dress for the occasion. I do not prefer dresses. I don't have any need to wear one. However, I would like to get to the point where I could pull it off ... umm, rephrase .. look good in one. After a recent photo shoot that my wife put me through, I'm not ready. I have seen many women (trans or cis? I don't know and it doesn't matter), anyway, I've seen many wearing dresses that look awful on them and again others that look great. It's all about the style and appropriateness. How you carry yourself, I'm sure, has a lot to do with it. I don't feel comfortable so that probably has a lot to do with it.
summation ...
I much prefer slacks and jeans (woohoo skinny jeans).