i hear both sides here about the way to dress. The truth is its not an easy situation for WOW, especially since the community will look down on anyone who doesnt copy the system. Of course the idea that we should all wear white and black is completely ridiculous and NOT a torahdika concept. We allow individuality in this religion…or at least were supposed to.
However before we attack WOW for saying she doesnt know if she can ever buy her son jeans, i think we need to take a step back and look at her from her perspective. We can talk about whats right and whats wrong, but HER reality is that her son and maybe even her family will be looked down upon if her son changes his style of clothing. This is not her or her sons fault, its solely the fault of the community placing their emphasis on the wrong areas.
WOW- this is your struggle right now, do NOT let your standing in your community dictate how your son should dress. The meaningless of the way he dresses is way beyond the emphasis placed on it. When i was in school they wanted to throw me out for having an untucked shirt!!! what kind of example is that setting, to this day i look at that rebbi and have negative thoughts. There is no reason in the world that your son should not dress the way he desires. Believe me your son knows it will make people in the community look down and him if he dresses and jeans, but hes probably smart enough to realize the stupidity of the issue.
For your sons sake, let him dress how he wants. Even though i know it must be very difficult for you, please dont make an issue of it as it shouldnt be an issue at all. Your sons happiness and success in life wont depend on white shirt vs t-shirt. But his happiness might depend on his parents supporting him through the thick and thin.