As a 21st centurary man, I don't feel ashamed in a skirt but I do find it difficult to find one that matches the colour of the planes at my club. Ops can't always tell me which plane they'll allocate me ahead of time and I've had some terrible fashion disasters recently.
I've also got a rather slinky, black, off-the-shoulder number with a large split up the side. Problem is I have to 'hitch' it up to climb on the wing and having hairy legs it can be a bit unsightly.
-S