Might there be a happy medium? Dressing like a hooker for a trip to the mall or grocery store might give a gurl a thrill but it almost certainly will reinforce negative stereotypes in the eyes of beholders. On the other hand, I'm old-school enough to think it's a shame some GGs (many, actually) have appropriated male dress (baggy shorts, sloppy tshirts, etc), and maybe they could make a bit more effort, at least as far as everyday casual dress is concerned. It IS possible to be comfortable, feminine and stylish all at the same time, after all.
There's also the matter of age and fashion. I hate and refuse to accept the sort of PC notion that older ladies aren't allowed to be stylish and maybe even *gasp* a little young-at-heart in their fashion choices. I don't mean ****ty, or even clubby, in mainstream settings, just style and flair. Whenever I see a 50+ GG in a retail or business setting who has kept herself in shape, thinks makeup and hair are worth the effort, wearing heels and a skirt *gasp* a little above the knee, I want to rush over, give her a great big hug and thank her profusely for keeping femininity, style and sexy alive. Then ask her where she got those amazing earrings. :D
So I guess it depends on whom a CDer is trying to emulate and fit in with, right? If I have to dress like an asexual slouch who gave up a long time ago, well, I guess I just won't fit in. But I have evolved a beyond the it's-a-sex-thing that prompted many of us to explore CDing in the first place and learned the value of presenting as a sane, down-to-earth, interesting human being who isn't a threat or embarrassment, who might actually be worth getting to know and understand. And who believes style and a youthful spirit aren't mortal sins.