A few years ago, my nonagenarian grandfather drove himself to Urban Outfitters and bought one of his grandsons a present of a wool cap, the kind of tweed thingie that Bobbie Jones' caddie at St. Andrews probably wore. When unwrapping the package, my son pretended to be enthusiastic about wearing his grandfather's fashion choice, until he saw it, and decided it was cool. He wore it everyday (and I started seeing pictures in the press of Brad Pitt wearing an identical one). But then February arrived and it got too warm for hipster clothes.
Basically, Daniel Patrick Moynihan's Rule of Proximity to the Canadian Border applies.