Observation is a dynamic process important to our successful navigation of the world around us. It is not mere passive absorption of sensory input, but the ability to carefully attend to the richness, complexity, and interestingness of our daily experiences. This chapter suggests that engaging with the arts invites us to look more closely and intentionally, to notice patterns, to see nuance, and to seek the meaning of and in our observations. The chapter analyzes a plethora of empirical evidence across domains suggesting that observational and attentional skills can be developed through domain-specific arts training and may generalize beyond arts contexts. Trained artists, for example, often use distinct attentional strategies, exhibit greater attention flexibility and perceptual accuracy, and tend to process information more holistically than nonartists. Likewise, guided close-looking in visual arts contexts – whether in museums or classrooms – has been linked to improvements in clinical observational skills, diagnostic accuracy, and a willingness to engage with ambiguity. These capacities also underpin our abilities to experience empathy, to detect, interpret, and regulate our emotions, and to approach differences with curiosity, openness, and flexible thinking.