For the breakdancer, fashion is an important aspect of their identity. Many breakdancers in the 1980s dressed wearing flat-soled Adidas, Puma, or Fila shoes with thick, sometimes patterned laces. Some breakdancers matched their hats, shirts, and shoes to show uniformity within a breakdancing crew, and was perceived a threat to the competitor in the form of "strength in numbers." B-boys also wore nylon tracksuits which were functional as well as fashionable. The slick, low-friction surface allowed the breakdancer to slide on the floor much more readily than if she or he had been wearing a cotton shirt. Hooded nylon jackets allowed dancers to perform head spins and windmills with relative ease. Additionally, the popular image of the original breakdancer always involved a public performance on the street, accompanied by the essential boombox.
B-boys today dress differently from b-boys in the 80s, but one constant remains, and that is dressing "fresh". Due to the spread of b-boying as an artform from the inner cities out into the suburbs and to different social groups, different senses of "fresh" have arisen. Generally the rule that one's gear needs to match has remained from the 80s, along with a certain playfulness. Kangols are still worn by some, track pants and nylons still have their place combined with fresh sneakers and hats. Trucker hats were reintroduced on the scene in the late 1990s, well before the mainstream pop culture began wearing them again in numbers.
Function is heavily intertwined with b-boy fashion. Due to the demands on the feet in b-boying, b-boys look for shoes with low weight, good grip, and durability when given pressure to the sole as well as elsewhere. Headwear can facilitate movement with the head on the ground, especially headspins. Bandanas underneath headwear can protect from the discomfort of fabric pulling on hair. And wristbands placed along the arm can lower friction at a particular place as well as provide protection. Today's breakdancing styles which emphasize fast-paced, fluid floor moves and freezes, different from that of of two decades ago, requires more freedom of movement in the upper body, so less baggy upperwear is more common today (though pants remain baggy).
There are dancers and crews that now have begun to dress in a style similar to "goth" or punk rockers in order to stand out from the more traditional toned-down b-boy look.
Certain clothing brands have been associated with breaking. Tribal is an example. Puma is also well known in the breaking community. Both brands sponsor many b-boy events.
But aside from these generalities, many b-boys choose not to try too hard to dress for breaking, because in a certain sense one would want to be able to break anytime, anywhere, whatever the circumstances. This is related to why many would rather learn headspins without a helmet, despite it being able to facilitate. (back)