I'm joining this party way late, and to be honest, haven't read through the entire thread, but I thought I'd post my $.02 anyway
I think many times, people tend to dress towards what their own mental images of "femininity" are, and more often than not, it happens to be when they first started dressing which, for some of the older ladies could possibly be a different "style" than what is currently the style. Obviously that's not always the case, and there are always tons of exceptions to the rule, just saying I think that's one of the reasons.
Another, is depending on several mitigating factors (level of comfort, whether out or not, ability to explore new designs etc..), people might try to pack in as much femininity as possible during every dressing session. This would mean turning away from anything that is "mannish" or what have you with skirts, heels, bras, camis, etc taking center stage. I think for the most part, CD's are more often than not seen in skirts rather than pants, and are in camis or tops like that rather than tshirts.
Anyway, just my thoughts...
