I think my thing for wearing skirts has always been in me just suppressed by social norms for most of my life. I have always worn clothes that are different or just plain "out there" since my teenage years (I am now in my early 50's) really bright colours, unusual items and just stuff that people see as different. I just see wearing skirts as a natural progression of my clothing choices.
I love wearing skirts, i love the feeling of freedom of my legs! it has to be bare legs for me, i don't subscribe to the tights thing, that is just too feminine for me. The same goes for shoes, i don't like wearing women's shoes (I have experimented but it's not for me). I guess I am happy with just being a bloke who wears skirts.
My wife and kids see me in my skirts around the house regularly as just accept it as me. I have been out in a kilt (black) to Camden Market with my wife who was a lot more nervous that I was. We got the underground from my local station and apart from a few looks there were no issues throughout the day.
I have a number of proper skirts now but haven't been out in public in any of them. I am not too worried about being seen, for me it's about small steps with my wife who accepts my skirts but is worried about the reactions of people towards me. Small steps but i don't think it will be too long before my local supermarket it treated to a bloke in a skirt
