This study aims to evaluate whether key factors related to homelessness and the utilisation of support services by homeless youth are associated with their employment outcomes. Data from 402 young people living in 21 housing accommodation buildings across three urban cities in England are used to evaluate the study's research aims. The results revealed that non-native and non-heterosexual homeless youth were overrepresented in housing accommodation and experienced lower employment rates compared to native and heterosexual homeless youth. The estimates indicated that employment levels among homeless youth were negatively associated with several factors related to homelessness, such as parental neglect, substance misuse, and inadequate social care during childhood. Conversely, the estimates showed that both employment levels and the duration of employment among homeless youth were positively associated with the use of well-being, educational, mentoring, and employment support services. A critical insight, however, indicated that discrimination in the labour market reduced their employment prospects. This study contributes to the literature by expanding the application of Capability Theory in the multidimensional study of youth homelessness. Furthermore, it develops and validates two new scales to capture both factors of youth homelessness and the utilisation of support services by homeless youth, facilitating evidence-based recommendations for policymakers. A policy approach should recognise the multifaceted nature of the challenges identified and advocate for a comprehensive strategy that integrates preventative measures, support services, and targeted interventions to address the root causes of homelessness while providing holistic support to vulnerable youth populations.