Abstract Stipules are generally regarded as the outgrowths of the leaf base in angiosperms. Other interpretations see stipules as independent organs comparable to leaves. Stipules have been recognized as an important trait for plant taxonomy and identification, and there has been great progress in the understanding of their morphology, development, origin, function, and gene regulation over time. Therefore, this review will briefly summarize past research and aims to clarify the occurrence, location, and morphology of stipules in the families recognized by APG IV and reconstruct their ancestral states. Additionally, the developmental morphology of different types of stipule is presented through scanning electron microcopy observations and a survey of the existing literature. The difference between stipules and ligules is discussed in relation to the occurrence of postgenitally or congenitally fused ‘continuous’ stipules. A distinction is made between ‘true’ stipules and ‘pseudostipules’. The origin of stipules at the base of the leaf is explained from different perspectives. About one-third of the families are reported to have stipules, mostly concentrated in the Rosid clade with the highest level of diversity. On the basis of the ancestral state reconstructions, stipules may be absent in the ancestors of angiosperms, but are present in the ancestor of Rosids, with a pair appearing on both sides of the petiole base. The transition between paired and annular stipules is discussed, the latter arising postgenitally or congenitally. Several hypotheses are discussed to explain the abundance of stipules in the Rosid clade and their limited presence in the Asterid clade.