This study is aimed at examining unconventional outdoor media advertising, the visualization structure of advertisements, and how messages are displayed. The research method used was Norman Fairclough’s critical discourse analysis, which involved the following: a) a text analysis, identifying the advertising visual structure; b) an analysis of discourse practices, which comprises how texts are narrated, modelled, produced and consumed; and c) a social practice analysis, which links advertising ideas and urban cultures. The research involved 30 respondents consisting of students, lecturers, and employees of Universitas Trisakti in a focus group discussion (FGD) to obtain public perceptions of visual attractiveness. Outdoor media advertising is attributed to the development of creative, short, readable messages, with simple visual structures that enable reading patterns from left to right or top to bottom. Based on observations of three research samples, it was found that there were novel ideas regarding outdoor media advertising creative strategies, namely, a) the novelty of advertising a new visual element structure by reversing outdoor media design principles; b) the intentional convention of reversed messages having evoked a more interacting public response; and c) advertising with sociocultural narrative content through the provision of advertised commercial products and services. The findings in this study show that there is a longer exposure level to unconventional outdoor media; therefore, the public’s goal is to interpret the message delivered. Unconventional advertising is the new orientation of communication strategies. The findings in this study have practical implications in arrangement of visual structures to become more interactive.