This chapter explores the intersection of masculinity and financial behavior through a systematic review of literature guided by the Preferred Reporting Items for Systematic Reviews and Meta-Analyses (PRISMA) framework. It examines how traditional masculine norms, such as the need to provide, protect, and remain in control, shape men’s financial decision-making, risk-taking, and reluctance to seek advice. Drawing on Social Role Theory, bounded rationality, and Homophily Theory, this chapter identifies common behavioral biases among male investors, including overconfidence, loss aversion, mental accounting, and representativeness. These biases are often reinforced by cultural expectations and emotional pressures, particularly when men fall short of the internalized ideals of financial success. The chapter further explores how financial stress manifests itself in men and identifies resilience patterns, such as higher cognitive ability, psychological capital, and savings intentions that can buffer poor outcomes. It proposes practical gender-sensitive strategies for financial professionals, including behavioral coaching, goal-based investment planning, simplified investment products, and automated savings tools. The emphasis is on culturally informed financial advice, particularly in diverse societies, such as South Africa. By bridging behavioral finance with gender studies, this chapter contributes to a more nuanced understanding of male financial behavior and equips advisors, therapists, and educators with tools to promote financial resilience and well-being among men.