In this article, I explore the contingent and contested boundaries of looking good for young women in Vanuatu and the ways in which they negotiate these boundaries. I use women's dress as a lens through which to focus on the relationships among gender, modernity, race, and morality, and I show the ways in which all four are condensed and embodied in the moral and aesthetic imperative for women to look good. In particular, I focus on the island dress, a dress first introduced by missionaries but taken up after independence as an emblem of national pride and as the traditional dress for women. Although wearing the island dress is the commonsense way for women to look good, the young women with whom I conducted fieldwork in 2001-2002 and again in 2008 and 2011 experienced a great deal of ambivalence about the dress. They often preferred to wear trousers and T -shirts, which frequently won them the disapproval of their elders. By focusing on the polyvalent meanings of the island dress, the realities of young people's everyday lives in the capital, and the uneven terrain of the dress-scape of Vanuatu, I show that young women's love/hate relationship with island dress reflects their frustration with their ambiguous place in the contemporary national imaginary.