Guided by Self-Determination Theory, we offer an integrative and fine-grained analysis of teachers’ classroom motivating style (i.e., autonomy support, structure, control, and chaos) to resolve existing controversies in the literature, such as how these dimensions relate to each other and to educationally-important student and teacher outcomes. Six independent samples of secondary school teachers (N = 1332; Mage = 40.9 years) and their students (N = 1735, Mage = 14.6 years) read 12 ecologically valid vignettes to rate four dimensions of teachers’ motivating styles, using the Situation-in-School (SIS) questionnaire. Multidimensional scaling analyses of both the teacher and the student data indicated that motivating and demotivating teaching could best be graphically represented by a two-dimensional configuration that differed in terms of need support and directiveness. In addition, eight subareas (two subareas per each dimension of motivating style) were identified along a circumplex model: participative and attuning, guiding and clarifying, demanding and domineering, and abandoning and awaiting. Correlations between these eight subareas and a variety of construct validation and outcome variables (e.g., student motivation, teacher burnout) followed an ordered sinusoid pattern. The discussion focuses on the conceptual implications and practical advantages of adopting a circumplex approach and sketches a number of important future research directions.