The evolution of branching was pivotal to the diversification of plant architecture, providing ways to colonize the environment and optimize resource acquisition both above and below ground. Fossil and phylogenetic evidence indicates that branching evolved independently in the two generations of the land plant life cycle. In this chapter, I focus on shoot systems and discuss two contrasting patterns, occurring at different levels: conservation and diversity. I show that two similar branching modes, terminal and lateral, are found across extant and extinct land plant lineages. Despite conservation of gross morphology, branching morphogenesis is highly disparate at the cellular level and is orchestrated in various manners between and within lineages. In contrast, the molecular mechanisms underpinning branch development could be largely shared among land plants.