I was reading Femulate the other day where Stana was commenting that some of her skirts are perhaps a little too short for street wear. This reminded me of a conversation I had at my support group meeting the other day, where we were speculating as to whether the taste for very short skirts is restricted to cross dressers, or whether this taste is shared by trans women. Certainly I see very few GGs my sort of age wearing anything particularly short, and when I do I will admit it does get my attention. Well this article http://www.huffingtonpost.com/2011/10/21/celebrities-without-pants_n_1024544.html suggests that at least some celebrities are going for the very short look.
Somehow what is worn below the short skirt/shorts/ whatever seems to make a difference, I have a GG friend who likes dresses but hates her legs, so she wears the dress over a pair of jeans, this is a very individual look, and she has made it her own. I think that a dress so short that it's a tunic is fine over leggings, but not over sheer tights, shorts or culottes will not show your underwear so maybe a little more latitude is allowed then. I also think that the shoe choice makes a difference, I can't get used to the current fashion for ballet pumps, but there is a definite trend for very short skirts, opaque tights and ballet pumps, for street wear, the same outfit with heels would not be appropriate, but I'm not sure why. It seems very difficult to stay the right side of the line between classy but sexy and slutty.
I think I am coming to the conclusion that it is complicated, and I will just have to show judgement for each individual outfit.