real-brisker…
It DOES make sense to ask DO you or WOULD you.
It may be that someone DOES not wear (or even own) jeans right now, because he is away at yeshiva or in other circumstances where he can NOT wear them. However if and when he will be in different circumstances (next summer, next year, or whenever) then SOMETIMES (obviously not constantly) he WILL wear jeans.
So, when YOU say the question SHOULD be “DO you wear jeans?” the answer to that question would NOT necessarily reflect one’s attitude about wearing them, it would ONLY answer if one wears them NOW (in their present matzav). To know IF one WOULD wear them, if/when they will be in a different matzav, which IS the question that needs to be asked if we are trying to find out if people think there is anything INHERENTLY wrong with it, you DO have to ask (not only DO YOU, but also) WOULD YOU?