I do agree that for kiruv sometimes we put somethings aside to maintain the more important matters.
So, considering the fact that I don’t know the OP and his kid and (I’m assuming) you don’t either – do you agree that there is a reasonable possibility that it might be a good idea to just “lay off” the jacket/hat issue*?
The Wolf
(*Of course, only the OP can decide if that is reasonable in the particular situation he experiences in his household. We’re just speaking in general terms.)