(...even though politically I'm a far-left liberal Democrat.)
Rightly or wrongly, fairly or unfairly, MTF ladies have been stigmatized as not knowing how to dress well. I feel I need to prove this assumption wrong. The stereotype says we overdo the miniskirts and makeup, we don't dress appropriately because we wear the male impression of how women dress, not how women actually dress in real life. This criticism is leveled more at crossdressers than transsexuals, but many of us TS ladies have come in for similar snipes as we work on refining our wardrobes. I think it contributes a lot to the discomfort many TS women feel for male-identified CDs and the wish to distance ourselves from them.
The most frequent result I've seen is TS women preferring to dress down and avoid femininity. I wish I had a nickel for every TS woman who's told me it's better to wear jeans/sweats/sneakers and no makeup or heels. On the theory, I guess, that ordinary everyday women don't wear dresses to the Safeway or K-Mart. So if we imitate their example, we'll just blend into the crowd and be safe from misidentification as crossdressers.
That isn't good enough for me, because I love to be feminine and pretty-- as in fact many genetic women do. But while I don't want to be boring and frumpy, I need to look genuine, not CD. So what works for me is to dress in an elegant and tasteful feminine style. It helps that I dress age-appropriately. For office work I wear very conservative knee-length skirt suits a lot, as well as slightly trendy and figure-flattering but understated dresses. I also favor long skirts a lot, especially with simple long-sleeved microfiber tees, it's a slimming look. Modesty is to my advantage. Being a woman doesn't mean you have to show skin. I can glide very gracefully in 3-inch heels but have never gone higher than that. I avoid exaggeration of any kind.
I like to wear miniskirts, but rarely do, because minis have just become too stereotyped as worn by balding overweight thick-legged hairy-bodied masculine-featured CDs with beard stubble who are hopelessly clueless about style. Since my body is tall and broad-shouldered, I go for soft understated styles that feminize me the best and emphasize my good features. I wish I felt able to wear miniskirts more, but I just don't think it's advisable usually. Instead, I capitalize on tasteful elegance. Good for the ol' self-esteem. I always get compliments from other women on my style.