Publication date November 2, 2023

Breaking Gender Barriers: Men in Dresses in Pop Culture

Despite living in the 21st century, many people still have trouble accepting men in dresses.

Western fashion has dictated for centuries that suits are for men and dresses and skirts are for women, and many people have been raised to believe this.

Harry Styles in dress

Source: People

However, male pop culture celebrities such as Gerard Butler, Billy Porter, Harry Styles, and Marc Jacobs have challenged these traditional gender norms by courageously and confidently wearing skirts and dresses.

And to the surprise of many, men have been wearing dresses for centuries.

There is literally no reason why men shouldn't be able to wear skirts and dresses. In fact, they often look absolutely stunning on men.

So as the world moves towards equality, many celebrities are channeling genderless fashion through their dressing style.

Let’s have a look at the 8 male celebrities who are busting gender barriers in fashion and have become guiding lights to the future.

Billy Porter

Billy Porter takes every award show appearance as an opportunity to express himself and make others feel brave enough to follow their heart. 
“I’m a man in a dress, and if I feel like wearing a dress, I’m going to wear one,” says Porter in an interview.  

“My goal is to be a walking piece of political art every time I show up. To challenge expectations. What is masculinity? What does that mean?” He said in another interview.

Porter’s words clearly mark removing the line when it comes to men in dresses and gender barriers. After wearing a tuxedo gown to the 2019 Oscars, he has certainly replaced convention with reinvention.

Harry Styles

Harry Styles Vogue

Source: Vogue

On November 13, 2020, Vogue released its Magazine’s front cover featuring solo artist Harry Styles wearing a blue customized Gucci gown and a Gucci-tailored tuxedo jacket.

While most people fell in love with the photos that were released inside the magazine of him appearing very feminine, some spoke out against it.

In an interview with The Face, Harry Styles said, “What’s feminine and what’s masculine, what men are wearing and what women are wearing—it’s like there are no lines anymore,” and his words say it all.

Harry Styles has clearly become an advocate for the genderless style movement, with dresses, make-up, and jewelry part of his look at several events.

Brad Pitt

Brad Pitt in a matching skirt and blazer

Source: ELLE

Brad Pitt made waves in pop culture by appearing in a matching skirt and blazer on the red carpet for his film "Bullet Train" premiere.

At 58 years old, Brad instead of wearing a three-piece suit dared to opt for a brown linen jacket and skirt with a pink unbuttoned shirt.

To accessorize his ultra-cool outfit, the actor went for a pair of biker boots to show off his shin tattoos, and brown sunglasses to top off the look.

By making this genderfluid fashion statement that has already been validated by many male celebrities, he is helping push opinions forward when it comes to men in dresses. 

Gerard Butler

Gerard Butler wearing kilts

Source: Pinterest

Men in skirts and dresses are often perceived differently by society, but Gerard Butler has proven that they can be cool and stunning too.

He is Scottish, so he says he is used to wearing kilts. But he doesn't like to wear them very often.

Butler says that wearing a kilt has some rules, and he once flashed people at his sister's wedding because of them. Looking good can be hard!

Vin Diesel

Vin Diesel  at MTV Europe Music Awards

Source: IWMBuzz

Vin Diesel, The Fast and Furious star, even knows how to work a skirt. In 2003, at the MTV Europe Music Awards, the muscular actor was spotted wearing a leather skirt.

It clearly shows that he is confident enough in his masculinity that he has no issue wearing a cool leather skirt to an award show.

Also, it appears that he was being respectful because the event took place in Scotland, but it’s more likely he enjoyed his look the most that night.

Marc Jacobs

Marc Jacobs in skirts and dresses

Source: HubPages

Marc Jacobs, a famous designer does not shy away from earring skirts and dresses and even made them a staple in his wardrobe.

A clear defining moment was when he showed up in a pink dress at his Louis Vuitton exhibition in 2012.

It speaks a lot, it gives people inspiration that when we choose to express ourselves on a large stage, just like Marc Jacobs has, we can change the way the world thinks.

As Jacobs states: “I discovered how nice skirts felt to wear. They’re comfortable, and wearing them makes me happy, so I bought more. And now I just can’t stop wearing them.”

“I really do believe that art changes the landscape of the world,” He added. Fashion is an art, so Jacobs is entirely correct. 

Kid Cudi

Kid Cudi in wedding dress

Source: Vogue

Arriving at the event, the rapper star stepped out in a custom bridal gown by ERL, the white-hot West Coast label launched in 2018 by American Emerging Designer of the Year nominee Eli Russell Linnetz.

Kid Cudi said in an interview, “People are going to wonder why you’re trying to be different; it’s just a natural instinct. If I were to walk down the street in a kilt, then dudes would wonder why I was doing that, they’d think I was different or gay.”

“It’s natural for people to point fingers. That’s my whole reason for trying to switch things up; don’t judge a book by its cover,” He added.

Kid Cudi's words and actions have become a catalyst for change. It only takes the effort of a few people to start a trend that will redefine the history of men in dresses. 

Brandon Wilson

Brandon Wilson in a skirt

Source: Out Magazine

Despite the fact that Brandon Wilson is just starting his career in Hollywood, he’s already normalizing men in dresses. He showed up in a skirt to the premiere of his movie “The Way Back”, starring Ben Affleck.

What made his choice even cooler and appreciable is that the movie is about basketball and Brandon wasn’t afraid to sprinkle in some femininity along with his on-screen sporty persona.

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