Sign languages—the conventional languages of deaf communities—have been considered to provide a window into answering some questions regarding language emergence and evolution. In particular, iconicity, defined as the ‘existence of a structure-preserving mapping between mental models of linguistic form and meaning’, is generally regarded as a precursor to the arbitrary and segmental categorical structures found in spoken languages. However, iconic structures are omnipresent in sign languages at all levels of linguistic organization. Thus, there is a necessity for a more nuanced understanding of iconicity and its trajectory in language evolution. In this chapter, we outline different quantitative and qualitative methods to study iconicity and how one can operationalize them at lexical and discourse levels to investigate the role of iconicity in the evolution of sign languages.