In the early 1980s, Kenneth Frampton encompassed Alexander Tzonis & Liane Lefaivre’s theorisations of critical regionalism in his attempt to address the crisis of modern architecture. Tzonis & Lefaivre had originally constructed critical regionalism around the architecture of Suzana & Dimitris Antonakakis. The two theorists traced a regional genealogy that combined Aris Konstantinidis’s “rationalist grids” with Dimitris Pikionis’s “topographically sensitive pathways” to inform the work of the Greek architectural couple. However, it was an outward-looking transcultural genealogy that historically sustained the two Antonakakis’ critical regionalism. Focusing on their architectural education at the National Technical University of Athens in the late 1950s, this paper draws out the elements that conditioned the Greek architects’ specific understanding of the regional in relation to the modern. While their strong biographical connection with Pikionis sustained his influence on their work, Konstantinidis’s impact on their architectural outlook was limited. Apart from Pikionis’s teaching, the conducive factors to their architectural formation lay in the theoretical lessons from Panayotis Michelis, the drawing and painting classes of Nikos Hadjikyriakos-Ghika, as well as the teaching of the former disciple of Mies van der Rohe, A. James Speyer. These cosmopolitan mentors enabled the two Antonakakis to rethink the regional in terms of the modern, in the way that rendered their work significant in the critical regionalist framework. The transcultural genealogy proposed here is therefore aligned both with the programmatic aims and principles of critical regionalism, and the two architects’ historical formation.