If the Gap was the Cinderella among clothing retailers in the affluent 1980s, its downmarket offshoot Old Navy enjoyed a comparable fairy tale existence in the belt-tightened 1990s. The brainchild of Gap CEO Millard "Mickey" Drexler, the store began as an attempt to reel in customers put off by the Gap's prices but too hip to buy clothes at Wal-Mart. By relying on attractive packaging, quirky promotions, and the pioneering use of headsets by customer service personnel, Old Navy succeeded in making cheap threads seem cool. Even the Gap's pseudo hipsters were won over by a series of campy television commercials featuring such entertainment industry fossils as Barbara Eden and Eartha Kitt, alongside an adorable pooch named Magic and the campaign's icon, weirdly fascinating fashion doyenne Carrie Donovan.

Further Reading:

Caminiti, Susan. "Will Old Navy Fill the Gap?" Fortune. March18, 1996.

Kaufman, Leslie. "Downscale Moves Up." Newsweek. July 27, 1998.