The contemporary debates about crime and criminalisation in the Anglophone Caribbean are centred on serious or major crimes. The body of laws that govern minor offences and vagrancy that have been very durable and are applied to police the poor and socially excluded have received little attention. Yet these broadly and vaguely worded colonial criminal laws have become indispensable in constructing gender non-conforming and transgressive persons as modern vagrants in the Caribbean. This article explores the history and persistence of vagrancy legislation and their current use in policing gendered bodies that are “out of place” and “out of order”.