Her first job was as an assistant editor at Vogue, which she left to complete a Master's degree in art, also at Smith College.
Wanting to pay tribute to Starr, Penney, working with Nancy Smith, the executive editor of Self, created the first pink ribbon with the permission of SI Newhouse Jr., the owner of Condé Nast.
Having been employed by the magazine since 1989, Penney left Self in July 1994 to assume the position of director of new media development at Condé Nast Publications.
Clarkson Potter gave an advance of $75,000 for the book, its largest to that time, but wanted extensive changes after Penney delivered the initial manuscript.
[4] Penney wrote a series of posts on The Daily Beast titled "The Bag Lady Papers" starting in December 2008 in which she shared her experiences.