Sherald's creative process began as soon as she learned she'd received the commission, looking up every image of Michelle Obama she could find on the internet. The Obama portrait was a departure for Sherald who had never taken a directed commission before, but in other respects her approach remained the same. She sought to avoid creating a painting that was similar to Obama's "public entity," and instead develop one that was more "private and intimate." Sherald set up photography sessions in D.C. and went through many dresses with Obama's stylist Meredith Koop, with a relatively casual, sleeveless maxi dress from Michelle Smith's Spring 2017 collection for American fashion line Milly as the final selection. For Sherald, the dress connected to the black history of quilting, like those of Gee's Bend. Elements of the portrait have been noted by art critics to have been influenced by Gustav Klimt, in particular the Portrait of Adele Bloch-Bauer I. One commentator noted the similarity to fashion designed by Klimt's muse Emilie Louise Flöge.
