In the first few decades of the twentieth century, Hong Kong experienced major changes in the urban, societal, and political contexts. In the first few decades, the Chinese region was experiencing an age of reinterpretation of tradition towards new cultural and artistic productions. It was also during this time when the number of architects in Hong Kong more than doubled within a short span of several decades. Particularly when ideas of modernisation and Westernisation were being debated and critiqued in building a strong new Chinese nation, these architects were also engaged in experimentation of contemporary expressions and discourses in their architectural designs. This chapter will seek to question how these architects, focusing respectively on George Leopold Wilson (1880–1967) from architectural firm Palmer and Turner, and Kwan Wing-hong (1910–1973) from Davies Brooke and Gran, played crucial roles in the city’s modernisation from the 1930s until around the 1950s. The chapter will also uncover various faces of Chinese architectural modernity, including art deco, streamline moderne, and even explorations in critical regionalism and fill the gaps in Hong Kong’s architectural landscape of modernity in the first half of the twentieth century.