This chapter re-examines the vicissitudes of fashionableness of Nehru and Mao jackets in the 1960s-1970s West. The fashion dynamics of these jackets without lapels and featuring standing or high turn-down military-style collars calls for renewed investigation and a comparative analysis. Although scholarship of their Sino/Indic style antecedents is well developed, misperceptions as to sources and impulses behind their vogue (such as the Beatles’ having made the Nehru jacket popular following their trips to India in 1966/1968 or its having originated with a single celebrity designer like Cassini – or was it Féruch or Cardin?) stand in need of revision. Preliminary probing suggests some initial Nehru- and Mao-jacket awareness via mass circulation journals such as ‘National Geographic’ and ‘Life’. Also noted are stereotype references to the mystique of India and threat of China found in for instance James Bond films and the 1964-65 TV series ‘Jonny Quest’, and going back to ‘Fu Manchu’ yellow peril novels and cinema, and an austere, disciplined, quasi-martial silhouette that lends itself to the generic attire of masterminds and super-villains. How do all these aspects relate to one another? Everything suggests the initially ‘cool’ as opposed to later ‘un-cool’ (and the still later ‘re-cool’) connotations of these jackets have had little to do with their intrinsic qualities as apparel.