This chapter focuses on the role of shaded walkways and greenery in defining what is meant by tropicality. Theories of ideas concerning tropicality in urban design and city spaces are a recent attempt towards defining elements of urbanism characterised by the elements of a tropical region. It is put forth that both shaded walkways and greenery have a key role in constituting cultural tropes in defining a regional version of universal ideas and frameworks of tropicality. The two tropes are the role of the shaded walkway and the greenery. The absence of urbanist histories and past models underscores the difficulties and dilemmas in outlining locally derived positions including conceptualising the urbanist and spatial organisation of new cities.