The style of Winesburg, Ohio has often been placed at various points in the spectrum between the naturalism of Anderson’s literary predecessor, William Dean Howells (who died almost one year after the publication of the book), contemporaries Theodore Dreiser and Sinclair Lewis, and the Modernist writers of the Lost Generation. In what has been dubbed a "New Realism", Winesburg, Ohio surpasses the notion of the novel as an "objective report" by making use of "lyrical, nostalgic, evocative," even sentimental effects of nineteenth-century novels in its depictions of what lies beneath the psychological surface of a midwestern town. In the book, Anderson reoriented the facts typical of realist novels by incorporating his characters' inner beliefs about themselves as part of "reality".
The symbolism in Winesburg, Ohio plays a large role in allowing for this reorientation. Beginning with the idea of characters as grotesques whose "...grotesqueness is not merely a shield of deformity; it is also a remnant of misshapen feelings, what Dr. Reefy in the sketch 'Paper Pills' calls 'the sweetness of the twisted apples'". The irony of the sweet, but twisted (meaning, in the sentimental Victorian tradition, internally inferior), apples is that they are compared to Dr. Reefy's own knuckles that make a habit of stuffing crumpled notes bearing his thoughts unread into his pockets (itself a symbol of the "ineffectuality of human thought"). Wing Biddlebaum, the subject of the story "Hands", likewise was "...forever striving to conceal [his hands] in his pockets or behind his back". For Wing, his hands were "...the very index of his humanity", with the potential to symbolize a continuum going from a general fear of sexuality to sublimated homosexuality. Wing Biddlebaum and Dr. Reefy are just two examples of how throughout Winesburg, Ohio, Anderson builds myriad themes by adding symbolic significance to gestures, weather conditions and time of day, and events, among other features of the stories.
Another major characteristic of Winesburg, Ohio that separates its style from Anderson's contemporaries, as well as his previous novels, is the minimal role of plot. According to critic David Stouk's article "Anderson's Expressionist Art", "As an expressionist drama, there is little development of a story line in the Winesburg tales in term of cause and effect." Indeed, it is this de-emphasis of traditional story elements in lieu of experimentation with language that provides both a link and a rift between Winesburg, Ohio and the novels of the following decades; whereas the simple, stripped-down vernacular that Gertrude Stein found so appealing in Anderson's writing of the time became an exemplar of quintessential American style most famously associated with Ernest Hemingway, the expressionistic portrayal of emotional states in Winesburg, Ohio was later, by some critics, considered "undisciplined" and "vague".