Unless one is a douche bag, I would say that guys who often wear their baseball cap backwards have sort of a chill, laid-back mentality —- “cool” and comfortable if you will.  (I sometimes wear my cap backwards hehe).

Keep in mind that there’s no activity that’s more lax/chill than well, laying down.

Sometimes I’ll be on a couch or my bed, while wearing a cap backwards.   I’ll forget that cap is on, and when I lie back, the brim of the hat first makes contact with the pillow, thus preventing me from getting into proper lay-down position.

I think there’s a reason it’s physically impossible to lay down while wearing a backwards cap…..

…nobody should ever really be that comfortable.