I don't know where the idea got started that people look "cool" with their hats on backwards. I suppose some people with a literary bent might say that these guys are channeling Holden Caulfield. However, my response to that would be that if more than 1% of backward hat wearers know who Holden Caulfield is, I will be very surprised, so that arguement is bogus on it's face.
When I first became aware of the backward hat habit, the hats were on the heads of the acne prone teenage boys in our neighborhood at Fort Sill, OK in the mid-70's. Actually, while our neighbor kids were mostly white, the practice seems to have originated among the black kids who were, and are, invariably "cooler" than the white kids. It's the black kids, in my experience, who always seem to be on the leading edge of what is "hip" especially in the worlds of music, entertainment and style. Indeed, my perception of the situation then was that once the black kids saw that the white teenagers were copying their style, by wearing their hats backwards too, they, the black kids, wanting to re-establish themselves as the leaders in fashion, began wearing their hats SIDEWAYS!!! Then, when, in the fullness of time, the white kids adopted the sideways affectation too, the black kids went to the "upside down/inside out" option, closely followed by the "right side out but sideways and with the manufacturer's tag still attached up near the button by that little plastic line" look so that the tag flaps in the breeze and one diddy-bops down the street looking "very cool" indeed.
Anyway, my favorite story involving backwards hats was a scene I observed while watching an OU football game on TV during that same period. On this particular day, the game was being played in Norman, OK and it was a brightly sunlit afternoon. The stadium virtually glistened in the red and white livery of the home team. At one point a Sooners player made a breakaway run from scrimmage and as he headed for the goal line, the crowd was, instantly, on it's feet as one. As the camera panned the stands, there, in the cheering crowd, was a young man complete with his OU Jersey, his can of Coors in it's "koozey" and his hat turned fashionably backwards---AS, WITH HIS FREE HAND,HE SHADED HIS EYES AGAINST THE GLARE OF THE SUN---JUST SO HE COULD SEE !!!!! Apparently, nobody around him thought to say, "Hey Bozo, if you put your hat on the right way, you wouldn't have to do that." Indeed, a friend of mine recently showed me a still photograph of a scene almost identical to the one I described above with the backwards hat and the hand being used to shade the eyes. However my friend's picture had the advantage of a caption. It was entitled: "YOU CAN'T CURE STUPIDITY"