This article takes a focused look at all the women (and there were only 13 of them) recorded in London legal records for cross-dressing as men in the century after 1450. While this data set is too small to draw strong conclusions, the variation among the cases challenges our understanding of the purposes and motivations for female cross-dressing. The article provides a longer chronology of cross-dressing in London before 1603 from sources that include letters and courts overseen by the city, the Bishop’s commisssary, and the chancery.