It moved through hoods, beanies and "Cat in the Hat" hats on to baseball caps first turned sideways and then with a flat brim (the polar opposite of the redneck and preppy artfully turned trend) and the current reinvented trend for "the bucket, " preferably from Louis Vuitton or Ralph Lauren.
WSJ: Tina Gaudoin on Style: The Hat Is On | The Top Winter Accessories