The Columbus Museum of Art hosted an exhibition of his work in 2007 and describes his paintings as "heroic portraits which address the image and status of young African-American men in contemporary culture.

[13] Wiley has said that his family survived on welfare checks and the limited income earned by his mother's "thrift store"—which consisted of a patch of sidewalk outside their home.

[13] Kehinde Wiley is an American portrait painter who paints monumental works of art that captivate audiences with bold colors and strong views on racial power.

[18] When later commenting on his fascination with the mugshot and its influence in his art, Wiley noted that when he found it on the street, it altered his view of what portraiture could be and solidified his feelings about the portrayal of black men in the world.

[18] Wiley's Rumors of War is a bronze sculpture that commemorates African American youth lost to the social and political battles being waged throughout the nation.

These have included Brazil, Nigeria, India, and China because Wiley states that he understands all of these as "points of anxiety and curiosity and production" to the world.

[22] While other presidential portraits show their subjects in a more realistic representation with an office in order to communicate their authority,[22] Wiley depicted Obama seated casually on an antique chair, seemingly floating among foliage.

[26] Wiley also mentioned in the unveiling of Obama's portrait that he went to museums in Los Angeles and noticed that there weren't many artworks that display African Americans; he wanted to change that.

Rumors of War was unveiled in Times Square before being moved to the Virginia Museum of Fine Arts, a mile away from the J. E. B. Stuart statue which inspired it and the institute that commissioned it.

[41] He also curated a group show of African arts featuring Nigerian artist Oluwole Omofemi at the Jeffrey Deitch Gallery in Los Angeles.

Rendering his figures in a realistic mode—while making references to specific Old Master paintings—Wiley creates a fusion of period styles and influences, ranging from French Rococo, Islamic architecture, and West African textile design, to urban hip hop and the "Sea Foam Green" of a Martha Stewart Interiors color swatch.

Wiley depicts his slightly larger than life-size figures in a heroic manner, giving them poses that connote power and spiritual awakening.

Wiley "investigates the perception of blackness and creates a contemporary hybrid Olympus in which tradition is invested with a new street credibility".

Although seemingly naturalistic, both Wiley's and David's portraits feature rider's who are disproportionate to their steed, because "men look a lot smaller on real horses."

Dressed in street clothes, his models were asked to assume poses from the paintings of Renaissance masters, such as Titian and Giovanni Battista Tiepolo.

Wiley depicted the rapper Ice T as Napoleon and Grandmaster Flash and the Furious Five as a Dutch Civic guard company from the 17th century.

[38] A second painting entitled Judith Beheading Holofernes[55] also features a modern-day black woman as Judith and a white woman as Holofernes, challenging the viewer's expectations of this familiar motif, inviting political readings, and "bending a violent image from art history—which is rife with them [...]—to the needs of a country that is reexamining the violent underpinnings of even its most benign-seeming traditions.

"[56] Art critic Walter Robinson remarks that this reimagining of the Judith/Holofernes story "suggests, with a jovial brutality, that Judith would prefer to be done with white standards of beauty.

This is an intentional choice by Wiley to reflect on the lack of female figures in art history in portraits due to societal norms.

The patterns of lace and flowers are often associated with femininity and by submerging his male figures in these ornate backgrounds, Wiley acknowledges the beauty and youth of his subjects.

In the recreation of these 18th century portraits, modern black men that he meets on the streets are taking the place of the original subjects, they are assuming their position or power.

[58] The original portraits that Wiley recreates would have hung in lavish homes of the wealthy amongst other extremely detailed ornaments to further enhance the wealth of the homeowners.

[58] By replicating these patterns and motifs from opulent decor and other elements of interior design and encapsulating his figures within them, Wiley is recreating a similar sense of wealth with his portraits.

[citation needed] Two of Wiley's paintings were featured on the top of 500 New York City taxi cabs in early 2011 as a collaboration with the Art Production Fund.

[64] Kehinde Wiley: A New Republic, was a retrospective at the Virginia Museum of Fine Arts (Richmond, VA), in the summer of 2016 (June 11 – September 5).

Awuah-Darko claimed that he was first "inappropriately groped" shortly after meeting Wiley, and then was subject to a "much more severe and violent" assault later that day.

Lawyers for Wiley sent Awuah-Darko a cease and desist letter demanding the removal of his "categorically false and defamatory" Instagram posts.

[65][66] Following Awuah-Darko's posts, three more individuals accused Wiley of sexual violence: activist Derrick Ingram, artist Nathaniel Lloyd Richards, and photographer Terrell Armistead.

[71] In response, Wiley said that the allegations were "completely false" and a "social media-driven fabrication" that distracted from his traveling exhibition "An Archaeology of Silence".

[69][72] The National Coalition Against Censorship called the allegations against Wiley "serious and concerning" but criticized the museums' decision, arguing for placing problematic artists in context rather than canceling them.