Addressing the dearth of sociolinguistic variation research in the “new” varieties of English (D. Sharma, 2017b), this dissertation consists of a set of three sociophonetic studies on an urban dialect of Indian English. Relying upon community-based methods of data collection, this dissertation examines the vowels of an intergenerational sample of speakers from the upper-middle class neighbourhoods of Delhi. Each study of this compilation is guided by two principal goals. The first one is descriptive, that is to provide a detailed instrumental phonetic characterisation of the phonological vowels that compose the inventory of the variety. The second aim, which is historical, is to shed light of how Indian English carves its own diachronic trajectory, addressing issues relating to, for instance, diachronic stability and the transmission of language change across generations of speakers. Study I thus examines variation in the mid and low back rounded area of the vowel space, and seeks to draw relevant implications from the presence of lexical distributional “archaisms” (Wells, 1982, p. 626) in those vowels. Study II, on the other hand, is concerned with describing a chain-shift-like change in the short front vowels, and discusses the conditions of possibility for such change to occur in a mixed L1-L2 context. Lastly, Study III builds upon a complex allophonic “split” found and summarily described in Study II, and identifies this phenomenon as an element of historical convergence with geographically distant, unrelated, post-colonial varieties of English. Overall, several previously unreported features were found and described in detail in this dissertation, while important clarifications were also brought to areas that have been considered problematic in former descriptive works. Importantly, the studies also demonstrate that the variety under study and its patterns of variation seem to be, in general, amenable to the same kind of empirical analysis as other, so-called “native,” varieties of English, and call into question a number of ordinary assumptions on Indian English.