Reimagining Classical Art: A Deep Dive Into Kehinde Wiley's Groundbreaking Style

A black woman in a navy blue ball gown sits on a golden brown chaise lounge with turquoise blue cushions. She makes eye contact with the viewer against a vibrant green foliage background adorned with blue flowers.Image © Kehinde Wiley Studio / Juliette Recamier © Kehinde Wiley 2012
Leah Mentzis

Leah Mentzis, Partnerships Manager[email protected]

Interested in buying or selling
an artwork?

Browse artworks

MyPortfolio

With his vision, technique and subversive approach, Kehinde Wiley breathes new life into classical art to show us how history reflects on the contemporary era. Wiley's distinctive style combines art historical references, cultural representation, and meticulous technique to create intimate portraits of individuals that simultaneously speak volumes about the racial politics of history, culture and society. By examining his groundbreaking style, it is possible to unearth the influences, themes, and symbolism that define Wiley’s artistic identity. As a maker of paintings that expand and advance traditional portraiture, he stands as a modern master who will undoubtedly influence the course of art for years to come.

A young tattooed man stands staring at the viewer with his hands on his hips. His shirt is off, and his head is tilted at an angle.Image © Kehinde Wiley Studio / From The Coronation Of The Virgin © Kehinde Wiley 2005

Undoubtedly, Kehinde Wiley is a visionary force. Having achieved widespread popularity and recognition in his relatively early career, his artistic project is concerned with redefining the relationship between classical art and the present day. With his remarkable reinterpretation of classical art, Wiley has captured the attention of art enthusiasts, collectors, and scholars alike.

Understanding Wiley means exploring the rich tapestry of influences, themes, and symbolism that define his artistic identity. As an artist, his evolution has produced a unique approach to figurative painting that fuses masterful craftsmanship with a deep exploration of Black identity and representation. His majestic portraits—at once vulnerable, majestic and subversive—provoke viewers to question the status quo of cultural norms and hierarchies, a feat that has transformed him into a powerful figure in contemporary art.

Through the lens of Wiley's captivating artworks, audiences can navigate the intersections of art history, culture, representation and artistic innovation. By critically analysing his art, we uncover the subtle nuances and intricate layers of meaning that lie beneath the surface, fostering a greater appreciation for the technical prowess and political consciousness embedded within his artistic vision.

The Journey and Influences Behind Kehinde Wiley’s Artwork

Kehinde Wiley’s journey from South Central Los Angeles to a presidential painter is a remarkable story of talent, determination, and inimitable artistry. Wiley displayed a passion for art from an early age, with his mother enrolling him in art classes at the age of 11. He went on to study at the San Francisco Art Institute and later earned his MFA from Yale University. It was at Yale that he became a comfortable and expressive portrait artist, selling his work to friends and peers to fund his way through his studies.

Wiley's artistry draws inspiration from a wide array of sources, blending elements of art history, street culture, and contemporary fashion. The electric appeal of his work is grounded in a bold exploration of power, identity, and representation. By reimagining historical works and placing Black individuals in postures and surroundings traditionally reserved for white authority figures, Wiley challenges traditional narratives and confronts societal constructs. His meticulously rendered backgrounds and postures serve as a defiant visual commentary on the historical exclusion of Black subjects from art historical narratives.

Two black men in jeans and vibrant oriental patterned zip-up jackets. One man poses with his hand near his crotch while the other raises his hand in a performance stance. The second man gestures with one hand and points to his palm with the other, facing the viewer. The scene is set outdoors with a golden sky, a pink path, and lush green bushes.Image © Kehinde Wiley Studio / The Tribute Money © Kehinde Wiley 2011

Wiley's style is characterised by an elegant realism, using attention to detail, vibrant colours, and intricate patterns to capture the individuality of his sitters. With his larger-than-life ornate portraits, his work exudes a grandeur and majesty that forms a direct dialogue with classical portraits of the past. Through his art, Wiley seeks to disrupt conventional notions of power and beauty, elevating the visibility of Black individuals both in the art world and physical gallery spaces.

The visionary essence of Wiley’s work is evident through his numerous accolades, including being the first Black artist to paint an official U.S. presidential portrait for the National Portrait Gallery. His work has been exhibited in prestigious institutions such as the Musée de l'Orangerie in Paris, the National Gallery in London and Brooklyn Museum in New York.

In Wiley, we encounter an artist whose unwavering dedication to reinterpreting classical art and amplifying marginalised voices has redefined contemporary art. His unique artistic approach continues to inspire and challenge audiences, reminding us of the transformative power of art in shaping our perception of culture, history, and society at large.

Two tall black women in white ball gowns, crossing over their shoulders, stand side by side. One woman extends her dress outward while both link arms and make eye contact with the viewer. They are positioned against a black background with ornate pink, yellow, and green floral foliage.Image © Kehinde Wiley Studio / The Two Sisters © Kehinde Wiley 2012

An Archaeology of Silence: Wiley's Exhibition at De Young Museum

Currently at the De Young Museum in San Francisco, An Archaeology of Silence has proven one of Wiley’s most impactful exhibitions. This captivating showcase gets to the heart of Wiley’s artistic philosophy and the profound themes of representation and race politics that permeate his work. At the same time, the impressive range of mediums and techniques employed by Wiley is in full view.

Large equestrian statue and large-scale portrait from Kehinde Wiley exhibition: An Archaeology of Silence at the De Young in San Francisco.Image © Stephen Friedman Gallery / Picture from Kehinde Wiley: An Archaeology of Silence exhibition at the De Young Museum, San Francisco © Kehinde Wiley 2023

Previously exhibited at the 59th International Art Exhibition La Biennale di Venezia, Kehinde Wiley: An Archaeology of Silence the series expands on his 2008 series DOWN. This was initially inspired by Holbein’s famous work, The Dead Christ in the Tomb, as well as broader classical references to depictions of fallen warriors and still angelic figures. While disrupting the narrative of classical art, the series also injected with a harrowing message about the violence, pain and injustice inflicted on Black communities through history and the individual loss that goes with it.

In, An Archaeology of Silence, Wiley continues to engage with the histories of colonialism and racialised hierarchies in America and beyond, this time using the visual vocabulary of the fallen hero. Specifically, the series mediates the killings of young Black men all around the world. Exhibited in the wake of the murder of George Floyd and continuing instances of police brutality, Archaeology of Silence takes on a sense of pain and urgency, connecting historical racialised injustice with a grim ongoing reality. As Wiley explains, “That is the archaeology I am unearthing: The spectre of police violence and state control over the bodies of young Black and Brown people all over the world.’’

The exhibition at De Young Museum unveils a rich tapestry of Wiley's portraits, inviting viewers into a world where historical narratives intersect with contemporary realities. Unlike Wiley’s other series, his subjects are posed in positions of vulnerability—but they retain the essence of majesty that runs through the artist's portraiture. Adorned with what Wiley terms ”21st-century markers’’ such as branded clothing and personal jewellery, the portraits tell individual stories that not only function as eulogies but also defiant proclamations of endurance. Situated as the subjects of Western ecclesiastical and classical works, each sitter transcends the corporeal and assumes the visual language of martyrdom and sainthood.

Depicting Power, Creating Representation: Wiley's Artistic Journey

Kehinde Wiley's artistic journey is defined by his unwavering commitment to depicting power and creating representation for those who have been historically marginalised. Through his art, Wiley takes issue with societal norms and challenges the lack of diversity within the traditional canon of portraiture.

Central to Wiley's approach is street casting, which he uses as a form of political and social commentary, inviting viewers to critically examine the dynamics of power and how cultural representation shapes our perceptions. His portraits, characterised by their exquisite attention to detail and vibrant colours, serve as a visual critique of established hierarchies, challenging Westernised and colonial notions of beauty and worth.

Wiley's impact extends far beyond the realm of art. His commitment to social change has inspired countless artists, scholars, and activists to explore the transformative potential of art. His work has become a touchstone for those who seek to challenge inequities, spark dialogue, and forge new paths within the art world and society at large.

A triptych-style artwork, designed to resemble a stained glass altarpiece, portrays a black man standing on a raised platform in the middle panel. The platform is embellished with a gold plaque. The man is casually dressed, wearing denim jeans, a denim vest, and a blue long-sleeve striped shirt underneath. The background behind him is navy blue, with a golden circle positioned behind his head. The artwork is adorned with intricate red and green borders.Image © Kehinde Wiley Studio / Saint Adelaide © 2014

Light and Darkness in Wiley’s Work: Illuminating America's History of Racism

In Wiley's art, the radiant light of Renaissance masterpieces intertwines with the weight of America's dark history of systemic racism. Wiley’s careful use of light and colour serves as a powerful tool to explore and reflect upon the complex intersections of race, history, and beauty.

Echoing Renaissance styles and the luminous works of artists like Titian and Caravaggio, Wiley infuses his portraits with a captivating play of light. This technique not only enhances the visual impact of his paintings but also carries symbolic significance. For Wiley, luminosity serves as a metaphorical illumination, shedding light on the often overlooked contributions and experiences of Black individuals.

In Wiley’s work, the very act of playing with light is politically weighted. While the mastery of light and shadow by Renaissance painters is often lauded by art historians, this was adapted almost exclusively for white subjects. It was during his time at the San Francisco Art Institute that he realised he would need to evolve these classical techniques to depict Black skin tones accurately.

As he explains: “There’s a tradition of learning how to create shadows and light and moulding the body into something that’s beautiful that I learned through painting whiteness. You fast forward to the present day when I’m working globally and exploring the far ends of Senegalese deep, deep, deep Black skin tones… it becomes this interesting play on light and colour that has very little to do with the classical Western notions of playing with light.’’

In the portrait, a black man exudes confidence as he gazes directly at the viewer. He is stylishly attired in white trousers, a white shirt, and a white fur jacket. One hand rests on his hip, revealing a visible flip phone attached to it. Around his neck, he wears a chain, and he holds another chain between two fingers, allowing it to dangle gracefully.Image © Kehinde Wiley Studio / Madonna Of The Rosary © Kehinde Wiley 2005

Resplendent with vivid hues and richly textured backgrounds, Wiley’s portraits become a stage for narratives that challenge historical traditions. By depicting people of colour in the grandeur of traditional European portraiture, Wiley reclaims and recontextualises art history, inviting viewers to question the ways in which race and identity have been depicted and constructed throughout the centuries.

Wiley's exploration of light in his art serves as a beacon, illuminating the profound connections between the art of the past and the challenges of the present. By harnessing the transformative power of light, he highlights the resilience, strength, and beauty of those who have historically been marginalised, offering a counterpoint to the shadows cast by America's dark legacy of racism.

In the center of the portrait, a young black man captures attention with his street-style ensemble. He wears a white t-shirt beneath a blue basketball sports jersey, and a blue paisley bandana adorns his head. His gaze locks onto the viewer as he assumes a prayer pose, with his hands clasped in front of him. Against a vibrant red backdrop, adorned with yellow flowers, the young man stands out. The artwork is further enhanced by intricate and ornate vibrant green elements. The portrait is elegantly framed in gold.Image © Kehinde Wiley Studio / Saint Francis of Assisi © Kehinde Wiley 2005

Exploring Kehinde Wiley's Artistic Style

With his ultra-detailed portraits, at first glance you might be forgiven for mistaking Kehinde Wiley for a photographer. In truth, his style of painting is as distinctive as it is captivating. Through a careful combination of elements, he creates a visual language that is uniquely his own and contributes to an unmistakable painterly presence.

A defining aspect of Wiley's style is his sharp attention to detail. His portraits are meticulously rendered, showcasing precision and technical skill that sets him apart as a virtuoso painter. Every brushstroke and intricately depicted pattern adds depth and richness to his compositions.

Wiley's bold approach to colour is another hallmark of his style. Vibrant and saturated hues leap off of Wiley’s canvases, infusing his portraits with energy and vitality. This deliberate choice of colour amplifies the presence of his subjects, imbuing them with a sense of power and commanding attention.

In terms of techniques and processes, Wiley employs traditional oil painting techniques, such as glazing and layering, to achieve a luminous and realistic quality in his work. Through this classical technique, he is also able to draw a direct line between his own work and art historical tradition in order to question the lack of Black portraiture in the European canon.

Wiley’s process also borrows some techniques from classical painters like Michelangelo, who were known for using artists' assistants in their work. Following suit, Wiley employs up to ten artist assistants for his large-scale works. However, Wiley’s sourcing of his models outrightly breaks with art historical tradition. Taking to the streets to cast his sitters, Wiley’s process rests on the depiction of ordinary individuals who are willing to take part in his project.

Resemblance to the grandeur and regal portraiture of the Old Masters is integral to Wiley’s work—but his reinterpretation of classical art with contemporary subjects distinguishes him as a pioneer in his own right. His fusion of historical references with the aesthetics of modern Black culture creates a unique visual dialogue that pushes artistic boundaries.

With its meticulous detail, vibrant colours, and fusion of techniques, Wiley’s style is an extraordinary blend of past and present. Through his engagement and expansion of tradition, Wiley has pioneered the art of portraiture, weaving together diverse influences to create a visual language that resonates with contemporary audiences.

In a circular vignette-style portrait, a tall and slender black man is depicted wearing traditional lavender Muslim clothing. He stands confidently with one foot extended outward, and his hand rests gracefully on his hip, while his other arm bends across his chest. The portrait is set outdoors, underneath a green tree adorned with yellow flowers, although the tree itself is intentionally cropped out of the composition.Image © Kehind Wiley Studio / Portrait of Denola Grey © Kehinde Wiley 2023

Beyond Kehinde Wiley: Other Artists Reimagining Classical Art

Wiley's groundbreaking approach to reimagining classical art speaks to a movement that extends beyond his own remarkable body of work. Numerous contemporary artists are engaging in similar endeavours, reshaping artistic conventions and challenging traditional narratives.

One artist working in a similar vein is Mickalene Thomas. Like Wiley, Thomas reinterprets classical portraiture but with a focus on female subjects, exploring notions of beauty, race, and gender. Her mixed-media works incorporate bold patterns, collage elements, and rhinestones, creating visually striking compositions that challenge established norms.

Another artist reimagining the canon of art and portraiture is Jordan Casteel. Casteel's large-scale, intimate portraits capture her interest in the relationship of her sitters—usually Black men and women—to their everyday surroundings. Much like Wiley’s, Casteel’s sitters exude a sense of dignity and presence, but with a sharp focus on contemporary day-to-day life. Through her distinct use of colour and composition, Casteel invites audiences into the personal realms of those she captures, simultaneously depicting the minutiae and fullness of their lives.

The overarching significance of artists like Wiley, Thomas and Casteel lies in a shared ability to disrupt historical narratives and make their mark on modern ones, amplifying voices that have been excluded from dominant dialogues. By reimagining classical art, these artists challenge the canon and expand our understanding of representation. Their work sparks conversation on themes of identity, power, and cultural heritage, fostering a more varied and stimulating art landscape.

The Enduring Legacy of Kehinde Wiley's Art

Kehinde Wiley's art speaks to the power of representation and what it tells us about power. His groundbreaking style and reinterpretation of classical art have left a poignant mark on the global stage of contemporary art, captivating audiences and challenging traditional narratives.

Wiley's portraits turn subjects into agents; he invites them to take centre stage in their own representation. At once, Wiley’s sitters assume and subvert the grandeur of art history. His use of vibrant colours, meticulous attention to detail, and fusion of techniques create a visual language that not only bears the defiance of his artistry but also proves his status as master of the portrait.

The enduring legacy of Wiley's art lies in its ability to inspire, provoke, and push the boundaries of what is possible within the realm of contemporary art and cultural representation. From his presidential portrait to sitters from the streets of Harlem, it is clear that Wiley has redefined representation.