Around the late eighteenth century, makaʻāinana wāhine (female commoners) undressed before leaving Hawaiian shorelines to engage in a sex-for-goods trade with European sailors. As ships crisscrossed the Pacific Ocean, Hawai‘i became incorporated into a global trade network. Makaʻāinana wāhine were placed in direct contact with a growing number of seamen. These men sought the company of makaʻāinana wāhine who drew on male sexual desire to become the primary sellers of food and sex. These transactions granted makaʻāinana wāhine access to foreign trade and they became some of the primary possessors of coveted Western-style clothing. My reading of Hawaiian-language sources informs our understanding of the sex-for-goods trade as widely acceptable throughout Hawaiian society as evidenced by male family members accompanying women to ships. The 1820s brought about changes in the foreign population with multiple and competing interests in the sex-for-goods trade. Several Hawaiian chiefs and Euro-American merchants benefited from the sale of sex, food, and drink, even as opposition grew amongst other chiefs and Christian missionaries. These conflicting interests led to the sex-for-goods trade becoming a highly contentious topic. Around 1824, a chiefly decree prohibited the sale of sex. This prohibition was quickly retracted and, later, reinforced multiple times over the next two decades. Focusing on makaʻāinana wāhine in the analysis reveals that their social station was elevated by accruing and possessing Western-style dress. Hawaiian cultural knowledge reveals the adoption and adaption of Chinese silk dresses and European suits by the chiefs were deeply interwoven with displays of rank and rule. Therefore, these women purposefully undressed to accrual clothing that rivaled the chiefs’ attire. I argue, makaʻāinana wāhine’s adoption of Western clothing challenged chiefly authority and the multiple prohibitions were protracted efforts to stop women from accumulating clothing which elevated their social station within a shifting political, religious, and social order.