When my hashkafically intact son asked to wear colored shirts outside of Yeshiva (our oldest boy, no real precedence had been set yet)I reluctantly said yes,but when he asked for a gaming system I said no. I think it important to educate our children with an understanding of the difference between what is proper ben Torah behavior, and what is preferred ben Torah behavior. I personally think he will behave and be spoken to differently if he is in more formal wear, but I don’t believe wearing it against his will will accomplish that.
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