The discipline of dress history evolved from art history to become established in its own right over the last 40 years. Archaeological textiles have made valuable contributions to this study of historic clothing, especially for the early modern and medieval periods. However, textile finds from post-medieval or historical archaeology that intersect with non-excavated material cultures of dress in the eighteenth and nineteenth centuries are producing intriguing new directions for the study of both. At the Hyde Park Barracks, Sydney, finds of remains of blue and white striped cotton convict shirts and purple printed cotton female asylum clothing (c. 1820–1860) can be analysed through both archaeological and dress historical contexts. This essay explores what can be learnt about archaeological early Australian convict clothing from this interdisciplinary approach and is drawn from the rich PhD research opportunities among this material, provided by Professor Tim Murray.