This picture (in the link below) just reminded me of an analogy Susan Faludi makes between headwear and maturity (in the excellent book Stiffed). Her point is that a cap is a sign of boyishness, and that prior to WWII, it was expected for men to eventually graduate to man-hat-wearing status. The fact that men no longer tend toward man-hats, and continue to wear caps pretty much until death, signifies an inability for contemporary men to, uh, grow up.

It's a pretty compelling argument in the context of the book. Read the book. Yeah, it's a thousand pages long, but it's really, really good.

Abramoff Plays Ball - Wonkette