In the main world individualism is highly prized, Unfortunalty in the Charedi world it is not. Everything is seen as black and white.
Not everyone can be a charedi. Its a tough life for many. I know many love that life but obviously some dont.
You are not a Rasha if you cant be a Charedi.
I think you get this idea, but are worried about your community and you will be perceived. I think you need to forget about your community and think about your son.
It is not an Aveirah to wear Jeans. If thats what he wants let it go for now. You have to think now, whats against Hashkafa and whats against HALACHA. Fight the Halacha issues and let the Hashkafa ones go for now.
I think you sense this from your posts, but seem unwilling to take the jump