isn't this a question about why we dress and where we go too?
If a person is dressing in the privacy of her home, then whatever gives her that feminine, comfortable glow is what's right. If you're going out shopping, to a club, or a party, then being appropriately dressed is only good manners and good taste.
I have sexy outfits that I wear in the boudoir and for my own private naughty photo shoots, I have blue jeans and chambray shirts for outdoors, and cocktail dresses both long and short. Would 55 y.o. G Lady in good shape wear a fishnet mini to the party I'm attending without looking ridiculous? If "Yes," then so can I, if I think I can pull it off (what's that phrase, "Mutton dressed as Lamb?").
I try not to go overboard on the CD/TV weakness of shoes, too. Most gender women who are 5-11 wear flats or low heels, and I do too, except when I'm trying to look like a 'Ho. Nothing screams "party girl" quite as much as a pair of inappropriate shoes. As a matter of fact, I've never quite found a satisfactory answer to the question of when six inch heels are appropriate, although I think that I got a clue when I bought a pair of lace-up fetish boots (white wet and plastic) and got a complimentary whip inside the box http://www.crossdressers.com/forums/...lies/happy.gif
You have to play to your audience, too. I live in Manhattan, most of places I go to can be fairly outre' (a primary reason I moved here from the midwestern 'burbs to put up with $3500 a month apartment rents), and some of the stuff I see will not play in Peoria anytime soon.
I just wish there was some way to deal with my voice as easily as the clothes. When I'm not careful I sound like William Warfield singing "Old Man River."