Getting dressed is a ubiquitous and essential component of being human. Each day, our selection of clothes offers the opportunity for an agentic curation and expression of self. Research indicates how the body’s adornment influences how we feel and experience life. As positive psychology explores what makes life most worth living and seeks to promote well-being actively, the daily act of dressing emerges as a potent way to support this pursuit. Building on the age-old adage, ‘look good, feel good,’ this paper examines how articulating self through personal style aligns with the broaden-and-build theory, self-determination theory, and other positive psychology concepts to enhance well-being and contribute to the good life. This exploration aims to bridge the gap between theoretical concepts and practical everyday actions, highlighting how intentional dressing can catalyze individual and collective well-being.