The relation between goodness of organization (i.e., good Gestalt) and aesthetic appreciation is a long-lived one. Several important authors, including von Ehrenfels, Koffka, and Arnheim, mentioned and emphasized the importance and prominence of the relation between good Gestalt and aesthetic appreciation. However, a clear and nuanced understanding of what a ‘good’ experienced organization entails and how it relates to aesthetic appreciation is often missing in modern-day mentions of good Gestalt. Whereas some researchers argue for a direct one-on-one relation between the goodness of an experienced organization and its positive aesthetic appreciation, other researchers emphasize how an increase in organizational goodness (i.e., experiencing stronger organizational tendencies) may drive aesthetic appreciation. Although this debate is unresolved and requires further empirical investigation, we argue for a nuanced view encompassing both perspectives. Just like artists first need to acquire artistic conventions before they can meaningfully deviate from them, our perceptual systems first need a minimal reference system before they can welcome new levels of intricacy and complexity. On the other hand, increasing complexity can stimulate the development of new reference organizations and ultimately allow for a more organized perceptual world in the long term. In this presentation, we demonstrate how a nuanced understanding of the principles underlying perceptual organization can play a fundamental role in better understanding the principles underlying aesthetic appreciation. We will indicate how artists apply perceptual organizational tendencies of simplification and complication in their artistic practice, and how individual and contextual differences between art viewers can have a considerable influence on which organizations are positively aesthetically appreciated.