During the tenure of Headmaster Rowan Algie (1984 – 1992), he introduced the concept of the Four Pillars – Academics, Culture, Sport and Service. While there is no doubt that Academics are the most important Pillar, he maintained that boys of Wynberg would only receive partial schooling if they did not embrace the concept of an holistic education.

Since this time, Wynberg boys have been expected to participate fully in activities of the four Pillars. The experiences gained in involving themselves fully in the life of the school would enable them to leave at the end of their five year tenure as well-rounded young men, suitably equipped to Make a Difference in their communities in the future.

Recognising the importance of an holistic education, pupils may work towards being awarded the most prestigious tie in the school – the Supera Moras tie. This is awarded at Silver and Gold level for those boys who have achieved at a high level in all four Pillars.