There is nothing intrinsecally wrong with wearing jeans and blue shirts in a black-and-white community, in fact it may open the path to a more relaxed and accepting atmosphere, BUT, it takes A LOT of guts and enormous strength to do that, especially for a teenager. No doubt if he has been somehow bullied etc. with black-and-white clothing already, if he is seen around with jeans and a laptop is going to get much worse, with rebbeim and teachers and everything, the neighbours, etc etc. Who can withstand such pressure? Some can, but not many. Can this boy? I am not certain, in fact, I doubt.
He seems to be intending to “test the waters” but he will create much more trouble for himself, an amount of trouble I am not sure he has fully evaluated, to the point that (I don’t condone, but unfortunately, it is plausible reality) he might be pushed away, and possibly, worse than checking out a bunch of stupid things on the internet. We can only hope that, leaving him space, he will feel self-confident enough to build himself some outlet (and possibly wear jeans elsewhere, say at college?) while avoiding to stand out too much in your environment, and yet, defending how he stands out from the “average” or “norm” or “community standard” which people must feel he does because he has good reasons to. The third part, you in the family and everyone else who cares for him, should participate in doing. However, the first step for that, is for him to be convinced he does because he has good reasons to. I am not sure this is the case now, in fact he may at this time have the wrong reasons, and there, you and his father need to help.