Raymond Driscoll was born in Haverhill, Massachusetts in 1915. According to newspaper clippings in his scrapbook, his early career included designing for the House of Worth in London. Returning to the United States, Driscoll opened a jewelry store in New York City around 1944, but it did not flourish. In 1945, Driscoll moved to Los Angeles where he lectured on fashion and jewelry at the Chouinard Art Institute and began to develop his own fanciful lines of clothing as well as outlandish couture pieces for special clients. Examples include gowns decorated with wine corks and diet pills. While in Los Angeles, Driscoll also served as the fashion editor for the Beverly Hills Bulletin.

In the mid-1940s, Driscoll adapted Eleanor Lambert’s popular best-dressed celebrity list into a scathing and witty “worst-dressed” celebrity list. He continued to update and revise the list at least through the mid-1950s. As intended, Driscoll’s worst-dressed lists attracted much attention and publicity. He also compiled his own best-dressed lists.

In 1950, Driscoll moved to Mexico City, where he became involved in the design and production of Mexican films. He also authored articles on fashion and style for Mexican newspapers. Driscoll opened a clothing store in Houston in 1955, and by 1957 he was back in New York designing loungewear for Kamore Robes.

Raymond Driscoll died on December 25, 2004. Little is known of the last four decades of his life.