In recent years, wisdom is seen as a key resource for school leaders in dealing with the dynamics of the changing school environments. This study purports to expand the growing interest on wisdom by testing a model that describes the impact of transformational, visionary, charismatic and ethical leadership styles on wise leadership development among a select group of 320 Filipino secondary school principals through structural equation modeling. A multi-aspect questionnaire was used to characterize the respondent principals' leadership orientation and styles. Specifically, the following adapted tools were used: the Transformational Leadership Behavior Inventory, the Ethical Leadership Scale, the Charismatic Leadership Scale, the Visionary Leadership Scale and the Wisdom Development Scale. Results of the structural equation model revealed that: (1) each of the four types of leadership has a significant positive impact on wise leadership development, (2) high charismatic qualities of principals could lead to higher capability for wise leadership, (3) transformational and visionary leadership appeared to have the most impact on wise leadership development and (4) five pairs of leadership styles (visionary and charismatic, charismatic and ethical, transformational and ethical, transformational and visionary, and transformational and charismatic) when any of them is practiced by the school principals indicate stronger effect on wise leadership. Implications for practice, theory and policy are also discussed in this paper.