Headwear has been a staple of hip-hop culture since its emergence in the 1970s; prior to becoming a component of the culture, hip-hop headwear comprised of traditional caps that were then adopted into the culture.

With strong ties to sport and culture, baseball caps made a transition from a staple of sport into casual wear and dress. Besides baseball caps, other components of headwear including bucket hats and beanies became reflectors of the culture through dress by "b boys," rappers and other artists. Since the 1990s, skateboard culture also influenced hip-hop (and vice versa). The recent popularity of five-panel hats and studded couture is also a reflection by outside influencers (i.e. high-fashion designers).

Headwear is a major component of hip-hop culture and has been influential in our visual understanding of urban dress.