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October 29, 2024 at 11:45am EDT
When it comes to red carpet fashion, the stereotype for men is to just stick them in a traditional tuxedo and off they go. But many actors are now starting to play around with fashion — whether it’s a kilt as a nod to their ancestry or exploring couture clothing. A few stars are leading the way — we see you, Billy Porter.
Related story 53 Times Celeb Women Rocked Their Gorgeous Gray Hair on the Red Carpet
After starring in Pose and having a higher profile, Porter decided to defy fashion norms at the 2019 Oscars, where men tend to dress conservatively. He showed up in a tuxedo gown that stole the show. “My goal is to be a walking piece of political art every time I show up,” he told Vogue. “To challenge expectations. What is masculinity? What does that mean? Women show up every day in pants, but the minute a man wears a dress, the seas part.”
He’s not the only one pushing the envelope because Jared Leto and even Pete Davidson are feeling the freedom and confidence to express themselves through their wardrobe. It’s a reminder that wardrobe doesn’t have to be drawn down gender lines — it’s a work of art that some men are choosing to display with self-assuredness.
See all the men who have worn dress and skirts on the red carpet!
A version of the article was originally posted in May 2022.
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Darren Criss
Image Credit: Kristina Bumphrey/WWD via Getty Images
Darren Criss stepped out of the box at the 2024 CFDA Fashion Awards in this billowing Christian Siriano magenta skirt paired with this opened cropped blazer.
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Eddie Redmayne
Image Credit: Gilbert Flores/Variety via Getty Images
Eddie Redmayne matched with his wife Hannah Bagshawe at the 2024 Met Gala in matching black and white printed dresses by Steve O. Smith. The Oscar winner styled the tulle dress with black socks and matching dress shoes.
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Gustav Magnar Witzøe
Image Credit: Gilbert Flores/Variety via Getty Images
Norwegian billionaire Gustav Magnar Witzøe proved to be one of the biggest risk-takers at the 2024 Met Gala in this custom Versace outfit comprised of a bejeweled bodysuit, a wrap-around cape and a layered flowy skirt. According to designer Amar Faiz, the look was inspired by A Midsummer Night’s Dream by William Shakespeare.
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Jared Leto
Image Credit: Dominique Maitre for WWD
Jared Leto frequently plays with feminine silhouette but still opted to keep his legs warm when he stepped out at a Givenchy fashion show in September 2023 with a skirt styled over pants.
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Billy Porter
Image Credit: Gilbert Flores/Variety via Getty Images
Billy Porter has been dabbling in the dress trend long before it was a trend and always shows of his elaborate, extravagent style like this beautiful gown at the 2023 Golden Globes.
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Brad Pitt
Image Credit: Sebastian Reuter/Getty Images for Sony Pictures
Brad Pitt turned heads when he arrived at the Bullet Train screening in Berlin in this brown skirt that showed off his many leg tattoos. Pitt had a very nonchalant response when asked about why he wore the item.
“I don’t know!” Pitt told Variety. “We’re all going to die, so let’s mess it up.”
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Michael Urie
Image Credit: Jennifer Graylock/PA Images via Getty Images
At the 2019 Met Gala, Ugly Betty alum Michael Urie arrived in a gender-bending look that truly embodied the theme “Camp.”
“Christian Siriano is a genius,” Urie said of the designer of the look in a conversation with Page Six after debuting the look.
“And his staff and he made it so impeccably, that it was comfortable,” he added. “I had a high heel that was the same height as a Doc boot, it was brilliant, and I could pee!”
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Oscar Isaac
Image Credit: Karwai Tang/WireImage via Getty Images
Oscar Isaac looked so handsome in his Thom Browne gray kilt at the premiere of Moon Knight at in London in March 2022.
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Pete Davidson
Image Credit: WireImage
Pete Davidson knew how to make a fashion moment happen with his tailored Thom Browne dress at the 2021 Met Gala.
He later joked about the look in an episode of SNL, saying: “The truth is, I already wear a dress or paint my nails sometimes just because I love making my uncles uncomfortable…”
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Brandon Wilson
Image Credit: Michael Buckner/Variety/Penske Media via Getty Images
Brandon Wilson made heads turn with his khaki kilt at the premiere of The Way Back in 2020.
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Billy Porter
Image Credit: Michael Buckner/Variety via Getty Images
Pose star Billy Porter stunned in a white gown when he was honored with a star on the Hollywood Walk of Fame in 2022.
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Jared Leto
Image Credit: Gilbert Flores for Variety
Jared Leto opted for a leather mini dress and thigh high boots at the 2023 MTV Video Music Awards.
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Jared Leto
Image Credit: Taylor Hill/FilmMagic via Getty Images
Admittedly, Leto’s dress at the 2019 Met Gala was definitely not the most eye-catching part of his look but it turned heads never the less.
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Odell Beckham Jr.
Image Credit: Kevin Mazur/MG19/Getty Images for The Met Museum/Vogue
We love that an NFL star like Odell Beckham Jr. decided to take a fashion risk at the Met Gala in 2019 — that moment paid off
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Billy Porter
Image Credit: Michael Buckner/Variety/Penske Media via Getty Images
Porter looked stunning in a pink, blazer-style dress at the premiere of his directorial project Anything’s Possible in 2022.
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Kyle MacLachlan
Image Credit: PA Images via Getty Images
Honoring his Scottish ancestry, Kyle MacLachlan walked the runaway at a charity fashion show in 2010
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Vin Diesel
Image Credit: Toni Anne Barson/WireImage via Getty Images
We had to go back to 2003 to find this photo, but Vin Diesel showed off his muscular legs at the MTV Europe Awards.
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Image Credit: Sebastian Reuter, Jennifer Graylock/PA Images, Karwai Tang/WireImage via Getty Images, Michael Buckner/Variety
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