This essay traces how multicultural Singapore attempts to construct its fashion identity in the broader context of the global fashion conversation from 1960 to today. Within 52 years of independence, it has become the epitome of modernisation in terms of rapid capitalisation and industrialisation, to earn the title of most expensive city for expatriates to live in for the fourth consecutive year. Despite its first world economy status, its fashion identity, to which its national identity is attached, does not enjoy a similar stability. This essay creates a dialogue between the representations of Singapore in Singaporean fashion media and in Vogue US, to show how semblances of Singaporean fashion identity are interdependently formulated within this network. These reveal the larger processes of globalisation, hybridsation and (re)indeginisation that manifest in Singaporean dress.