- The core of gangster fashion stems from the dichotomy between poor beginnings and eventual wealth. A gangster is essentially a street criminal, someone who came from an impoverished background and gained money through violent and illegal means. "Working" gangster clothes thus often reflect hardscrabble origins: cheap fabrics and easily purchased materials. Wealthier gangsters, on the other hand, tend to flaunt their money through conspicuous consumption: expensive suits, gaudy jewelry and accessories that scream "I am loaded."
- The image of gangsters in the movies tends to have a huge impact on the perceived fashion of real-life gangsters. They see characters on the screen who reflect their "values" or struggles, and adopt clothing styles to match that image. The most noted example is the Al Pacino movie "Scarface," about a Cuban immigrant who rises to the top of the cocaine trade in the 1980s. Contemporary gangsters often cite him as an influence and adopt fashions intended to reflect the suits Pacino wore in the film.
- The classic gangster look arises from the fashion of the 1920s--exemplified by bootleggers like Al Capone and highlighted by famous movie gangsters played by James Cagney or Edward G. Robinson. It entailed a double-breasted, pin-striped suit, spats and a snap-brimmed fedora. The clothes stressed a sense of danger and menace, but also energy, reflecting the aggressive style that fit well with the popular image of organized crime.
- More modern gangsters (or "gangstas") closely follow contemporary fashion trends, marked by cultural bias towards black, Asian or Latino subcultures. The stereotype involves baggy clothes, particularly pants that sag down the wearer's thighs. This stems from prison jumpsuits which would often be issued several sizes too large. That trend seems to be vanishing, however, and is being replaced by more modern fashions. "Working" gangsters tend to favor khakis, button-down shirts and form-hugging workman's T-shirts. Gang affiliations can be noted through the color of the clothes, or from something simple like a bandanna slipped into a back pocket. Wealthier contemporary gangsters favor high-end suits by trendy designers. Conspicuous consumption remains a staple, however, and most contemporary gangster fashions involve a lot of "bling" such as gaudy necklaces, rings or watches.
- European gangsters, such as the Italian Camorra or the Russian mob, have acquired a stereotypical look of their own. It entails a white T-shirt and a track suit consisting of matching pants and jackets in primary colors. The omnipresent jewelry is often in evidence as well, as are sneakers or a similar sort of footwear.
