I'm probably in the minority, but I like to be well-dressed in male mode. I have a fairly high profile job which requires me to meet with attorneys, CPA's, corporate exec's, and the occasional politician, so I have an extensive male wardrobe which includes several expensive suits by Polo, Oxxford, Brooks Bros., and the shirts, ties, belts and shoes which go with the territory. I pay attention to how I look, and there have been days when I spend fifteen minutes trying to decide which tie/shirt combination I want, and tie/retie my necktie several times to get the lengths perfect. On weekends I like to wear Levi 501's, cashmere sweaters, turtlenecks, and good sneakers or sandals.
My female wardrobe is much more casual, but I still have more items from say, Harve Benard and Ralph Lauren than from PacSun or Old Navy. I think that my biggest problem in selecting clothes is trying to remember that I should be wearing clothes that would look good on Caitlyn Jenner rather than clothes which would look fabulous on Beyonce. I would love to be able to wear miniskirts or party dresses and super Femme lingerie, but instead I just pretty much go with what a late fifties/early sixties professional woman would wear. My dreams are pretty small, huh?