I am one of the “auld yins” who has, just around two and a half years ago, discovered the comfort of skirts. I have had a kilt which I’ve worn on a few occasions each year (Xmas, Office parties, Ceilidhs etc) and have had it since I was 50. I have noted my “first time” in a real skirt (a denim miniskirt) elsewhere so no need to repeat it and have had many other “first times” such as bus journeys, train journeys, air flights, taxis, shopping at my own local supermarket, shopping in that man-only domain of DIY shops, charity walks and so on.
In all the reaction has been absolutely nothing to speak of – just a few double-takes and a couple of :-O’s from a couple of elderly ladies was extent on the negative side.
On the positive side, however, I have had women say, “Wow!” “Looking good” “Man in a skirt! Cool!” “You’ve better legs than me in a skirt”
as well as many thumbs up from others which is terrific for confidence-building. 
My son thinks it’s cool but my wife, unfortunately, doesn’t like the idea at all – she’s not even that keen on the kilt either, but does accept it for very special occasions (30th wedding anniversary for instance and Xmas).
I find the kilt rather heavy for everyday use so read up on various web-sites about skirts – not sure how I came across it initially but think it likely to be in a Google search for kilts which brought up links to various man-skirts sites.See you around
- and it was very positive.