Its difficult to tell whether this was intentional or not:
If it was, then we guess that it was kinda funny, but it doesn’t quite work, because Will is actually posing in this photo, and without a hint of gurning self-awareness in that smile, it indicates that this was intentionally meant to be not funny. Which, in turn, makes it even more funny, because it looks like he borrowed Dennis Rodman’s church-goin’ clothes to his own basketball related comedy. So maybe it was intentionally a joke. Which makes it unfunny again.