Troph- I will ask the following seriously looking for an opinion, not to mock, and apologize up front if it is offensive. It's not intended.
Is there a time period when someone is transitioning that if they are still very masculine looking, that unless they are looking for "stares" or "a reaction", that they shouldn't dress outwardly in traditionally female clothes? To many, it could almost seem that they want a confrontation whether it be a misunderstanding or from someone being a jackass.
I think that you and I have talked about things before at the other site, not about whether or who is right or wrong, but for many of us old folks, what a change this is to our world view in how we were brought up, trained from a religious background, to even a medical/psychological professional standing. In some ways, trans is harder to comprehend than orientation, because while I cannot judge or say to whom you are attracted to by gender, the outward change of clothing or identity still seems very culturally oriented or biased. Think of a society were men happened to wear skirts and women wore suites or pants. It doesn't mean anything other than local cultural norms. With power dynamics changing so much in the past 20-30 years in the workplace or authority, this makes the trans idea or position (without a non-normative orientation) ever more difficult to understand for many. Again, I'm trying to understand, not judge or bust balls (yea, that was on purpose... lol)
As an aside, years ago I had a gay friend tell me, and I'm not sure that I fully agree or not, that what scares most traditional uptight folks is not the outlandish Dore Street Fair gay pride parades with the over the top craziness. That is easy to make fun of. He said what scares or is hard to accept is the normal couple of dudes or chicks who buy the house next door and get up and go to work and mow their lawn and walk the dog just like me.