The plant lipid polymers cutin and suberin play a critical role in many aspects of plant growth, development, and physiology. The mechanisms of cutin and suberin biosynthesis are relatively well understood thanks to just over 2 decades of work with primarily Arabidopsis (Arabidopsis thaliana) mutants. Recent advances in our understanding of cutin and suberin structure have arisen through the application of novel chemistries targeted at quantitative comprehension of intermolecular linkages, isolating intact suberins and cutins, and the application of advanced analytical techniques. The advent of high-throughput transcription factor binding assays and next-generation sequencing has facilitated the discovery of numerous cutin and suberin-regulating transcription factors and their gene promoter targets. Herein we provide an overview of aspects of cutin and suberin structure, biosynthesis, and transcriptional regulation of their synthesis highlighting recent developments in our understanding of these facets of cutin and suberin biology. We further identify outstanding questions in these respective areas and provide perspectives on how to advance the field to address these questions.