Street style has always existed but it has become a phenomenon of the 20th century. The increase in the standardization of life after World War II (Suburbanization, Mass marketing, the spread of television) may be linked to the appeal of "alternative" lifestyles for individuals in search of “identity”. Industrial production, particularly in the fashion sphere, was not only the popularization of stylists’ tastes that moved from high fashion to the peripheries of the system. These were also tastes that originated among economically disfavored, marginal groups, the whole range of metropolitan tribes, that can trigger new fashion production and diffusion processes.

Everyone is evaluated by their attire, and evaluation includes the consideration of colors, materials, silhouette, and how garments appear on the body. Garments identical in style and material also appear different depending on the wearer's body shape, or whether the garment has been washed, folded, mended, or is new.

Fashion is defined in several different ways, and its application can be sometimes unclear. Though the term fashion connotes difference, as in "the new fashions of the season", it can also connote sameness, for example, "the fashions of the 1960s", implying a general uniformity. Fashion can signify the latest trends, but may often reference fashions of a previous era, leading to the understanding of fashions from a different period re-appearing. While what is fashionable can be defined by a relatively insular, esteemed, and often rich aesthetic elite who make a look exclusive, such as fashion houses and haute couturiers, this 'look' is often designed by pulling references from subcultures and social groups who are not considered elite, and are thus excluded from making the distinction of what is fashion themselves.

Early Western travelers who visited India, Persia, Turkey, or China, would frequently remark on the absence of change in fashion in those countries. In 1609, the secretary of the Japanese shōgun bragged inaccurately to a Spanish visitor that Japanese clothing had not changed in over a thousand years. However, these conceptions of non-Western clothing undergoing little, if any, evolution is generally held to be untrue; for instance, there is considerable evidence in Ming China of rapidly changing fashions in Chinese clothing.

In imperial China, fashion, like in other cultures, was an indicator of the socioeconomic conditions of its population for Confucian scholars, however, changing fashion was oftentimes associated with the social disorder which was brought by rapid commercialization. Similar changes in clothing can be seen in Japanese clothing between the Genroku period and the later centuries of the Edo period (1603-1867), during which time clothing trends switched from flashy and expensive displays of wealth to subdued and subverted ones.

The beginning in Europe of continual and increasingly-rapid change in clothing styles can be fairly reliably dated to late medieval times. Historians, including James Laver and Fernand Braudel, date the start of Western fashion in clothing to the middle of the 14th century, though they tend to rely heavily on contemporary imagery, as illuminated manuscripts were not common before the 14th century. The most dramatic early change in fashion was a sudden drastic shortening and tightening of the male over-garment from calf-length to barely covering the buttocks, sometimes accompanied by stuffing in the chest to make it look bigger. This created the distinctive Western outline of a tailored top worn over leggings or trousers.

Phenomena of this kind have been studied for a long time in England and have revealed the importance of young people's street styles during the post-war period, which may be linked to the generation of baby boomers, who came to represent a new sociocultural category-the "teenager" who has money to spend and be an important motivation on the economic and cultural world.