Amy Sherald’s Portraits Have Injected the Genre with New Life, But They Also Flatten Blackness

In Amy Sherald’s unique visual language, muted yet commanding Black subjects are set against bold color fields. These eye-catching portraits reward longer looking. Her subjects, donning carefully selected garments, face audiences directly with quiet dignity, their skin painted in shades of gray. Sherald’s elegant compositions celebrate various American visual traditions, from fashion spreads and clothing advertisements to historical painting from John Singer Sargent’s intimate society portraits and Grant Wood’s distinctly American regionalism to Kehinde Wiley’s contemporary reframing of historical portraiture, though hers are refracted through a lens that subtly questions these traditions even as it engages them.

Bringing together some 40 portraits across nearly two decades of her career, Sherald’s current survey at Whitney Museum in New York (through August 10) invites us to see how the artist, who rose to international acclaim after painting Michelle Obama in 2018, has reimagined portraiture while posing deeper questions about identity and American mythology. These tensions—between beauty and complexity—remind us that reimagining national identity requires not just new images, but new ways of seeing.

Visitors will likely recognize Michelle LaVaughn Robinson Obama (2018), the 6-foot-tall painting in which the former First Lady appears monumental yet approachable in her geometric patterned dress against a soft blue backdrop. While the Michelle Smith–designed dress has been compared to Piet Mondrian’s spare, primary-color compositions, Sherald has said that in the bold, patchwork-like geometry she sees echoes of the visual language of the Gee’s Bend quilters, the cohort of Black women from rural Alabama whose work merges abstraction, utility, and ancestral memory. This overlooked reference subtly re-centers Black vernacular creativity as a foundational influence, challenging dominant narratives in fashion and design while anchoring the painting within a deeper, more nuanced cultural zeitgeist. The painting’s loan from the National Portrait Gallery in Washington, D.C., speaks to its significance, while its placement—on its own wall facing a bench for contemplation—in Sherald’s retrospective reinforces how it simultaneously builds on the artist’s earlier work and points toward to her more recent direction.

The exhibition, which debuted at the San Francisco Museum of Modern Art last November, is organized chronologically and includes early works like Hangman (2007) and Well Prepared and Maladjusted (2008), which illustrate Sherald’s style as she was developing it. In these formative pieces, we see the artist experimenting with her now signature technique of grayscaling skin tones, though with more tentative color relationships and less refined compositional strategies. The latter work, for example, highlights her emerging interest in how clothing communicates identity. The female subject, wearing a pink gingham shirt, her hair styled in a neat updo, stands against a muddy blue background overlaid in parts with a spongey pink cheetah print that forecasts the more assertive color juxtapositions of Sherald’s later works. In They Call Me Redbone, but I’d Rather Be Strawberry Shortcake (2009), the artist’s visual approach has fully formed. Here, Sherald’s take on clothing, color, and posture as they relate to identity lies front and center in this portrait of a woman in a yellow dress, her hands in her pockets and her head tilted inquisitively. The title, like many Sherald chooses, adds complexity to the calm visual presentation. Strawberry Shortcake asserts her chosen name, amplified by a strawberry pattern on the bodice of her dress and the nearly solid strawberry pink background. She dares you to call her Redbone. 

The portraitist’s more recent large-scale paintings, on the other hand, demonstrate how her take on size and composition have evolved. In A Midsummer Afternoon Dream (2020), a woman in a blue dress stands beside a white bicycle, gently occupying the space in front of a bright green lawn with a white picket fence; the scene deliberately recalls, and then revises, mid-century American domestic ideals. At 8.8 by 8.4 feet, the work translates portraiture into its own environment entirely, immersing the viewer in Sherald’s vision of Black leisure and belonging in spaces historically coded as white.

That depiction of a mid-century Americana that now includes Black people is further evident in a work from a year later, As American as apple pie (2021). In this double portrait, a couple stand in front of a yellow house and vintage car, the woman wearing a pink skirt and matching “Barbie” T-shirt, and the man in sand-colored chinos, a white T-shirt, and a vibrant denim jacket. Sherald’s growing interest in subverting American iconography not only questions the historical exclusion of Black Americans but also aims to normalize Black presence within the visual canon through a restrained aesthetic. Even the title’s reference to that classic dessert amplifies the narrative, inserting Black subjects into the visual language of American identity.

A God Blessed Land (Empire of Dirt), from 2022, similarly expands this purview, showing a Black man on a green John Deere tractor against a clear sky. The painting reconfigures American farming imagery, placing Black presence in the mythic landscape of American agriculture, a realm from which Black Americans have been systematically pushed out. That he stands atop this piece of machinery, as if further proof of his victory over the land, adds to this narrative of reclamation against a history of enslavement and forced manual labor. The subject’s confident pose and direct gaze make viewers reconsider who belongs in this quintessentially American scene.

Smaller works, like 2020’s A bucket full of treasures (Papa gave me sunshine to put in my pockets…), show a more intimate side of Sherald’s practice. The portrait depicts a young man in a white shirt embroidered with a yellow sun and red lobster; the pale-yellow background hinting at innocence and affection. The title suggests personal memory and family connection, themes that run throughout the exhibition but feel especially moving in the artist’s depictions of children and young adults, like in Innocent You, Innocent Me (2016) of a teen boy holding an ice cream cone and wearing a camo Marvel T-shirt.

It’s worth noting that the exhibition title, “American Sublime,” intentionally places Sherald’s work both within and against art historical tradition. Sherald offers a different vision of sublimity from the overwhelming natural phenomena that inspire awe or terror that we are used to. Rather than vast landscapes or dramatic scenes, her sublime comes through in the daily experiences of ordinary people, their gazes steady and self-assured—set against backgrounds so uniform they risk quieting the very individuality her portraits aim to elevate. This points to a significant reimagining of a concept that, in Western art history, has rarely centered the Black experience.

While Sherald’s painting skill and compositional strength are evident, her aesthetic choices also raise important questions. Her signature rendering of Black skin in gray tones, meant to transcend racial categorization, creates a beautiful but potentially problematic distance. In removing the specificity of skin tone, Sherald risks aestheticizing Blackness in ways that might accidentally sanitize the lived realities of racial experience. The cool, composed manner of her subjects, while dignified, sometimes feels detached in ways that might unintentionally reinforce rather than challenge the flattening of Black identity.

To this end, although Sherald’s use of American visual motifs questions dominant narratives of national identity, her consistently calm, controlled visual interpretation sometimes works against the complex, varied nature of the Black American experience. Though visually striking, the artist’s stately style at times contradicts what her work otherwise suggests: that Blackness and Black people aren’t monolithic. The similar emotional tone across her portraits—consistent across age, gender, or setting—offers stunning coherence but occasionally limits her subjects’ expressive range. That said, these tensions don’t diminish Sherald’s contribution; overall, they reflect the built-in challenges of making work that functions as celebration, critique, and revision of American visual culture all at once. In Sherald’s hands, the American sublime is not found in the vastness of nature or the spectacle of power, but a space where individual humanity becomes transcendent.