This chapter surveys specific examples of prosecutions for cross-dressing from the archival record. The examples show that although there were a wide variety of contexts in which the law could have been enforced, from those living transgender lives to feminist dress reformers to young people of both sexes cross-dressing for a night on the town, in fact arrests tended to be used tactically, following their underlying purposes. Two different categorical distinctions emerge that the law was trying to address: men versus women, and typical versus atypical gender identity.