7 Famous Guys Who Look Absolutely Killer In Dresses And Skirts

Sometimes I’m a little alarmed by how much cis-gender dudes shudder at the thought of wearing a dress or a skirt. I know, they’ve been socialized to think that they’re inherently feminine, and wearing one would be a blow to their masculinity, which would apparently be a fate worse than death for many. Well, trousers were thought of as inherently masculine for a while, too, but women started wearing them (even if their school objected) and the rest is fashion history. But men wearing dresses or skirts? In the western world, that’s just inconceivable unless it’s a kilt or something, which only technically counts here.

For the most part, if a woman glamorously rocks a menswear inspired look, it’s considered edgy and daring. If a dude wore a glamorous dress, he’d be considered…weird, funny, gay, mentally deranged. And why? Because objects of femininity are really that toxic to some. It’s why we’re mostly chill with women looking dapper in a suit and tie, but cringe at the very idea of a man wearing a gown. Masculine, good, strong; feminine, bad, weak. Yawn. IDGAF, I’m here for dudes wearing makeup just as much as I’m here for dudes rocking a dress. In fact, there are loads of men out there who rock a dress like a champ. If you need more verification in the source of celebs, look no further: Here are seven famous guys who look absolutely killer in dresses and skirts.

Jaden Smith

Not long after he was featured in Louis Vuitton's womenswear campaign sporting a dress, Jaden spoke with British GQ about gender norms and fashion. "I don’t see man clothes and woman clothes," he said. "I just see scared people and comfortable people." Judging by all of the nasty comments he receives anytime he rocks a dress or a skirt, there are a lot of scared people out there.


Ezra Miller

Honestly, I forget how much I love Ezra Miller unless I'm staring right at his photos in Google Images for way longer than anyone should be allowed to stare at someone's photos in Google Images. Anyway, this self-proclaimed queer actor and overall spooky babe has been known to wear some pretty daring outfits from time to time. A shoot he did for Paper Magazine a few years ago was no exception. Seriously, like...this is just unfair. He is killing this dress, but TBH this dude can wear a burlap sack and look gorgeous.

Paper Magazine

Yung Thug

YUNG. THUG. IS. A. GIFT. This rapper graced the cover of Dazed and an editorial rocking a dress...and looked beyond killer. The reason I'm so hype about this is that hip hop is a field in which machismo masculinity dominates, so for somebody eccentric like Yung Thug--a dude who is known to wear leopard print dresses just because he can--is getting so much love in that kind of environment just fills me with warm and fuzzy feelings. We need more folks like this out there, thriving.

Dazed Digital

Kurt Cobain

Confession: I think it's really sexy when a guy is playing a guitar, screaming into a microphone, and rocking a dress. Maybe it's a secret fetish of mine, I don't know, but what I do know is that Kurt Cobain definitely pulls it off in an effortlessly sexy, energetic way. This wasn't just some one off either; he wore them several times at concerts, on magazine covers, and in candid photos. From floral '90s nightmares to borderline lingerie, the dude knew how to rock a dress.


David Bowie

The late, great David Bowie was known for his iconic chameleon-like style, shifting his look for every musical era he undertook, transforming into a new character before our eyes. It's nice to know that dresses were never seen as going too far for him. Dude looks like the subject of a 19th century painting with a hint of retro French schoolgirl and I am absolutely here for it.

David Bowie/The Man Who Sold The World

Marc Jacobs

Marc Jacobs actually wears dresses and skirts not-so-irregularly. From hot pink maxis to leather minis, this dude knows how to work flawlessly rock traditionally feminine silhouettes like a champ.


Iggy Pop

Rock icon Iggy Pop looked classy as hell when he was featured in a FckH8 campaign a few years back. There's little indication that Iggy dons glamorous dresses like this on a regular basis, he still gets props for boldly embracing this look for a progressive anti-hate organization.


Do you wish that more men found a way to rock dresses and skirts? Do you think that that would Tell us in the comments!

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  • TopCat

    Ashley, I am in no way famous, but I do absolutely agree with you that men should wear dresses and skirts without it being seen as odd or ‘not normal’. I am a straight guy and I wear dresses, skirts, knitwear, shoes – all designed for women, whenever I can. For a start, I dress for comfort and style and I certainly achieve both when I am wearing my dresses and skirts. Another reason I love wearing clothes designed for women is that there is so much choice – mens clothes are positively boring. I own some gorgeous ‘coatigans’ and long cardigans, but will you find these in menswear departments – not a chance!!

    I would love to see the day when all clothing becomes’ gender neutral’, but I fear that is a very long way off! A woman wearing clothes designed for men is considered perfectly acceptable – and I have no problem with that. However, it is very much ‘double standards’ when it doesn’t work the other way around.

    How I wish more men would take the plunge and try wearing a skirt or dress and finding out just how comfortable it is.

    • martinbarrdavid

      Abosolutely agree!