There first time is always the hardest, but once we realize that we survived it, and even enjoyed it, more times will come.
There are a myriad of ways of going out in public, from undressed to fully en femme. Just try different things and see what works for you, and most importantly, what you enjoy. In time, quickly or slowly, its up to you, you will find your comfort level and what you want to challenge and what you don’y. There is no right or wrong, just what makes you happy.