I have not dressed to "pass" in over a decade. I wear articles of women's clothing becauce I like them or they are comfortable. I try to look nice, and often look better than others I see. Admittedly, my styles is mostly androgynous (flats w/jeans, etc.). It only matters that you are comfortable with yourself. I also feel that by being a bit obvious I may give others who see me encouragement to be more bold. I have not had a bad experience yet.