I personally think "passing" is overrated. I used to worry about it when I first started going out, but soon realized that there was no way I would pass in all situations. Nothing ever bad happened as a result of being "read" as a crossdresser, so I stopped being concerned about it and started having a good time. I found that I actually had more fun when people read me as a crossdresser and gave me an opportunity to talk with them about it. I've cleared up a lot of misconceptions about crossdressing with these one on one encounters. It doesn't bother me if a couple of people walk past me and I hear one say to the other, "That was a man in a dress" - as long the other one replies, "Yes, but doesn't he look good in it."
For me, crossdressing is about going out and having fun with it.
