Chemical model systems provide valuable insights into biomolecular structure and interactions by allowing researchers to simplify, isolate, and manipulate aspects of the complex molecular machinery of living systems. This perspective describes my laboratory's design, synthesis, and study of chemical model systems that fold and self-assemble like proteins and elucidates the insights that have come from studying these systems. Many of these studies have focused on protein beta-sheets, which exhibit fascinating intra- and intermolecular interactions and play important roles in protein folding, aggregation, and molecular recognition.