This article explores how the reputations and agency of middling and plebeian women in sixteenth- and seventeenth-century London were affected by what they wore. Compared with provincial England, markets for women's clothes in the capital were more diverse and accessible. Ambiguous moral judgments were made of women based on their dress, but many sought to acquire good, fashionable attire as the right clothes would improve their options in terms of courtship, sociability and employment, as well as facilitating their ability to negotiate the metropolitan environment and providing them with a ready store of capital. Clothes were thus contested commodities which helped define the limits of the possible for women in early modern London.