DY, it depends on what angle you are looking at it.
For example, a gang member would look at rival gang members wearing their colors as a negative and wearing their own as a positive. That doesn’t mean its a positive or negative association. It just means its an association.
If the father associates black hats negatively for whatever reason, then its not a positive. After all, its an external motion. There are way more important things to work on, whether or not bachur wants to associate as Yeshivish. He should make sure to brush up on his yinglish for instance 🙂