The first American to win an Olympic medal in downhill skiing, Pitou took home two silver medals at the 1960 Olympic Games. As a high school freshman, Pitou ignored the 'no girls allowed' policy for the school's skiing team, hiding her hair under her helmet and going by the name 'Tommy'. Pitou made the boys' team, competing in several races until her helmet flew off in a crash, blowing her cover. Pitou continued to train, making the U.S. Olympics Ski Team at 17 and being mentored by fellow American Andrea Mead Lawrence. Following her skiing career, Pitou worked as a fashion consultant in the ski industry and established training schools in New England. Hilary Clinton has credited Pitou with teaching her to ski. Today, Pitou's eponymous travel agency, Penny Pitou Travel, leads skiing expeditions and tours throughout Europe.