I always dress appropriate for the occasion, and for my demographic:

If it's shopping at the mall or the grocery store, or saturday night at the movies ,it's usually jeans, and a woman's top and a scarf, boots or flats or sandals. I still feel like I'm on Team Woman

If it's meeting a friend at a restaurant, it's often a dress or skirt...same with footwear mentioned above.

If it's something big or glam or fun, it will be the LBD.....the little black dress or something sexy with heels.

I'm going to say something in defense of the first, that is dressing casually gives me unlimited freedom anywhere without being gawped at. I feel like I blend right in, and that is a very reassuring feeling. It may not be as much fun as wearing a sexy dress & heels, but I am out in the public eye, and to tell you the truth I prefer it way more than just wearing my guy clothes.