(CNN) — Audrey Hepburn dressed in Givenchy, Nicole Kidman in Dior, Halle Berry in Elie Saab. The great outfits of Oscar history are iconic, era-defining, and almost exclusively female.

This is not surprising. Male attendees have long been expected to adhere to an etiquette dress code, and most seemed happy to do so. Even stars known for their flamboyance chose tuxedos for this very formal event.

However, there were some glorious exceptions.

With a splash of color, some gentle rule-breaking, and a little help from the musicians (the Grammys red carpet proves the music industry is far less concerned with formalities than its big-screen counterpart), some of the boldest men of Hollywood broke the mold. And with the dress code becoming more flexible in recent years, each ceremony seems to register more exceptions to menswear orthodoxy than the last.

Here are 13 of the best men’s looks in Oscar red carpet history:

Pharrell Williams Camouflage Shorts

(Dan MacMedan/Getty Images)

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

The musician, and now Louis Vuitton’s creative director, broke convention in a camouflage-print jacket and shorts. Arriving with his wife Helen Lasichanh, he completed the look with a pair of Doctor Martins, a diamond necklace with his name on it and a pair of socks as immaculate as his shirt.

We might as well have included the Lanvin shorts he wore to the same event five years earlier. But 2019 was the year Pharrell’s exposed knees arrived on the rarified Oscar stage to present the Best Animated Feature award.

Billy Porter’s tuxedo dress

(Neilson Barnard/Getty Images)

Velvet jacket? checked. White tuxedo shirt? checked. From the waist up, Billy Porter was the very picture of black tie formality, his ruffled cuffs and exaggerated bow tie the only touches of flamboyance. From the waist down, though, her Christian Siriano-designed gown was one of the most radical fashion statements ever made at the Oscars.

That’s not to say that gender-fluid menswear was especially notable in 2019 (look no further than that year’s Met Gala). But this was the moment that truly broke the gender binary on Hollywood’s strictest red carpet.

Isaac Hayes Leather Finishes

(Michael Ochs Archives/Getty Images)

The fur trim, baggy pants, and pastel colors of early ’70s menswear rarely made it to Oscar red carpets at the time. Isaac Hayes was one of the welcome exceptions.

Taking the stage to accept the Best Original Song award for his track “Shaft,” Hayes wore a navy suit with baby blue accents, a ruffled shirt and a matching tie.

His rendition of the winning song was another story: he ditched the suit to perform shirtless (and wrapped in gold chains).

Michael Caine’s Classic Cut

Bob Riha Jr/Getty Images

I would be remiss not to include at least one conventional tuxedo on this list. And few stars have used it as naturally as Michael Caine. The example is from 1984, the year in which he was nominated for best actor for his role in “Educating Rita” (that night he also presented two awards), although we could have chosen almost any of his appearances at the Oscars.

As always, the fitted cut, large bow tie and wide-framed glasses exemplify why Caine has long been an icon of British style.

Spike Lee and Mahershala Ali hats

(Jeff Kravitz/FilmMagic/Getty Images)

Hats are a rare bird on the Oscars 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 her black jacket, Ali put a formal spin on the hat in a felt design by milliner Gigi Burris. Lee, meanwhile, paired his purple Ozwald Boateng suit with a matching captain’s cap and a necklace emblazoned with the symbol of singer Prince, whom he seemed to pay homage to.

Speaking of prince…

prince in purple

Michael Caulfield/WireImage/Getty Images

The “Purple Rain” singer didn’t disappoint in 2005 when he presented the Best Song award in a pristine velvet tuxedo — in his signature hue, of course. She completed the look with baggy floor-length pants that wouldn’t look out of place on the 2023 red carpet.

While edgy by Oscar standards, it was relatively formal compared to the stunning hooded cape she’d worn to the ceremony exactly 20 years earlier.

Simu Liu’s Red Carpet Red

(Stephen Lovekin/Shutterstock)

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

Liu, the latest addition to our list, wowed at last year’s awards with this elegant Atelier Versace design. Speaking to eTalk from Canada, the “Shang-Chi” star said Donatella Versace suggested she wear the shirtless look to the after party. “If Donatella Versace tells you to do something, that’s it,” she said. “If it does”.

Corey FeldmanMichael Jackson

(Steve Granitz/WireImage/Getty Images)

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

It was because of the adolescent scorn that we showed because of the dress codes or simply because of the exuberance of youth, the 17-year-old (in the photo with a 14-year-old Drew Barrymore) broke the rules with a red shirt, an embroidered blazer and sunglasses. And if he looks like he’s imitating Michael Jackson, that’s probably why: his stage performance featured dance moves inspired by the King of Pop.

Questlove Gold Crocs

(Matt Petit/AMPAS/Getty Images)

If you have the audacity to wear Crocs to the Oscars, or any red carpet, at least they’re gold.

The 2021 ceremony was postponed and also scaled back amid the Covid-19 pandemic, so there were plenty of casual, friendly looks on that year’s red carpet (see Best Director award winner Chloé Zhao’s white sneakers). .

But it was producer and drummer Questlove, who is also the program’s music director and DJ, who dressed the best, combining his comfortable shoes with a navy blue suit, glasses and a printed mask.

Val Kilmer’s most mullet tuxedo

(Bill Nation/Sygma/Getty Images)

In 1984, Val Kilmer paired a timeless tuxedo jacket with a slightly more ephemeral hairstyle: a mullet.

Is the haircut a man’s garment? Probably not. Should I wear a white tie to a black-tie event? Probably not. But while Kilmer’s then-girlfriend Cher stole the spotlight the night she was nominated for her performance in “Silkwood,” her date was, in retrospect, the epitome of ’80s girlish charm.

The Edwardian elegance of Robert Downey Jr.

(Steven D. Starr/Corbis/Getty Images)

At a time when the media began to pay attention not only to what was being used, but who was using it, Robert Downey Jr. sought out stylist Richard Tyler for this sleek look in 1993.

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

Jared Leto’s Risk Was Worth It

(Christopher Polk/Getty Images)

White jackets are a risk, and not just because of the stains (though no food is served at the Oscars). But Jared Leto’s 2014, designed by Saint Laurent, nailed it.

He wasn’t the only one who decided to wear white that night (see Matthew McConaughey and Ryan Seacrest), but his perfectly fitted jacket was the only one to make best-dressed lists. The key to your success? A red bow and the glimmer of a pocket handkerchief that tied it all together.