This chapter explores the cultural forms, contexts, and meanings of cross-dressing in the years leading up to its criminalization. A wide range of cross-dressing practices occurred during these years, shaped by the multinational, predominantly male migrations of the gold rush and the U.S. annexation of California from Mexico. These events shaped the meanings, pleasures, and anxieties that attached to cross-dressing practices, some triggering considerable gender and racial apprehension and others supporting the growing regional dominance of European American men with remarkable ease. Despite their disparate cultural meanings, these cross-dressing practices were legal equivalents, unhampered by government interference in a heterogeneous public sphere. This virtual legal vacuum was short-lived, however, and as the gold rush years came to a close, San Francisco’s government passed a local law that criminalized public cross-dressing, marking a new approach to managing gender in the rapidly developing city.