This paper explores Illogical Classification-Based Thinking (ICBT) and its role in forming Positive, Negative, and Neutral Associations. Building on established theories such as the Halo and Horns Effects, and introducing Neutral Associations, this research examines how impressions lead to the automatic grouping of traits based on impressionistic judgments rather than logical reasoning. Using AI-generated images and a diverse participant pool, two studies were conducted: Study 1 confirmed the reliability of attractiveness categorizations, while Study 2 tested hypotheses related to trait associations. Results indicated that initial impressions significantly influence trait grouping across positive, negative, and neutral contexts, supporting the presence of ICBT. The integration of Kahneman's dual-process theory provided a comprehensive framework for understanding the cognitive processes involved. Findings have broad implications for social psychology, decision-making, consumer behavior, and organizational behavior, offering insights into how stereotypes and labeling are formed. Despite limitations such as sample representativeness and potential gender bias, this research contributes to a deeper understanding of impression-based judgments and cognitive categorization processes.