It connoted something like 'I'm a little cooler than you.
It's a way to personalize your look, to stand out while also maintaining your position in the crowd.
It's one of those masculine paradigms - the pirate - like the cowboy and the all-American prep, that crops up from time to time in men's fashion. They do get kind of recycled.
People are finally catching on. It's a chic look that's really practical. It allows for different temperatures. You can take the hat off, take the scarf off. On warm days you can just turn your collar up.
