Actually it is not always bad fashion sense. Sometimes it could be good, it is just knowing how to pull it off. There is an entire cult of fashion in Chicago called "grandma chic". Young women who dress as old women. Kid you not.
Much of it also cultural and subcultural. Since most trans people often lack this perspective due to social isolation it often leaves them in a bit of an odd place with regards to how they dress. They literally lack this perspective, or it may be they have this perspective.
As strange as this sounds this is a big part of the reason younger trans people transition much better. They often are bit more tied to some subcultural perspective and are part of a culture which is SIGNIFICANTLY more tolerant of TS. It is easier to assimilate.
Additionally, as I stated earlier, sometimes there is no interest to be beautiful or pretty (I have no such interest). I was watching one of these fashion shows where they ripped apart a tomboy mountain climber, I was pretty deeply offended, because there was nothing wrong with this persons clothing or expression, she was just more outdoorsy than most women. Kind of upset me because it was very narrow minded.
With that being said, I don't think I would be caught dead in some womens clothing. It does not fit me or my personality.
There is really no "norm" in female attire or any attire. It is honestly finding what fits you and your personality. We all have a bit of an adjustment period with regards to that, and it takes some people more time than others.
Personally I am in my own almost stereotypical adjustment period.
