I can relate to being self conscious. I took trips to be out of town to be myself full time.
It did seem easier as time passed. I gained more confidence. Yet, I felt that many were scoping me out, so I was careful and stressed, but this too mostly passed as I seemed to experience fewer unpleasant moments.
So, the more you have opportunities to present and be yourself in safe situations, and experience this, it does become easier to be out and about. Being with others you know may help for sure, if they are accepting. So even a local day with these others can be helpful too.
I wish good experiences for you as you venture out. Be safe and try to enjoy these times.