In his work, Wiley references Western European portraiture in what he calls “urban-meets-classical” style. By presenting his contemporary subjects in these formats, Wiley purposefully departs from a style of portraiture that was historically reserved for elites. He juxtaposes modern urban culture with art-historical convention to make a provocative statement about the hierarchical nature of Western society. In Wiley’s words,
Kehinde Wiley (born February 28, 1977) is a New York City-based portrait painter who is known for his highly naturalistic paintings of African-Americans. The Columbus Museum of Art, which hosted an exhibition of his work in 2007, describes his work as follows: "Wiley has gained recent acclaim for his heroic portraits which address the image and status of young African-American men in contemporary culture."In October 2017 it was announced that Wiley had been commissioned to produce a portrait of former U.S. president Barack Obama for the Smithsonian National Portrait Gallery. This painting was unveiled on February 12, 2018. He and Amy Sherald, whose portrait of former First Lady Michelle Obama was simultaneously unveiled, are the first black artists to paint official portraits of the president or First Lady for the National Portrait Gallery. Wiley has received criticism in association with commissioning him for the Obama presidential portrait, as he has produced two painting variations of Judith Beheading Holofernes where Wiley depicts African-American women holding the severed heads of white women, which Wiley says is a "play on the 'kill whitey' thing".
“The phrase ‘an economy of grace’ speaks directly to the ways in which we manufacture and value grace and honor, the people that we choose to bestow that honor upon, and the ways in which grace is at once an ideal that we strive for and something that is considered to be an natural human right. I am painting women in order to come to terms with the depictions of gender within the context of art history. One has to broaden the conversation… This series of works attempts to reconcile the presence of black female stereotypes that surrounds their presence and/or absence in art history, and the notions of beauty, spectacle, and the ‘grand’ in painting.”