I think the magical thing about crossing genders, is that if one chooses not to "pass", then they will draw attention. If one is insecure with one's look, then the attention will be unwanted, but if one sees the attention as opportunity...to spiritual touch others, and to communicate the magic and wonder of life, then it is a gift to be honored and enjoyed.
I enjoy appearing differently gendered, but at the same time I am very careful about my appearance. I dress very neat, very clean, sometimes sort of conservative, but much of the time in fashion that will draw attention, but still be appropriate. In this way people see me as approachable, which I really enjoy, and when I go out I always have "divine appointments" with at least one person. I define a "divine appointment" as a spontaneous conversation developing with a person that is more than the superficial...a time of "touching" each others soul, and a connection is there.
In these interactions I find I can speak joy and wisdom into other's lives, as well as be blessed by their spirit and wisdom also. I have made so many wonderful connections just by being "present" in the moment
It is like participating in a world where all things are possible.
It is indeed a magical world.