Sharon Stone

In the latter half of the 1990s, Sharon Stone topped best-dressed lists not once, but twice for her unorthodox pairing of a casual Gap top with a designer skirt at the Oscars. Nearly 15 years have elapsed since then — years that saw Gap's fashion fizzle and its marketing lose relevance. But early signs indicate the brand may finally retake its position as the arbiter of casually cool, classically American style. That is, if it wins the next few weeks, which, while important for any retailer, will be particularly telling for Gap.