Polymer brushes have been theoretically described, their behavior under diverse conditions has been modeled, and their preparation via surface-initiated polymerizations (SIPs) has been progressively refined. However, despite three decades of research endeavors by chemists and materials scientists, an array of challenges and questions characterizing the synthesis, characterization, and understating of polymer brushes remains and motivates this Perspective. How do the main structural parameters of polymer brushes link to their unique properties? Can we synthesize multifunctional brushes in a more practical and scalable manner? Can we successfully overcome the intrinsic challenges that enable their comprehensive characterization? While being closer than ever to the translation of polymer brushes into technologically relevant materials, we have tried to answer these questions by simultaneously outlining the status of research in this subfield of polymer science and the evolving perspectives in their synthesis and characterization.