13 of the best menswear looks from Oscars history

Oscar Holland, CNN

Audrey Hepburn in Givenchy, Nicole Kidman in Dior, Halle Berry in Elie Saab. History’s great Oscars outfits are iconic, era-defining — and almost exclusively female.

This is hardly surprising. Male attendees have long been expected to abide by a black-tie dress code, and most appeared happy to oblige. Even stars known for outlandish fashion would stick with the go-to tuxedo at this most formal of events.

Yet there have been some glorious exceptions.

With a dash of color, some gentle rule-breaking and a little help from musicians (the Grammys red carpet proves that the music industry is far less concerned with formalities than its silver screen counterpart), some of Hollywood’s more daring men have broken the mold. And with wardrobe etiquette increasingly relaxed in recent years, each ceremony seems to welcome more exceptions to menswear orthodoxy than the last.

Here are 13 of the best men’s looks from Oscars red carpet history:

Pharrell Williams’ camo shorts

Most men are too scared to wear shorts to the office, let alone Hollywood’s most glamorous red carpet. But Pharrell Williams is not most men.

The musician — and now creative director at Louis Vuitton — smashed convention with camouflage-print jacket and shorts. Arriving with wife Helen Lasichanh, he completed the look with a pair of Doc Martins, a diamond necklace bearing his own name and socks as crisp as his shirt.

We could equally have included the Lanvin shorts he wore to the same event five years earlier. But 2019 was the year that Pharrell’s exposed knees made it onto the rarified Oscar stage, as he presented the award for Best Animated Feature Film.

Billy Porter’s tuxedo gown

Velvet jacket? Check. White tuxedo shirt? Check. From the waist up, Billy Porter was a picture of black-tie formality, his ruffled cuffs and exaggerated bow tie the only subtle hints of flamboyancy. From the waist down, however, his Christian Siriano-designed gown was among the most radical fashion statements ever made at the Oscars.

This isn’t to say that genderfluid menswear was especially remarkable by 2019 (look no further than that year’s camp-themed Met Gala). But this was the moment that truly smashed the gender binary on Hollywood’s most strait-laced red carpet.

Isaac Hayes’ fur trim

The fur trims, flared pants and pastel colors of early-1970s menswear rarely found their way onto the era’s Academy Awards’ red carpets. Issaac Hayes was among the welcome exceptions.

Taking the stage to claim Best Original Song, for his theme from “Shaft,” Hayes looked every bit the part in a navy suit with baby blue trim and a matching ruffled shirt and bow tie.

His rendition of the winning song was a different story altogether: He ditched the suit to perform shirtless (and wrapped in gold chains).

Michael Caine’s classic cut

It would be remiss not to include at least one conventional black-tie outfit in this list. And few stars have done it as effortlessly as Michael Caine. The example above is from 1984, the year he was nominated as best actor for his turn in “Educating Rita” (he also presented two awards that night), though we could have chosen almost any Oscars appearance.

As ever, the tailored cut, big butterfly bow tie and wide-rimmed spectacles exemplified why Caine has long been a British style icon.

Spike Lee and Mahershala Ali’s hats

Headwear is a rare sight on the Oscar red carpet. And yet, 2019 gave us two of the best examples at once, as director Spike Lee and actor Mahershala Ali posed together with their awards for “BlacKkKlansman” and “Green Book,” respectively.

Wearing a mandarin-collar shirt under his black jacket, Ali put a formal spin on the beanie in a felt design by milliner Gigi Burris. Lee, meanwhile, paired his purple Ozwald Boateng suit with a matching captain’s hat and a necklace bearing the symbol used by singer Prince, to whom the outfit appeared to pay homage.

Speaking of Prince…

Prince of purple

The “Purple Rain” singer didn’t disappoint in 2005, when he presented the award for Best Song in an immaculate velvet tuxedo jacket — in his signature shade, of course. He completed the look with a pair of floor-length, wide-legged pants that wouldn’t look out of place on 2023’s red carpet.

Although bold by Oscars standards, it was relatively formal compared to the bedazzled hooded cape he’d worn to the ceremony exactly 20 years earlier.

Simu Liu’s red carpet red

A colored tuxedo is a simple but effective way to stand out from the crowd — even if, in the case of actor Simu Liu, the color almost perfectly matches the red carpet itself.

The most recent entry on our list, Liu impressed at last year’s awards in this suave Atelier Versace design. Speaking to Canada’s eTalk on his way into the venue, the “Shang-Chi” star said Donatella Versace had suggested he wear the look shirtless at the after party. “If Donatella Versace tells you to do something, that’s it,” he said. “It’s done.”

Corey Feldman channels Michael Jackson

The 1989 ceremony is considered among the worst Oscars ever — not least because 18 young actors were asked to perform a poorly received musical number, “I Wanna Be an Oscar Winner.” Among them was child star Corey Feldman, who had appeared in “The Goonies” four years earlier.

Whether it was a teenage disregard for dress codes or simply the exuberance of youth, the 17-year-old (pictured here with a 14-year-old Drew Barrymore) tore up the rulebook in a red shirt, embroidered blazer and sunglasses. And if it looks like he’s channeling Michael Jackson, that was probably the point: His on-stage performance featured dance moves inspired by the King of Pop.

Questlove’s golden Crocs

If you have the audacity to wear Crocs to the Oscars — or any red carpet, for that matter — then at least make them golden ones.

With 2021’s ceremony delayed and scaled back amid the Covid-19 pandemic, there were plenty of casual, lockdown-friendly looks on the red carpet that year (see Best Director winner Chloé Zhao’s white sneakers). But it was producer and drummer Questlove, the show’s musical director and in-house DJ, who pulled it off best, matching his comfy footwear with a navy suit, glasses and patterned facemask.

Val Kilmer’s mullet-plus-tux

It was business at the front and party at the back for Val Kilmer, who in 1984 paired a timeless tuxedo jacket with a somewhat more fleeting hairstyle: a mullet.

Is a haircut really an item of menswear? Probably not. Should you wear a white bow tie to a black-tie event? Probably not. But while Kilmer’s then-girlfriend Cher grabbed the limelight on the night she was nominated for her performance in “Silkwood,” her plus-one was, in hindsight, the epitome of boyish ’80s charm.

Robert Downey Jr’s Edwardian chic

In an era when the media started paying attention not only to what you were wearing, but who you were wearing, Robert Downey Jr. turned to fashion designer Richard Tyler for this dandy look in 1993.

Nominated that year for his performance in “Chaplin,” the actor looked dapper in a velvet suit accessorized with what the New York Times described at the time as an “Edwardian foulard.”

Jared Leto’s risk pays off

White jackets are a risk — and not just because of stains (though the Oscars doesn’t actually serve food). But Jared Leto’s 2014 effort, designed by Saint Laurent, hit the mark perfectly.

He wasn’t alone in his decision to wear white that night (see Matthew McConaughey and Ryan Seacrest), but his perfectly fitted jacket was the only one to make it onto best dressed lists. The key to his success? A red bowtie and the glimpse of a pocket square that brought everything together.

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