I agree with Becky- get a makeover at/done by a trans specialist and go out with them or alone to a trans-friendly place afterwards. I did this my first time (in May) and it was exhilarating! I met some other CDers and she did such a good job with the make-up and styling my wig that my own family would not have recognized me if they saw me and so I felt very comfortable at the trans-friendly bar and then even walking around the downtown area afterwards. I feel very confident I will do it again when the need returns and am more comfortable about shopping for fem clothes in drab because of that experience.