Awards, which take place tonight in Hollywood.

Tomorrow will offer a buffet of post-Oscars discussion about gowns, but it says something about the increasing attention to men’s fashion that there are so many variations on this particular theme in the media.

The problem is, I looked at all these stories, and so many of them felt the same. The choices are either super-retro (Marlon Brando, Humphrey Bogart) kind of daffy (the Jared Leto and Pharrell Williams getups) or just inimitable (basically anything Spike Lee chooses to wear).

I also wonder if sometimes the decisions in these stories is based on the fact that many of the men featured are winners, which might somehow skew our sense of how good they look.

The reality is that most, if not all, of the usual suspects in the Oscars best-dressed men pantheon had their looks created by stylists. They are not, by nature, necessarily that stylish.

The reason I think the Oscars matter, however, is that it probably represents the single most visible night in which men don formalwear. The Academy Awards celebrate the making of fictional worlds, but the Oscar red carpet offers a common touchstone on how to dress in real life.

I decided to do a little digging — actually, a lot of digging — in the Academy Awards press gallery archives to see what I could learn that would be useful, rather than merely historic.

What follows is mostly from the last few years, because I found that the Academy’s photo archives confine the men mostly to crowd shots until about 2015. I also wanted to focus on what’s modern and relevant.

Most of these guys have never walked home with a little gold man, but they’ve offered some golden style moments worth remembering the next time you ever have to really turn it out for a wedding, a charity event or anything similar:

Aaron Poole / ©A.M.P.A.S.

Henry Cavill, 2016

Look carefully and you’ll see this jacket is a thick, rich velvet that, along with the shawl collar, allows him to own the room in the most relaxed way possible. Superman would never want to put on tights again.

Michael Baker / A.M.P.A.S.


It helps to be skinny when you’re opting for a double-breasted jacket, but there’s no question it reinforces the idea of a tuxedo (or even a suit) as a kind of armour in wrapping that extra layer around your torso. I really like how the buttons on this one are a little oversize, hinting that this is meant to be worn on a big night.

Sara Wood / ©A.M.P.A.S.

The Weeknd, 2016

Living proof that you can be on the stocky side and still pull of a tuxedo without looking like a penguin. Notice how thin his lapels are, and how the cut of the jacket doesn’t try to be form-fitting but looks effortlessly comfortable.

Mike Baker / ©A.M.P.A.S.

Jharrel Jerome, 2017

The white jacket can be hard to pull off, but I think this works because the formality of the black shirt and tie make it seem a little less stiff and showy. Instead, he just looks like he’s having the best time, which is what any tuxedo or formalwear look should do.

Richard Harbaugh / ©A.M.P.A.S.

Javier Bardem, 2018

The risk you take with a completely monochromic look is that you might seem like you’re trying to make yourself invisible, or that, in trying to make your fashion unnoticeable, it becomes more so. There’s a discreet pattern in this jacket, though, that rewards you for taking a closer look. BTW, this guy seems to show up almost every year and looks unfailingly great each time.

Richard Harbaugh / ©A.M.P.A.S.

Henry Golding, 2019

Vests with a tuxedo have almost become as passe as the cummerbund — there’s a fear you’ll be mistaken for a Downton Abbey footman — but I think there’s something about this look that shows you’re taking the event seriously enough to show respect by wearing something that doesn’t just look good, but feels almost ceremonial. (Plus, no one wearing a watch like that would be serving food on a tray.)

Mike Baker / ©A.M.P.A.S.

David Oyelowo, 2017

As bold as you want to get for a big night, and wouldn’t work if the tie weren’t black. It’s a good example of what you could think about if you were not just attending a formal event, but helping lead it in some way, either as MC or as a guest speaker of some kind. Yes, it will draw attention, but only in the right way because it’s perfectly balanced and remains elegant, rather than aggressive in its creativity.

If you’re watching the 2020 Oscars this year, or just looking back at it afterwards, don’t just focus on who’s giving the acceptance speeches. Keep an eye out for the guys who look like they’re ready to step up to the podium at any time.

Feature image: Detail from a photograph of actor Glen Powell, 2018. Mike Baker / ©A.M.P.A.S

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