Action to reduce gender segregation in the male-dominated trades has been elevated in the past five years in Australia and other developed nations. However, there is little evidence to indicate that this has translated to a significant increase in female participation in the male-dominated trades. For example, the female composition of trades in the manufacturing, automotive, electro-technology and construction industries in Australia has remained stagnant at under 2%. This has consequences for the country’s economic growth and for the economic security of women. This study pursues two areas of inquiry: (1) it assesses the extent of the gender segregation of the trades over the past two decades in Australia; and (2) it explores the reasons why this gender segregation has been entrenched and what action can be taken to rectify the situation. In this research I adopt a critical social science methodology in which the process of social inquiry seeks to understand and challenge inequality in social and economic relations (Neuman, 2006, p. 95). I apply systems theory (Friedman & Allen, 2011; Ford & Lerner, 1992; Healy, 2014) as an organising framework to analyse the structural and individual level factors that contribute to gender segregation of the trades. Within this framework, I have also specifically examined three career development theories. These are: the meta-theory, Systems Theory Framework of Career Development (McMahon, 2014; McMahon, Patton & Watson, 2004; Patton & McMahon 2006); Social Cognitive Career Theory (Lent & Brown, 1996; Rogers & Creed, 2011) and Gottfredson’s theory of circumscription and compromise (Gottfredson, 1981, 2002). These three are selected as examples of career theories that provide significant insights into the external influences as well as the cognitive processes, such as self-efficacy and confidence, that impact on career decisions.