H.W.
I have the perfect solution; I rarely wear skirts. I have no sense of fashion, either, so my solution is not going to work for everyone.
Shorts for M.. If I do wear a skirt, it usually hits M. right above the knees and is a-line or something else that's not clingy. (at nearly 42 I'd feel ridiculous in a short skirt, but that's J. M....)