Sherman, set the wayback machine to 1984 or thereabouts and let's see what we can find!
And thus, close to 30 years ago I had my first brush with a bloke in a skirt on Boston's metro (the MBTA, better known locally as yhe "T"). It was a white almost ankle-length job, and he was just going about his business like nothing was untoward (which is the way it needs to ne done). That may be what put the seed in my head -- and I didn't take to skirts until 2002 or thereabouts, there being other impediments (family, job, &c.) in the way.
Wind the clock forward into the very early 21st Century, with the aforementioned inhibitors gone, and I dove in head-first and have relished it since -- save for the recent hardening of the line that seems to denote skirts on guys as signifiers that the guy is on the LGBTQWTF spectrum -- which is making me consider ditching skirts for trousers.
I must have been seen by thousands in the intervening decades, and I've always tried to bring the look off with panache and confidence. Direct feedback indicates that I made quite the splash in Savanna, GA last year based on the commentary of my occasional correspondent there.On the second point, none of us really know all the people that we may have influenced for better or worse, we can only do the best we can.
Have I encouraged even one individual to take up the mantle? I have no idea, and likely never will. But, such is life.