This thesis explores Black male experiences, perceptions, and representations of Black masculinities in contemporary society. The thesis considered how Black men of African Caribbean heritage navigate and negotiate their identities, relationships, and life trajectories through various social, cultural, and political challenges. The study used an ethnographic approach and various qualitative methods to gather and analyse the data. The data was drawn from twenty-four individuals and consisted of in-depth interviews and focus groups within a diverse group of Black men, ranging in age, occupation, education, and socio-economic status. The interviews aimed to delve into personal accounts of lived experiences, beliefs, and attitudes about Black masculinities and identities and the contributing factors to their perceptions and behaviours. The thesis outcomes included a deeper understanding of the complexity and diversity of Black masculinities and the challenges surrounding it. The thesis also provides insights into how Black men utilise various coping strategies and resilience in an attempt to combat discrimination, prejudice, and inequality and how they negotiate their identities in the process of these adversaries. The study's implications are significant, as they can inform policy and practice in various domains and contribute to the academic literature on masculinity, gender, and ‘race’ and the broader public discourse on social justice and equality. Overall, this thesis is an essential and timely contribution to understanding Black masculinities in contemporary society. Hopefully, this thesis is a starting point to inspire further research dialogue on this critical issue and promote greater awareness and empathy for the experiences and perspectives of Black men and the legacies seventy-five years after the Windrush generation came to Britain.