Men Wearing Skirts Dresses in Red Carpet Photos: Brad Pitt and More

Kristyn Burtt

May 8, 2024 at 12:09 AM·4 min read

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.

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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Eddie Redmayne

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.

Gustav Magnar Witz?e

Gustav Magnar Witzøe — Gustav Magnar Witz?e

Norwegian billionaire Gustav Magnar Witz?e 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.

Jared Leto

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.

Billy Porter

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.

Brad Pitt

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.”

Michael Urie

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!”

Oscar Isaac

Oscar Isaac looked so handsome in his Thom Browne gray kilt at the premiere of Moon Knight at in London in March 2022.

Pete Davidson

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…”