14 Celebrity Men Who’ve Worn Skirts and Dresses and Looked Fabulous in Them

Even though it’s the 21st century, society seems to still have trouble accepting men who wear feminine clothing. But skirts and dresses on men often look absolutely stunning, so there’s literally no reason for these fashion items to be worn exclusively by women.

1. Vin Diesel

The Fast and Furious star is confident enough in his masculinity that he had no issue wearing a cool leather skirt to an award show in 2003. It’s likely that he was being respectful, because the event took place in Scotland, but we’re willing to bet that he more than enjoyed his look that night.

2. Jared Leto

We’ve been lucky enough to see Jared Leto in a dress or a skirt on several occasions and he seems to take pride in it. The extravagant celebrity once tweeted: “Real Men Wear Skirts,” and we wholeheartedly agree.

3. Gerard Butler

The famous actor isn’t unfamiliar with skirts, which he mostly owes to his Scottish roots, but he prefers to not wear them very often. Butler revealed that wearing a traditional kilt comes with some requirements, which once caused him to flash a few people at his sister’s wedding. Looking good always comes with a price.

4. Billy Porter

The Pose star takes every award show appearance as an opportunity to express himself and make others feel brave enough to follow his lead: “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?”

5. Kanye West

As a designer himself, it’s not surprising that Kanye decided to try something new with his wardrobe, and went with a leather skirt for one of his performances in 2014. He kept it relatively safe by having tight black jeans underneath, but we certainly appreciate the effort.

6. Jaden Smith

Jaden’s motivation for normalizing skirts is unbelievably pure: “In 5 years, when a kid goes to school wearing a skirt, he won’t get beat up and kids won’t get mad at him. It just doesn’t matter. I’m taking the brunt of it so that later on, my kids and the next generations of kids will all think that certain things are normal that weren’t expected before my time.”

7. Kyle MacLachlan

MacLachlan once sported a kilt during a New York event celebrating the traditional Scottish attire. Whoever asked the actor to participate is a very smart person, as the Twin Peaks star certainly has the perfect calves for it.

8. Keiynan Lonsdale

The young actor once received a criticizing tweet for wearing skirts and dresses, which said: “Dude, you gotta stop wearing dresses... Come on!!!!” Lonsdale was having none of it and replied to the criticism by writing: “Dude, you gotta stop tweeting me about it and just go try one on yourself. It’s only a piece of clothing and it’s fun.” Keep doing you, Keiynan.

9. Marc Jacobs

The famous designer doesn’t shy away from occasionally wearing skirts and dresses and even made them a staple in his wardrobe. As Jacobs explains: “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.”

10. Brandon Wilson

Wilson is just starting his career in Hollywood, but he’s already doing it right. The actor showed up in a skirt to a premiere of his movie The Way Back, starring Ben Affleck. What made his choice even cooler is that the movie is about basketball and Brandon wasn’t afraid to sprinkle in some femininity along with his on-screen sporty persona.

11. 2 Chainz

Before Kanye wowed audiences with his leather skirt, rapper 2 Chainz was already not a stranger to a similar outfit himself. He looked very natural in a matching skirt and T-shirt look during the 2013 BET Awards in L.A., and we’re definitely feeling inspired.

12. Ewan McGregor

Yet another Scottish actor, Ewan McGregor, has a lot of respect for the traditional kilt and admits to wearing them from time to time: “I wear kilts for special occasions like weddings. It’s our dinner jacket.” He’s even learned to style 2 different types of outfits featuring a kilt, as we can see in the photos above: a more traditional number, and a dressy-casual one.

13. P. Diddy

In 2010, while performing in Glasgow, Diddy knew exactly how to please his Scottish fans. The rapper donned a traditional kilt, which made for a super-stylish outfit when paired with diamond necklaces and a baseball cap. We’re sensing a trendsetter!

14. Misha Collins

Even though Collins was just messing around on the Supernatural set, we still loved how he popped in his princess dress. He should totally look into wearing dresses in public, because we just love an open-minded king who looks great in pink.