History and background of Guess. In 1981, GUESS? sold its very first pair of jeans to Bloomingdale's department store. Since then, GUESS? has grown, becoming one of today's most recognized and influential brand names. What began as a small, family-owned business is now a publicly traded, international organization. Currently, GUESS? operates over 180 retail and factory stores domestically, over 1,000 in-store shops