The monophthongization of the diphthong [ai] to [a] is possibly the most stereotyped feature of Southern American English. This feature can be observed to varying degrees across the American South. Although monophthongization represents an important social symbol in the South, its pervasiveness has begun to recede in recent generations. This sound change has been brought on by multiple factors including population mobility, education, and urbanization, which have promoted acceptance of a more standardized variety of American English, including diphthongal realizations of [ai]. The current study examines the change in progress toward [ai] in 20 children aged 8–10 from western North Carolina in three different speaking styles: citation-form words, read sentences, and informal, unscripted talks. In addition to acoustic analysis, stylistic variation was evaluated by 20 central Ohio listeners (10 males and 10 females). Participants were asked to listen to individual words and to rate the degree of perceived monophthongization on a seven-point scale. Results showed an increase in perceived monophthongization from citation forms to informal talks. Compared to girls, boys had a higher occurrence of the monophthongal variants and lower occurrence of the full diphthongs across all production types. Discussion will focus on the advancement of the sound change.