This study examines the extent to which attitudinal dimensions associated with supervisor and officer styles explain subordinate officers’ satisfaction levels. Two frameworks, the average leadership style and person–supervisor fit, were employed and tested. To do so, survey data of 765 patrol officers and 146 patrol sergeants across five departments were used. The results provided little empirical support for the average leadership framework. After controlling for demographics and officer perceptions of work and organizational environments, sergeant style dimensions failed to exert a top-down effect on subordinate officer satisfaction. Support, however, was found for the person–supervisor fit framework. Specifically, when sergeant and officer views were congruent in the areas of support relations and expectations of aggressive enforcement, officers were more satisfied with their jobs. On the other hand, when sergeants viewed aggressive enforcement as important, but officers did not, officers were less satisfied. Finally, the patterning of results from a subsample analysis suggested that supervisory influences were more pronounced in the early stages of the officer–sergeant relationship. Practical implications associated with the person–supervisor fit framework are discussed.