Transgender History takes a chronological approach to the subject of transgender history, with each chapter covering major movements, writings, and events from the mid-twentieth century to today. Chapter 1 covers the transsexual and transvestite communities in the years following World War II. Chapter 2 addresses trans radicalism and social change, which spanned from 1966 with the publication of The Transsexual Phenomenon, and lasted through the early 1970s. Chapter 3 focuses on the mid-'70s to 1990—the era of identity politics and the changes witnessed in trans circles through these years. Chapters 4 and 5 are broken into the gender issues witnessed through the '90s and '00s, respectively.

Included are helpful sidebars that highlight quotes from major texts and speeches in transgender history and feature brief biographies of key players, plus excerpts of first-person narratives from transgender memoirs and discussions about treatments of transgenderism in popular culture.