WoW: Are you sure your son thinks of it as a rejection? Or are you projecting that on him because that is how you would feel? Your line, “Oh, and you can wear anything you want (Ugh…)” is what bothered me the most. Because that sounded like your opinion on the clothing, and not what it means to your son. Maybe he just wants to be comfortable. It could be that to him the rejection of black and white is a rejection of Judaism. But it could be that it’s not. Don’t make the clothes a bigger deal than they have to be.
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