"permissiveness" is a really, really bad term in the context you are describing. Can you think of something better? "more open-minded"? "society embraces more...[fill in the blanks as suiting your purposes].... than two generations ago"?

Since your son leans towards outcasts, he may just be trying hats of minorities to see if they fit him. That, too, MAY pass.

Why do you have to tell your wife? Can you let the son confide in her as he chooses? Did the son authorize you to disclose this information to his mom?