The Dapper Fashions of Rude Boys


Before she was the business mogul that we recognize today, Rihanna spent the mid-Aughts singing tunes as an international pop star. Among her collection of hits was the 2005 dancehall number, “Rude Boy.” 

“Come here rude boy,” Rihanna demands in her signature mezzo-soprano as a ragga beat thumps along. Who is this songstress summoning? To some ears, she’s calling for a guy with a displeasing manner, but for others, she’s referring to a Jamaican fashion icon. 

A Rude Boy (“bwoy” in Jamaican Patois) is a fifty-year-old cultural figure who challenged stereotypes through dapper fashion. Although a Rude Boy today can be spotted on the streets of London or in the clubs in Singapore, the first Rude Boys are traced to a group of young men from the shanties of Kingston, Jamaica. 

The Rude Boy emerged after Jamaica attained independence from a more than two centuries-long British rule. Before the 146-mile island was a colony, it was the homeland of the Taino. But after Christopher Columbus’ ships arrived near its shores, the Caribbean island was forced to centuries of Spanish and, later English, colonized rule. 

Colonization brought slavery to the island, forcing Tainos and later hundreds of thousands of Africans to migrate and work in the sugar and cotton industries. Slavery lasted for three centuries until it was made illegal in 1832. Political and societal inequality towards Afro-Jamaicans continued under British governance until 1962, the year Jamaica became an independent nation.  

As Jamaica entered a new era with hope and optimism, the racist legacy of colonial rule presented itself in the high unemployment of poor, young Afro-Jamaican men. The lack of opportunities for both economic and personal growth led some men to join gangs and partake in criminal activities. Due to their already low status in Jamaican society, the actions of these few spoke for a whole generation.

Amidst these social and economic pressures, the Rude Boy emerged. McMillan described their uniform as “white breast-pocket handkerchiefs, polished brogue shoes, white starched shirts with throat-strangling ties, and topped by trilby hats that they set at a cocked angle.” 

By appearing in these dapper and refined fashions, Rude Boys challenged the social status they were given. Historian Monica Miller stated that Rude Boys were “stylin’ out to subvert racial order, perform their identities far from a lost homeland, and redefine Blackness and cosmopolitanism.” 

These sartorial statements were inspired by the media that the Rude Boys consumed. They enjoyed American Westerns and gangster films, listened to jazz, and admired English dandy fashion. “The rude boy culture came to define an ethos of self-worth, determination and creativity,” said Jean-Philippe de Dieu, “… ready to strike back at a conservative and racist society.”

Aside from the streets of Kingston, the Rude Boy look outfitted singers of then-upcoming music genres ska, rocksteady, and dancehall. It was the preferred style for perhaps the most well-known Rude Boy of the mid to late twentieth century, Desmond Dekker. 

Hailing from Kingston, Dekker worked as a welder before finding success as a singer. It was as a welder that he met Bob Marley, and through this friendship, Dekker began his singing career. Dekker found opportunity as a back-up singer and then as the lead in the group Desmond Dekker and The Aces. It was through this group that his 1968 song, “Israelites,” became an international hit and sky-rocketed Dekker’s career. 

“After a storm, there must be a calm / They catch me in the farm / You sound your alarm / Poor me / Israelites,” Dekker sang while wearing slim suits, bow ties, and white ruffled shirts. When performing his other hits, “007 (Shantytown)” and “It Miek,”  he personified the fashionable Rude Boy with Modish shawl collar blazers, open-collar shirts, and pressed slacks. In less formal attire, Dekker sported mock turtlenecks, bombers, and casual khakis. 

As menswear transitioned to the peacock fashions of the 1970s, so did the Rude Boy. Crooning tunes from his albums Trojan and Rhino, Dekker wore sharp getups like an all-red velvet 1970s leisure suit and a pair of checked slacks paired with a loose V-neck top and a camouflage cap. Through Dekker’s Rude Boy style, he displayed and celebrated his Kingston roots.

Alongside the celebrity of singers like Desmond Dekker, the sartorial influence of Rude Boys became an international phenomenon after mass Jamaican immigration to Great Britain in the 1960s and 1970s. Rude Boy style caught on with young British men and converged with local fashion cultures. 

Today, Rude Boy fashion has garnered worldwide acceptance, frequently appearing on runways and in editorials. In light of its current cosmopolitan status, it’s important to remember those young men in Kingston. Rude Boys demonstrated that clothing can subvert stereotypes and amplify one’s voice when ignored or silenced. Who knew a trilby and a pair of brogues could be so radical?

For more on how the Rude Boy influences modern fashion, check out the book Return of the Rude Boy, by Dean Chalkley and Harris Elliott, or read “Saga Bwoys and Rude Boys: Migration, Grooming, and Dandyism,” by Michael McMillan. To learn more about the history of Black dandyism, read Slaves to Fashion: Black Dandyism and the Styling of Black Diasporic Identityby Monica Miller.

About Sierra Holt

Sierra is a New York-based writer and producer originally from Southeastern Ohio. She is in her second year in the Biography & Memoir program at CUNY’s Graduate Center. Sierra creates content focused on fashion, Appalachia, and women’s history.  Her current work includes producing the podcast Ink Slingers, collecting oral histories, and writing biographies.