11 Celebrity Men Who Have Rocked Skirts and Dresses in the Past

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It’s not common to see a man wearing a skirt or a dress, and when a man chooses to make a traditionally feminine piece of clothing part of his wardrobe, it often gets a lot of attention.

Men wearing skirts and dresses isn’t exactly something new though. It isn’t even something rare in some cultures. For example, in Scotland, kilts are commonly worn by wedding guests, by athletes and by dancers.

Scroll down to discover 11 celebrities who have rocked a skirt or a dress publicly at least once. You might be surprised who is on this list.

  1. Harry Styles

    The most recent celebrity to get press for wearing a dress is Harry Styles who wore a Gucci gown on the cover of Vogue.

  2. Keiynan Lonsdale

    In 2018, the actor wore a dress to the MTV Movie TV Awards. In his acceptance speech for Best Kiss, he said, “I just want to say to every kid: You can live your dreams and wear dresses.”

  3. Seth Myers

    In 2012, comedian Seth Myers wore a see-thru Marc Jacobs dress to host the Fashion Awards. Yes, it was supposed to be funny, but he also admitted to Conan O’Brien that it was “the nicest thing I’ve ever worn.”

  4. P. Diddy

    In 2010, Diddy wore a traditional Scottish kilt while performing for fans in Glasgow, Scotland.

  5. Jonathan Van Ness

    The Queer Eye’s Jonathan Van Ness has worn skirts and dresses on numerous occasions including awards shows like the Emmys.

  6. James McAvoy

    Scottish actor James McAvoy is proud of his heritage and shows it by wearing a kilt featuring his grandfather’s tartan.

  7. Jared Leto

    According to Jared Leto “real men wear skirts,” and he has been spotting wearing a skirt or a dress on numerous occasions.

  8. Patrick Stewart

    Patrick Stewart wore a kilt to the Edinburg International Film Festival.

  9. Vin Diesel

    In 2003, Vin Diesel showed up at an awards show wearing a leather kilt. Granted, it was in Scotland, but still.

  10. Jaden Smith

    In an interview with Nylon magazine, Jaden Smith explained that he wears skirts to promote change for the future generation. “in five 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.”

  11. Billy Porter

    Billy Porter likes to “challenge expectations.” If he wants to wear a dress, he will.