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In 2017, Sherald was invited to create the official portrait of First Lady Michelle Obama. Although this was her first commission, she approached it as she had all her previous portraits: she focused on the essence of her subject. As Sherald has stated, “I wanted to produce something that . . . alluded to the nuances of who [Obama] really is versus who she has to be.” When choosing Obama’s clothing for the portrait, a dress by Milly designer Michelle Smith, Sherald was drawn to its contemporary quality and geometric print, which reminded her of patterns used by the Gee’s Bend quilters in Alabama. She then photographed Obama in natural light, capturing her in an open and unguarded pose.
The painting breaks significantly with the conventions of state portraiture, presenting Obama as gracious and comfortable, but also inward-looking and self-contained. The latter is an especially notable achievement, given that Obama’s movements, statements, and appearance were and still are subject to endless public scrutiny. In Sherald’s painting, Obama is both a Black woman from the South Side of Chicago and the ultimate African American first: a Black First Lady who is the descendant of enslaved Africans. As a result, while no less poised or formal, Sherald’s powerful portrait has more in common with her paintings of everyday Black people than with the depictions of any of the first ladies who preceded or followed Obama.