At the end of last year Glamour published a listicle of the “41 Most Memorable Red Carpet Looks” from the past decade. The list featured the usual suspects (Lady Gaga’s hiding-in-a-gone-off-hard-boiled-egg look at the Grammys; Angelina Jolie and the Leg That Went Viral), but only three men (Timothée Chalamet, Billy Porter and Ezra Miller). It was a strikingly low number, but maybe not surprising. For decades, menswear’s slow adaptiveness on the red carpet has felt positively glacial next to women’s. The dress code for celebrity men had long become an exact science. Specifically: everyone dress exactly the same, like they do in the Village of the Damned and at the checkout in M&S.

Obviously, there have been significant exceptions to the black-tie rule, like Robert Downey Jr experimenting with an Ascot tie and a cummerbund or Kiefer Sutherland presciently approximating a noughties hipster in the 80s, or the cast of Interview with the Vampire (Cruise, Pitt, Banderas, Slater) in 1994 looking like the awkward AGM of Hairdressers of Hollywood.

But satirical fashion website Go Fug Yourself’s Heather Cocks thinks these were neon anomalies in a sea of black. “Every era has its pioneers,” she says. “We had dudes in the 80s aping the hair [metal] bands, for example. And Seattle grunge rockers certainly made an imprint in the 90s. And Ashton Kutcher was a big proponent of the trucker hat and Ed Hardy in the 2000s. But those seemed less about fashion than style, and about an idea of coolness that hinged on looking like you didn’t care.”

Get the look: Donald Glover at the 2019 LACMA Gala, Los Angeles. Photograph: Frazer Harrison/Getty Images

This attitude – the “Oh this old thing?” mentality – still exists today. Justin Theroux, one of the world’s most self-consciously stylish actors, told WWD earlier this year: “Fashion doesn’t play that big of a role in my life.” (Cue collective eye roll). It has translated to a controlled, uniform mode of dress at award shows that writer Paul Flynn describes as “a succession of sensationally handsome men looking like fantasy bridegrooms.”

The blah dress code was also related to castability. “In the past, red carpets remained fairly conservative in their dress because showing anything other than the archetypal version of masculinity in any part of your life was deemed as hurting your chances as a leading man,” stylist Joseph Kocharian (Nick Jonas, Liam Payne) explains.

But a real-world reckoning against all forms of toxic masculinity and a generational questioning of what it means to be a man has had a knock-on effect.

“There have certainly always been stylish men on the red carpet,” says Jessica Morgan, the other half of Go Fug Yourself. “There’s a long history of creative male dressers. But I do think that, over the past five to 10 years, we’ve seen more mainstream movie stars, at least, breaking out of the classic blue suit/black tux rut.”

Two heads are better than one: Jared Leto at the 2019 Met Gala. Photograph: Kevin Mazur/Getty Images

This sideways hustle away from the tux cul-de-sac began with wider lapels, flowers in lapels, suit trousers that didn’t match the jackets. In the last couple of award show seasons these small changes have blossomed into outer cummerbunds, capes, chunky high heels and shoulder-hanging chest harnesses. The envelope-pushing seems to work on a scale. On the one side, you have the Jeff Goldblum-types: peacocks like Darren Criss, Donald Glover and Rami Malek who make subtle yet standout statements. In the middle, Michael B Jordan and Timothée Chalamet, as outré and experimental with their red carpet choices as they have been with film choices. And on the other end of fabulosity there are the likes of Ezra Miller and Jonathan Van Ness, for whom every red carpet is a Met Gala red carpet.

Men’s red carpet dressing has never been more filled with potential OMG moments, which highlights a more serious conversation going on about authenticity and truth. Sam Smith’s announcement that they were “genderqueer” was proceeded by the singer’s first red carpet appearance in heels. “There was a time where I’d never ever be able to be myself like this in front of the industry or anyone,” they wrote on Instagram.

Ness to impress: Jonathan Van Ness at the 2019 Creative Arts Emmy Awards, Los Angeles. Photograph: Paul Archuleta/FilmMagic

More recently, Smith made the link between clothing and perception. “I felt like I was playing this ‘Sam Smith’ character that I created. I was depressed because I was this person in suits who other people wanted me to be,” they told Out magazine. “I can wear a suit now, actually, and can feel completely different in the suit, but at the time I felt, I’ve got to be butch for other people.”

Kocharian thinks that a fluidity around the gender conversation has had a knock-on effect on the celebrity world. “There is a more evolved view of masculinity in the past few years where men are able to embrace their femininity, too,” he says. “It is to be celebrated, not suppressed, which in turn has lead to much more creativity and diversity in what we’re seeing on the red carpet.”

Ashley Weston, the stylist who put Chadwick Boseman in a harness, told GQ: “We’re getting into the period of time where no one’s [thinking], ‘OK, is this too feminine? Do we need it more masculine?’” Male actors, she said, aren’t thinking: “‘I still need to look like this because I’m a leading man.’ That’s out of the question now. It’s almost like everyone is looking at things with more neutral goggles.”

Film critic Guy Lodge believes that now actors use their style as something that can supplement their brand. “Male actors dress in ways that support and complement their screen personae,” he says. “Chadwick Boseman has crafted a kind of Afro-futurist red-carpet look befitting of Black Panther. Timothée Chalamet makes offbeat choices that stress his youth and artsiness. Donald Glover has a whole soul-dandy thing going on, and so on. Red-carpet wear has become more of a personality outlet for performers than it used to be.”

Wears it well: Billy Porter at the Like a Boss world premier, January 2020. Photograph: Cindy Ord/FilmMagic

It has coincided with a time when designers such as Gucci’s Alessandro Michele are upending traditional notions of masculine dress. By garnishing A$AP Rocky with a Dot Cotton-esque headscarf, Bad Bunny in a florid nudie suit, or putting Jared Leto in a bejewelled gown (accessorised with a replica bust of his own head – the Met Gala), Michele has changed the conversation. It’s less about binaries and more about a plurality of dressing.

“It’s nice to play with codes. I think that the era of being masculine only if you have a specific suit – it’s over,” he told US GQ’s New Masculinity issue in October. Put simply: the Male Diva rules the red carpet roost. The MD’s best friend is his stylist, he’s a trend starter (that could mean wearing an up-and-coming designer, but that could also mean sporting an unexpected “lewk”) and he will, of course, be trending by the time you read this.

Indeed, he wants to “go viral”, but ultimately with a message. The power of a red-carpet “moment” can have more cultural legacy than the film the actor is promoting and can stay in the public’s mind for a long time after (Jennifer Lopez’ safari Versace dress comes to mind here). And for many that was Billy Porter’s appearance at the 2019 Oscars dressed in a voluminous tuxedo dress. A political, social message wrapped in a red carpet outfit, it was men’s fashion’s big coming out moment. A statement of intent that was impossible to deny. It was the male equivalent of Cher in a glittering Bob Mackie reveal at the 1988 Oscars, 30 years earlier. “It was the arrival of gender-blurring fashion on the red carpet in this really massive, explosive, very mainstream way,” said Washington Post’s Robin Givhan. “He didn’t look like a man who’d earned a seat at that table. He was the table,” Flynn says. “We didn’t know what would happen, but we knew it was a conversation we needed to have,” says Porter’s stylist Sam Ratelle. “Fashion tells the tale of our times, and for Billy, wearing a big ballgown in that space, as a theatre person, as an LGBT person, as a black person, was important.”

For Ratelle the red carpet is like a stage. “It’s a theatre, it’s about having fun,” he says. “Clothes are costumes.”

Suited and booted: Darren Criss at the 2019 Met Gala. Photograph: Jamie McCarthy/Getty Images

But it’s deeper than that. “People have contacted me to say, ‘because of you, I wore a ballgown to my prom’, or ‘because of you I feel comfortable wearing nails or makeup.’”

Ezra Miller is another actor who has utterly invigorated the red carpet. He wore a “bizarre padded gown” (the Sun) to the US premiere of Fantastic Beasts: The Crimes of Grindelwald (actually a piece by Moncler x Pierpaolo Piccioli) and black lipstick. At the London premiere he wore a piece of feather-filled Givenchy couture that resembled a big white bird, and he cosplayed Toadette from Mario Kart at Comic-Con. Because… why not? “He basically sees the fashion industry at large as his dressing up box,” says Teo van den Broeke, GQ’s style and grooming director. “He’s an extraordinary example of a reconstructed man with no concern (and every concern) about the way he is perceived by the wider world. I wish I was brave enough to dress the way he does.” (Guy Lodge adds a note of caution here: “It might still limit his casting prospects a bit if he’s just seen as a beautiful fashion freak,” he says).

‘There was a time where I’d never ever be able to be myself like this’: Sam Smith. Photograph: Javier Bragado/Getty Images

Miller, Porter, Chalamet and their like have opened the door. But what’s the next step? Fashion vlogger Luke Meagher, aka Haute Le Mode, name checks a host of millennial stars who push the envelope with the ease of a generation not burdened by gender preconceptions. When asked who is stepping up, he says: “Lil Nas X definitely, I mean that Prince dedication look by Christian Cowan was superb. Cody Fern has also caught my attention whenever he steps on to a carpet. Mitch Grassi, while we don’t see him on a red carpet as much, shows up and shows out as well, especially in Balenciaga.”

Most tellingly one of his picks is dissolving the gender boundaries completely. “I have to say Rickey Thompson in a Givenchy Fall 2019 look at the People’s Choice Awards was truly the best thing I’ve seen on a man in a while,” he says. “And the best part? That it was a women’s look.”

• This article was amended on 6 February 2020 to change the pronouns which refer to Sam Smith to “they” rather than “he”.