Quora is great source for esoteric information. Individual submit a question/subject and others comment. Some of the questions are very deep, as in what do certain religions teach or others, just silly. Many of the answers are scholarly, but most run to just being opinions. There are times when you find a nugget.
I came across this question that relates:
Can guys wear skirts instead of shorts?
There were some long answers but I love this short one by Timothy James:
In Western society, ABSOLUTELY YES! Unless you have objections from your spouse to overcome, the only obstacle stopping you from wearing a skirt is yourself... The biggest differences you'll notice from shorts is that they are cooler, greater freedom of movement, no chafing between your legs, and no crotch seams crushing your genitals. I warn you that once you try on a skirt, you will find it addicting and YOU WILL BE SWEPT WITH A GREAT FEELING OF LIBERATION! I’m hoping that more employers like those that manage Hannover’s public transportation (Germany) will allow men to wear skirts to work. (Hannover: Busfahrer tragen) If you go for it, you'll enjoy it! Best wishes.
Have you tried it? What reaction did you get? I am not talking going out "En femme", but just casually wearing a skirt.
Here is a treasure trove of photos - Men wearing skirts.