Fashion has always been an evolving landscape, yet society remains surprisingly quick to draw lines around what men and women “should” wear. When a man steps out in a skirt or a dress, the reaction is often one of judgment or confusio
1. Vin Diesel
The Fast and Furious star proved his confidence is unshakable when he donned a leather skirt for an award show back in 2003. While the choice was likely a nod to the event’s Scottish location, Diesel carried the look with the kind of ease that showed he was genuinely enjoying the bold style choice.
2. Gerard Butler
Staying true to his Scottish roots, Butler is well-versed in the art of the kilt. While he looks effortless in traditional attire, he’s shared humorous stories about the “occupational hazards” of the garment—like accidentally flashing guests at his sister’s wedding. For Butler, looking this good sometimes requires a bit of extra caution.
4. Billy Porter
The Pose icon views the red carpet as a canvas for political art. Porter uses his high-fashion gowns and skirts to dismantle the very idea of traditional masculinity, constantly asking the world to redefine what it means to “dress like a man.”
5. Kyle MacLachlan
The Twin Peaks star brought a touch of sophistication to the kilt during a celebration of Scottish culture in New York. Sporting the traditional look with ease, MacLachlan proved that the silhouette is timeless and adaptable to any style.
6. Jonathan Van Ness
The Queer Eye star is a master of the “gender-bending” red carpet look. Van Ness frequently chooses daring dresses and skirts, using his platform to champion the idea that clothing should be a source of joy and authenticity, regardless of gender.
7. Misha Collins
Though his foray into “princess-core” began as a lighthearted moment on the set of Supernatural, the look resonated with fans. Collins’ willingness to have fun with traditionally feminine colors and styles serves as a reminder that a truly open-minded perspective is always in fashion.