15 Celebrity Men Who Have Broken Fashion Stereotypes By Wearing Skirts and Dresses

Fashionistas have had an interesting few weeks. At the Venice International Film Festival, the Met Gala, and New York Fashion Week, there are plenty of eye-catching celebrity outfits that keep your eyes peeled. Some outstanding moments have included artist Frank Ocean carrying about a robotic green baby and actor Timothée Chalamet dressed as the world's sparkliest Mafia don - but another thing that stuck out is how many extremely masculine men have been stepping out in quite feminine dresses and skirts.
It appears to be a true breakout trend, with everyone from rapper P. Diddy to famed actor Gerard Butler getting in on the action. It has proven that men wearing skirts is no longer something that only appears in history or in minority cultures anymore. Now, it's normal for both men and women to wear skirts, but seeing the following celebrities gorgeous in their dresses and skirts still gets you excited! Keep reading for more detail!

#1 Misha Collins

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Misha Collins wore a princess outfit while having fun on the set of 'Supernatural'. Fans also left comments encouraging him to dress similarly at the movie premiere.

#2 P. Diddy

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P. Diddy, whose real name is Sean Combs, seemed determined to charm his 1,500 fans. In 2010, the male rapper pleased fans during a performance in Glasgow, Scotland when he used a kilt as a highlight of his outfit. Dressed in a black cap, jacket, and boots along with his kilt, he said: ‘You’ve got to be a real man to wear this.’

#3 2 Chainz

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2 Chainz continues what seems to be a trend in the rap industry. And he looked so confident in leather skirt at the 2013 BET Awards in L.A.

#4 Marc Jacobs

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Of course, we can't ignore Jacobs's appearance in a polo dress and mesmerizing ankle boots. The famed designer has made skirts and dresses a mainstay in his outfit. "I discovered how nice [skirts] felt to wear," Jacobs explains. "They're comfortable, and wearing them makes me happy, so I bought more. And now I can't stop wearing them."

#5 Kyle MacLachlan

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MacLachlan once wore a kilt to a New York gathering honoring traditional Scottish attire. Whoever requested the actor to take part in was a very wise person, since the Twin Peaks actor had the right calves for it.

#6 Kanye West

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The left-hand job is a designer, so Kanye West has to quickly choose a leather skirt to match his brother. During the 2014 show, he wore jeans to ensure privacy, but we certainly appreciate the effort.

#7 Gerard Butler

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Although he doesn't wear skirts very often, the well-known actor wasn't afraid of skirts, which he attributes to his Scottish heritage. Butler noted that wearing a traditional kilt has some restrictions, which resulted in him flashing a few people during his sister's wedding. Looking nice usually comes at a cost.

#8 Vin Diesel

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"Fast and Furious" star Vin Diesel wore a leather skirt to an awards ceremony in 2003. Since the event was held in Scotland, he wanted to wear clothing that showed cultural respect for them, but we were willing to bet that he more than enjoyed his look that night.

#9 Jared Leto

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We've had the pleasure of seeing Jared Leto in a dress or a skirt multiple times, and he appears to take satisfaction in it. "Real Men Wear Skirts," the flamboyant star once tweeted, and we agree with him.

#10 Billy Porter

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Billy Porter consistently beats many other female celebrities on the red carpet. He always appeared in the most sophisticated, most sparkling, and biggest dresses. He once shared: “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?”

#11 Jaden Smith

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When it comes to his style, Jaden Smith has defied outdated gender norms. This 19-year-old style hero shows that there is no need to dress along socially imposed gender lines by sporting an equal quantity of sloppy denim and layered dresses and skirts. Wear what makes you happy instead. "If I Wanna Wear A Dress, Then I Will, And That Will Set The New Wave...#ICON," the celebrity tweeted last week. And he does that.

#12 Keiynan Lonsdale

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Lonsdale, who rose to prominence as "Kid Flash" Wally West in "The Flash", is now best recognized for his performance as the Oreo-obsessed Bram in the gay teen rom-com Love, "Simon". The film has been warmly appreciated globally, resulting in a slew of prizes and red carpet appearances for the cast.
The 26-year-old actor has made several of these appearances in a variety of stunning dresses and skirts.

#13 Brandon Wilson


Brandon Wilson is just starting his career in Hollywood but has already made a splash. During the premiere of 'The Way Back', he wore a pleated skirt. Interestingly, the movie is about basketball, but Brandon isn't afraid to bring in a bit of femininity.

#14 Ewan McGregor

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Another Scottish actor, Ewan McGregor, admires the traditional kilt and confesses to wearing one on occasion: "I wear kilts for special occasions like weddings. "It's our dinner jacket." He's even learned to style two other sorts of kilt attire, as shown in the photographs above: a more traditional look and a dressy-casual one.

#15 Jonathan Van Ness

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Van Ness, one of the stars of the makeover show "Queer Eye", enjoys experimenting with his red carpet outfits and frequently shines in bold gowns. Jonathan is smashing gender stereotypesone suit at a time, and we love it.
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