A significant scientific and engineering challenge of recent years has been the fabrication of patterned polymeric and biomacromolecular brush nanostructures on surfaces. These structures provide researchers with a rich platform on which to exploit and observe nanoscale phenomena. In this review we present an overview of the field and highlight, through selected examples, recent advances in the nanostructuring of polymer and biomacromolecular brushes. This includes a brief overview of polymer brush synthesis techniques and how these are integrated with nanolithographic and templating approaches. We discuss the characterization of polymeric nanostructures and its associated difficulties, and we provide some perspective of how we see the future direction of the field evolving.