This article explores how entrepreneurs’ clothes can influence investor assessments. We theorize that, although clothes are very unreliable indicators of underlying venture quality, they are predic-tive of fundraising performance such that informally dressed entrepreneurs tend to outperform formally dressed entrepreneurs. Moreover, we propose that clothes can create sufficiently strong first impressions to make investors neglect later, more important signals like prior entrepreneurial experience. Two field studies, an experiment, and a series of interviews support our hypotheses. Our article contributes to research on impression management in entrepreneurship by outlining the benefits of casual clothes, as well as showing that they can have lasting effects. Moreover, it con-tributes to signaling theory by illustrating how initial contextual factors can diminish the relevance of later strong signals.