Hypercharacterization (Lehmann 2005) or accretion (Kuteva 2008) is a widely attested cross-linguistic phenomenon which involves the accumulation of apparently “redundant” linguistic material in the marking of one category within the same structure. In this study I examine a number of cases of structural hypercharacterization in the history of English, focusing on the domain of syntax and paying attention to the motivations and functions of hypercharacterized forms and constructions. The selected case studies include the development of “strengthened” adverbial subordinators (e.g. for because, like as if), the occurrence of resumptive pronouns in subject extraction contexts, and the use of socalled “double-locative overlap constructions” and their relevance for the grammaticalization of existential there. These three examples show that hypercharacterization is interesting not only in and of itself, but also because of its great significance for language variation and language change.