This paper presents a geographically large-scale, yet structurally fine-grained study on grammaticalisation in World Englishes. Attending to the relatively neglected domain of habitual aspect, we explore structural and areal patterns of innovation or conservatism regarding grammaticalisation and its synchronic reflexes in 13 varieties. Drawing on the International Corpus of English, we quantify usage profiles of the habitual auxiliary [use(d) to V], taking into account semantic, morphosyntactic and text-linguistic features. Properties of use(d) to are compared across varieties by means of a behavioural profile analysis employing hierarchical cluster analysis. The corpus results are mixed in that variation and cross-linguistic similarities do not seem to follow one single phylogenetic or areal trend but reveal more individual patterns, which can be partly explained by specific contact situations. The case study illustrates that one and the same synchronic grammatical variant may qualify both as a conservative relic and as an innovation as long as earlier colonial stages remain unknown. This leads us to problematise how, owing to the shortage of corresponding diachronic corpora, even instances of strongly directional types of change like grammaticalisation are open to different interpretations within competing narratives such as colonial lag, contact-induced change and the epicentre hypothesis.