I don't know that the dress code post is indicative of society in general or anything. Probably just an isolated incident. Boys that age will often try to get by with obscene content on shirts, and occasionally they will slip one past that the administration either doesn't understand (maybe no one ever swallowed for the principal?) or simply doesn't see (the text is on his back, when he walks into a classroom, there's probably a backpack or hoodie hiding it, and when he's in class, there's a chair back behind him).

In my opinion, both clothing items are distasteful. Those shorts are not appropriate for school. While the boy's is an obvious cry for attention and back-patting from his peers, he is at least not exposing body parts.