Bob Dylan cares deeply about fashionable headwear. Obviously. No, upon closer inspection it seems that quite the opposite is the case. It would appear that Bob Dylan is actually making fun of people who care too deeply about fashionable headgear. Dylan has got a track record of showing disdain towards the glamour scene. Glamour scene people are flighty and superficial, too caught up with their hats and ribbons and bows to notice the corruption around them. But Bob Dylan sees how the wind really blows, and he’s too cool to fall for any of it. According to himself. That position is, of course, its own kind of pretension. I suspect that Dylan probably had a lot invested in appearing to be too cool to care about appearing cool. At least in his anti-glamour-glamour phase of being a jerk-about-town in London and at The Factory and hanging out with all the coolest people and writing snarky songs about how not-cool the cool people were. It was later, when he got burned out with the scene, and started doing genuinely uncool things like living on a farm and finding Christ, that he was truly too cool to care.