From the 18th to the mid-20th century, there are records of many women who passed as men in order to live their lives in the way they wanted. For some women, the point was to be independent, do "men's work," and have men's privileges. For others, living as men allowed them to have married lives with other women unsuspected by the outside world. Many probably made the choice for a combination of these reasons. Passing women tended to come from the working class, in part because they did not have the opportunities for independence that education and money presented for middle-class and elite women, who could form partnerships with other women without passing as men.

In the 19th century, passing as a man was relatively easy, since women never wore pants or had short hair. These external markers were often enough to convince unsuspecting observers, and passing women were usually only detected if they became ill or had an accident, forcing them to go to a doctor. The practice did continue into the 20th century, however, the most famous example being jazz musician Billy Tipton, who had many girlfriends. There are so many records of passing women who were only revealed after death or under extraordinary circumstances, that one historian estimates that there must have been thousands of women in America over the years who passed as men and went undetected.