Before J.Crew had Joan Smalls, Hilary Rhoda or Arizona Muse, they had Dawson's Creek. Sure enough, the Fall 1998 catalog features the baby-faced cast cavorting around some picturesque, East Coast landscape in simple (albeit nondescript) casuals. But Dawson and Pacey are only the tip of the very preppy iceberg: the '80s and '90s archives of the brand's now ubiquitous style guides show Rebecca Romijn, Patrick Dempsey and Lauren Hutton exercising their right to normcore before the concept spurred any kind of public outcry. And who would have guessed that this trove of roomy chinos, classic button-downs and expertly cut one-piece bathing suits would eventually lead to Jenna Lyon's current foray into bejeweled baseball caps and vividly colored jacquard pants? Either way, we're not complaining.

—Emily Ferber