It used to be that whenever I saw an article about cis men wearing clothes that society views as exclusively for women I would become optimistic about the de-genderization of clothes. Men wearing skirts? Heck yeah! Men painting their nails? Heck yeah!
I don’t want to be cynical but I don’t feel the same optimism that I used to. I don’t necessarily think that when a celebrity wears a skirt or a dress that it means that the world will collectively think it’s acceptable for any cis male (basically non-famous cis-males) to wear the same outfit.
When Brad Pitt or whomever wears a skirt I think most people chalk it up to as celebrities being celebrities or trying to draw attention to themselves or shock people. “Celebrities are weird” is a pretty common response.
A movie star wearing a skirt to a film premier is one thing. Your coworker wearing a skirt to the office is another. Your buddy wearing a skirt to the bar to watch football is also another.
It miiiiight be, well, not normal for an actor to wear a skirt, but perhaps it will become less uncommon in the future. However, I think there’s a long, long road ahead until it becomes “acceptable” for a dude to wear the same skirt.