Well after dressing at home and fantasizing about wearing womens clothing in public for many years finally in my early fifties I shaved my facial hair and out I went shopping fully dressed head to toe. I do not think courage had anything to do with it for me it was just something I had to do after many outings I became almost addicted to the submissive feeling of being out in public wearing a dress and heels.
For me real courage would be telling my wife about my desire to dress in womens clothes.