The Singapore government promulgated the Retirement and Re-employment Act in 2012 to promote extending working life. This article offers insight into the utility of Bourdieu’s conceptual framework of habitus, field and capital in exploring how older employees in Singapore adjust to re-employment. Semi-structured in-depth interviews were conducted with 10 re-employed older persons consisting of four women and six men. The thematic analysis of the data indicated that a series of adjustment strategies underpinned by the realism-, positivity-, productivity- and proactivity-oriented habitus synergized to empower research participants to navigate through the field of re-employment. The article proposes that in the Singapore context policy makers and employers need to take a habitus-sensitive approach to re-employed older persons, developing a habitus-friendly field of re-employment.