Youth unemployment and underemployment are grave social issues prevalent in developing countries. Ensuring that youth attain productive ends or sustainable livelihood outcomes is a major concern of many governments, organisations and institutions globally. The purpose of the study was to determine the influence of enterprise strategy typologies on youth livelihood outcomes in Kamukunji Sub-County, Nairobi County, Kenya. Anchored on Department for International Development livelihoods framework and the General Systems Theory, the study applied a cross-sectional survey research design to gather data from 201 youth from registered youth groups. Analysis was conducted using descriptive frequencies and inferential statistics, namely Chi-square, Z statistic and Ordered Logistic Regression. Findings from inferential statistics established that regardless of the livelihood strategy typology youth adopted (business, wage employment, homemaking, arts & talents and agriculture-based), the livelihood outcomes did not differ significantly. As a group, livelihood strategy typology did not jointly determine youth livelihood outcomes. However, specific enterprise strategies whose parameters attained statistical significance were: wage employment (β = 0.74, p < 0.05) and arts/talent (β = 0.26, p < 0.05) which were important in predicting the level of YLO level. The study recommends that State and Non-State actors should implement elaborate and expansive business incubation and mentorship programs for youth. To improve livelihood outcomes for all youth, development agencies should ensure that youth-focused interventions target all typologies of enterprise strategies undertaken by the youth.