Easter is approaching and I think this offers a perfect opportunity for a boy who is experiencing femininity as a novice to have a safe day outside.
A religious service can be a perfect first step in this regard.
1. A service lasts only about an hour and thus there will be no issues like restroom use that could be embarrassing.
2. If you attend a service not near your home, you will not be recognized.
3. The service is nonjudgemental (anyone can attend) and you can sit quietly by yourselves and not interact with anyone if you prefer.
4. He will not appear out of place, even when dressed elaborately, on a holiday like Easter.
If you want to develop your thoughts further, I highly recommend Viola Voltairine's blogs, as well as Elise Sutton and Lady Misato's websites, and the book "Men Are Not Cost Effective" by June Stephenson, Ph.D.
Thanks for posting here and good luck!