This is one topic I wrestled with in the past week but I was able to resolve it in one word - subjectivity. Each and every person we encounter has a different definition of what a woman is and that translates further into what will pass and what won't. There are those that we pass with easily and fit in as women and then there are those with such rigid definitions that many cis women would have a hard time hitting them.
In the end, I think we have to get to the point that it just doesn't matter. We transition for us, our mental well-being, not what the world offers in return. I will be the very first to admit that proper gendering and such is very rewarding internally but in no way can I control how people think.
Just this week at Wallyworld. One cashier chatted with me like we went to high school together, the next one was clearly disturbed by me, totally rigid and wouldn't say a word. I just let it go, which is something only a few weeks ago I would not have done. I'm glad I am working through this part and hopefully it continues to be less of an issue for me.
When you consider how much many of us wrestle with transition and all that it means, its no wonder that cis gender folks who have no understanding of the oddness we feel have problems accepting we are what we say we are.