If you trace the roots of the reverse baseball cap it originated as a street fashion statement of poor, urban, black Americans, around the time that breakdancing first took off. It also had connotations of gang membership if worn in a certain manner. A reverse or sideways cap also started to show up in hip hop and rap music videos in the 1980's, which added to the urban cool factor. Pretty soon, young white males who were seeking approval from their peers adopted the fashion and hoped that some of the urban cool would rub off on them. All this was many years ago but the fashion still lingers. It has taken on different connotations now, more as the uniform of the party dude these days.

It's more to do with young men of a certain age group and their maturity level, rather than a devolution of all men. Well made suits and uniforms are still outer displays of male success and power, although I tend to think high level sports uniforms would be more desirable than military uniforms to a woman seeking a mate these days.