Since the late 19th century, there had been a presence of criminal gangs in American cities, mostly involved in low-scale extortion and loan sharking activities. Prior to the Prohibition Era, most organized crime schemes were run by corrupt politicians, employing gangs to intimidate opposition candidates in return for disregarding illegal gambling and prostitution rings. Yet, these power dynamics would dramatically shift with the Prohibition Era of the 1920s, a period where the outlawing of alcohol led to a subsequent rise in organized crime. Initially, street gangs began with protecting illegal breweries and other alcohol-running operations from rival gangs and providing security for speakeasies. As mobsters began accumulating excessive amounts of money, they also started hiring lawyers and accountants to launder money, as well as paying off cops and politicians to turn a blind eye to their activities. With the business opportunity of illegal booze and the growth of organized crime, strategic partnerships between gangs became more common. Thus, as gangsters grew in power, influence, and numbers, their attire began to reflect both their defiance and status. Hence, the infamous gangster suit was born. Made of expensive, sought-after fabrics such as wool and silk, each suit was exactly tailored to the mobster it represented. This style was based on a demonstration of bravado to impress associates or intimidate rivals. For instance, the use of pinstripes made figures appear taller and more imposing, whereas fedoras and other accessories added an overall sense of style and sophistication. 

Hollywood also played a crucial role in establishing the gangster aesthetic as a cultural phenomenon. Beginning in the 1930’s, movies such as Little Caesar (1931) and The Public Enemy (1931) romanticized violence and crime, introducing audiences to the sharply dressed gangsters of cinema. Most notably, Paul Muni’s role as Tony Camonte in the 1932 Scarface, dressed in an iconic pinstripe suit topped with a fedora, quickly became the face of the gangster genre. As the decades progressed, filmmakers used the gangster suit to reflect both a piece-de-resistance fashion trend and a character's evolution. 

As organized crime evolved throughout the decades, so did its fashion. For instance, The Godfather Part II (1974), depicts two timelines: one of young immigrant Vito Corleone’s introduction to a life of crime in 1917, and the struggles of Michael Corleone in the 1950s. As the film jumps between the two periods, the suits contrast between the dull-colored pinstripes of the early-1920s and the summer style of Michael Corleone’s Havana suit. Yet, this film not only illustrates personal evolution, but the shifting image of crime as well. More specifically, while Vito’s timeline exhibited the early beginnings of crime culture, Michael’s era displayed a period of post-war economic boom with a much flashier aesthetic. 

As gangster attire evolved with the decades, the 1950s represents one of the most pivotal transformations, reflecting the era’s economic boom and cultural shifts. This decade was defined by a show of opulence, witnessing the gangster aesthetic drawing influence from the zoot suit, which originated in African American and Latino communities. This style took on a more flamboyant and baggy look in contrast to the muted tones of previous decades. In particular, Goodfellas (1990), based on Nicholas Pileggi’s biography of real-life gangster Henry Hill, most distinctly portrays several decades of the gangster aesthetic’s evolution from 1955 to the 1980s. For this film, director Martin Scorsese played a major role in the costume design and development. Having supposedly grown up around many “wiseguys” in Little Italy, Manhattan, Scorsese based the outfits in Goodfellas on his own memory of real-life gangsters. Most distinctively, he placed heavy emphasis on the capo collar, which was elongated to usually four inches long, rounded or spear-pointed, and lacking in tie space. Even in more recent American gangster films, such as 2019’s The Irishman, these collars were often used to indicate who was a “made” man of an organized crime family. 

During the film’s 1950s timeline, Scorsese flaunts characters dressed in colorful silk suits, camp shirts, and knit sweaters, all topped with excessive jewelry. Moving into the 1960s, the popularized leather jacket played a major role in influencing the decade’s style. In the scene where Henry Hill, played by Ray Liotta, furiously storms out of his car, he is dressed in a distinctive brown leather blazer and a .38 tucked into his waistband. By the 1970s, the Lucchese crime family’s wardrobe evolved to include leather, oversized collars, and more casual wear, mirroring disco-era fashion trends. Scenes taking place in the 1970s often feature wiseguys dressed in sports jackets with open collars as opposed to their previously worn suits. Particularly in the prison scene, Henry Hill is seen wearing an Adidas navy tracksuit, a style heavily popularized after the 1972 Olympic games. This shift may be attributed to the rising prominence of sports culture and the changing nature of crime, shifting deeper into narcotics and street violence. 

A symbol of individuality and nonconformity, the gangster suit continues to inspire modern designers and popular culture. For instance, Yves Saint Laurent’s groundbreaking Le Smoking, a tuxedo designed for women, first made its appearance in 1966, rebelling against strict gender norms. As part of his Pop Art collection, this specific piece praises the classic silk-lapelled smoking jacket, with adjustments made catering to women, such as the sleeker collar and a tapered waist. More recent designers have also incorporated elements of the mafia aesthetic into their collections, introducing modern interpretations of the classic gangster suit. In Spectre (2015), Daniel Craig’s James Bond wears a black three-piece suit to the funeral of a gangster. This particular outfit was developed from Tom Ford’s “Windsor” model and entails classic-inspired details to blend in with that of flashing gangsters from the past. For example, the waistcoat, with four welted pockets, takes inspiration from the three-piece suits donned by many gangsters between the 1930s and 1940s. Furthermore, The Wolf of Wall Street from 2013 features several Giorgio Armani suits, worn by Leonardo DiCaprio as Jordan Belfort, paying homage to earlier crime bosses with the pinstripe and double-breasted style of the 1920s and 1930s gangster aesthetic. 

Yet, while the gangster suit serves as a reminder that style can represent both story and status, it does receive criticisms for romanticizing criminal activities. Throughout history, fashion has been used as a symbol of rebellion, but when applied to organized crime it creates an allure that often overshadows the violent reality of such professions. Films and fashion, producers and designers have all contributed to establishing the mobster aesthetic as one of resilience, self-made success, and noncompliance to societal norms. However, this makes the distinction between admiration for style and the glorification of crime blurred and vague. Thus, does the gangster suit represent power and individuality, or does it mask the harsh realities of the world from which it originates. Ultimately, the legacy of the gangster suit lies not in its sharp tailoring or iconic pinstripes, but in its ability to provoke discussion on the crossroads of style, status, and morality.