Miguel Street is a collection of interconnected stories set in a poor, working-class neighborhood in Port of Spain, Trinidad. The stories are told through the eyes of a young narrator who observes the lives of his neighbors, each with their unique personalities and struggles.

The book is structured in a non-chronological way, with each chapter focusing on a particular character, but with characters from previous chapters reappearing as minor characters in subsequent ones. Through these stories, Naipaul paints a vivid picture of the community and its struggles.

The first story, "Bogart," introduces the reader to the character who gives the book its name. Bogart is a charismatic man who has made himself popular by creating a mysterious persona as a tailor who never sews, and an imitation of the American actor Humphrey Bogart. He disappears from time to time, returning with elaborate stories of his adventures, which become more and more like those of an American gangster. However, Bogart's real problem is that he is unable to father a child with his wife in Tunapuna, so he impregnates a girl in Caroni, and is forced to marry her. Although he is arrested for bigamy, he still impresses the men on Miguel Street because he has proven his virility. His need to prove himself as a man among his peers ultimately leads to his downfall.

The second story, "Popo," is about a man who, unlike Bogart, is initially seen as weak and unmanly by the other men on Miguel Street. However, when he deserts his hardworking wife and becomes drunk, angry, and rowdy, he is finally accepted as a man. His reputation dwindles when he brings his wife back and remodels the house to please her, but he once again impresses the community when he is arrested for stealing materials and furniture. Unfortunately, his return from prison sees him turn industrious, which disappoints the men on Miguel Street, who believe that profitable employment should be left to women.

Miguel Street has additional tales of various characters, each of whom faces their individual challenges. The arrangement of the book establishes a thematic connection between the stories, with every chapter building upon the previous ones. For instance, George is an outcast who constantly beats his wife and children, while his son Elias struggles to pass exams but never complains about his job as a cart driver, despite his father's abusive behavior.

The book also features stories about characters who are pretenders, like B. Wordsworth and Big Foot, who both disappear when their cowardice becomes general knowledge. The final sketch in this group is about Morgan, the maker of fireworks and a would-be comedian, who also has to flee from the judgments of the Street.

The last three stories in the book are about characters who keep their places on Miguel Street and become friends of the narrator. Titus Hoyt, Laura, and Eddoes all give appropriate gifts to the narrator at the end of the book. Hoyt is a teacher who moves from one pedagogical project to the next. Laura is a prolific mother who moves cheerfully from pregnancy to pregnancy. The final story in this group is about Eddoes, a determined survivor who finds joy in the discards of others, which he finds at the dump, and eventually in a discarded baby, supposedly his.

The book does not develop chronologically, but it ends with the narrator becoming an adult and leaving Miguel Street to acquire an education. Unlike many of the characters in the book, the narrator has a real opportunity to alter his life, and he does so by leaving the community and pursuing higher education. The book's themes of aspiration, defeat, and adjustment are universal and relatable, making it a timeless work.