I used to try and pretend I was confident when out dressed but it wasn't working and I knew it. I felt like a fraud and everything from my body language to my facial expression advertised that discomfort. Only now in retrospect can I tell the difference.
Now I think: who in blazes cares what about the opinions of other people. They know nothing about you or your life. You need to be true to yourself with the understanding that you are not breaking any laws be they civil or moral. You are treating gender dysphoria or simply have a penchant for crossdressing; either way it pays to be comfortable in your own skin.
Smile and be happy. Engage others in conversation and you will be amazed how your confidence soars. If nothing else you will be doing outreach.
Recently a US poll revealed that only a tiny fraction of Americans admitted that they knew a transgender person but of course that statistic is wrong. Many of us live in the shadows and carry our dysphoria with us like a ball and chain (think Jacob Marley from a Christmas Carol). The key to our release is entirely in our hands and what holds us back is fear of the unknown.
Coming out and how much you do it is up to you. I think that the barometer for this might be feeling good about yourself and releasing your soul from a self-inflicted purgatory.
I grew up repressed due to my religious upbringing so my path was extra long. Perhaps yours might be considerably shorter.
If you are stuck thinking that being transgender is the result of some sort of deviance and nothing I have said in this blog has convinced you otherwise, I invite you to keep reflecting. I am convinced you will arrive at the right place if you ask the proper questions.
When I am out as Joanna I am not pretending to be someone else. I am simply being who I am and there is no better gift to give yourself than that.