Florence ("Flossie") Pierce was the daughter of a lighthouse keeper who lived on an island off the coast of Maine, where artist George Bellows spent several summers. In this portrait of her, Bellows experiments with bold color arranged in large blocks. At the same time, he suggests a complex psychological presence conveyed by the brightly lit gaze of his subject.

Bellows was associated with the Ashcan School, a group of painters in New York City who celebrated everyday subject matter in paintings of the urban scene. His energetic style and broad brushwork won immediate praise and recognition, and at the age of 27, he was elected as one of the youngest associates in the history of the National Academy of Design. Four years later, in 1913, he became an academician and exhibited in New York's landmark Armory Show (International Exhibition of Modern Art). His exposure there to modern European art is evident in the heightened color, and concern for form and structure, seen in Portrait of Florence Pierce. The dramatic lighting and loose paint handling, especially beautiful in the sitter’s foreshortened arm and hand draped over the chair back, are characteristic of the powerful, realistic portraits that Bellows painted throughout his career.