The present dissertation examines the role of context-specific simulations in influencing the complexity of affective experiences, drawing on a constructivist approach to emotion. To link literatures on mental simulation and emotion, in Chapter 1 a connection is made through the grounded theories of cognition. Chapter 2 describes the development of a novel dataset consisting of context-dependent stimuli (i.e., 1,381 picture-word cues derived from 320 pictures-only stimuli) validated through online experiments (NExp1= 1,934; NExp2 = 403). Hence, an investigation of how contextual information influences the affective experience is illustrated, revealing that context more often enhances affective complexity by widening, rather than narrowing, the variation in the between-subject valence ratings. Chapter 3 employs a set of stimuli selected from Chapter 2 in a lab-based experiment in which participants (N = 30) rated affect intensity, and reported which emotions and bodily sensations experienced in response to generating both mental images and verbal thoughts. Mental imagery was found to enhance emotion complexity as reflected in the richness of the reports provided, with affect intensity and autobiographical recall accounting for the effect. Finally, in Chapter 4 the influence of mental imagery on emotion complexity will be studied across the imagery spectrum. To this end, in an online experiment participants (N = 72) completed measures of imagery vividness, alexithymia and gave written reports on how they feel when experiencing emotions at varying levels of valence and arousal, to obtain indexes on the complexity of emotion conceptualization. In line with the predominant literature, the more vivid the visual mental imagery of participants, the less alexithymia was reported, i.e., the less impaired is the process of emotion conceptualization. As highlighted in the final chapter (Chapter 5), overall the present dissertation contributes to deepening the study of the relationship between mental imagery and emotion. Assuming variation as inherent to emotion, consistently through different experimental designs, methods, languages and indexes, it is shown how context-specific simulations enrich the emotional sphere, by enhancing the complexity of affective experiences.