As the play makes clear, Moll's cross-dressing is the element of her character that perturbs the men in the play the most. As such, modern readers should have an understanding of how early modern English society approached dress, as well as why cross-dressing was a complicated phenomenon for the English theater in particular.
Generally speaking, early modern English children were dressed similarly in their early years, regardless of gender. Boys and girls alike would wear dresses and gowns until a specified time when the boys would be "breeched," or put into pants. Often, there was a breeching ceremony, making the shift a formal affair that marked boys' first transition out of childhood. While breeching did not necessarily happen at the same time for all English boys, it generally occurred between the ages of five and eight years old. This practice lasted well into the nineteenth century, with many arguing that it was still common in the early 1900s.
Thus, Moll's choice to wear breeches – rather than dresses or gowns – is not simply a sartorial one but also a declaration of her difference, her autonomy, and – for the more patriarchal characters in the play – her strangeness. This element of the play is complicated, however, by the fact that female roles on the early modern English stage were played by boys or young men. Thus, the Moll who appeared in original productions of the play would have likely been an adolescent boy, playing a woman, dressed as a man. This certainly would have added another layer of entertainment for the audience, but it also becomes a meta-theatrical commentary on the nature of the early modern stage and its relationship to society: while cross-dressing on the streets of London was considered taboo, the same phenomenon was widely accepted as common theatrical practice in the playhouses.
