While Smith had worked with Obama on several occasions prior to the portrait, the designer was still pleasantly surprised when stylist Meredith Koop approached her to create a custom dress based on a piece from Milly’s spring 2017 collection. Often, several designers are commissioned to create pieces for occasions like this, but only one gets selected, which is why Smith prepared for a different dress to be picked, especially given the printed design. “When they told me the dress that they were interested in from my runway show, I was surprised because it was so kind of fashion-forward and revealing,” says Smith, referring to the often-conservative, solid-colored ensembles that get picked for National Gallery’s portraits.