While I have been out of work I have joined a walking group that meets in my area about once a fortnight. Most of the members are retired but not all and walks tend to be fairly easy terrain and ten or twelve miles in length. I have been meaning to post here to say that all the walks I've joined them for have had at least two kilted men on then (apart from me).
The first time I joined them I took a kilt, a pair of Craghoppers walking trousers (with removable legs) and my Fat Face wrap skirt, so that I could pick the appropriate style of dress to avoid causing ructions in the group while still seeking to join it. There were two guys in Sport Kilts so I bit the bullet and wore my skirt. It received several compliments from other walkers, both kilted and trousered, and no unsupportive reaction at all so I have worn that for all the subsequent walks too.
I went on one of the walks last Friday with the largest party I've yet seen, 20 walkers in total. Of these four were in kilts, one was wearing a skirt bought from a charity shop then split up one leg seam to allow a full stride and one had a "mini kilt" which was actually a short, pleated tartan skirt with an elastic waistband. As usual I had my wrap skirt but there was also a chap (in his early 50s) in a denim miniskirt, about 13" I'd guess. He wore it with a t-shirt, sweater and denim jacket so that he could vary the number of layers to suit his temperature through out the walk. Two ladies walked with us, one of them skirted the other in a just below the knee dress. In total that meant half of the group were skirted, eight of them men!
Most of the guys changed into jeans or shorts before we went in to the pub after the walk for a meal but I and the chap in the denim skirt did not change. We drew a few curious looks from other patrons and from the staff but the only remark I overheard was one waitress (about 18 years old) who commented to another that she thought it was good that some men were not afraid to wear something different. Unfortunately she then spoiled it by adding "shame they are both so old"

Given the discussion of rain skirts for carriage driving and shooting elsewhere on the forum, I am starting to wonder whether the practicality of skirts for some outdoor pursuits may be a driver that helps to bring men's skirts into the public consciousness.
Have fun,
Ian.
Edited to fix typos - Ian.