Michelle Obama’s Portrait Dress Made History. Here’s How It Came Together

When Michelle Obama’s official portrait, painted by Amy Sherald, was unveiled in 2018 at Smithsonian Museum's National Portrait Gallery, it was praised for its showcase of vibrant colors. In it, the former First Lady is shown sitting against a sky-blue background in a white-and-black maxi dress with pink, red, and chartreuse graphic squares designed by Milly’s then-designer Michelle Smith. Since its unveiling, the dress has become an important chapter in American fashion history. So much so that, in 2021, the museum exhibited the gown alongside the portrait. Now, it is being further immortalized in the new Showtime series The First Lady, starring Viola Davis as Obama. 

Four years later, Smith is still wrapping her head around the historic moment: “To be a small part of the Obama legacy and how they're remembered through that portrait through that visual of the dress, it's an incredible honor,” says the designer, who left Milly in 2019 and is currently designing her own namesake line.

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. 

For instance, Laura Bush opted for a navy gown with a shirt-like neckline and a drop waist. Eleanor Roosevelt and Betty Ford, who are also depicted in Showtime’s new series, donned equally somber outfits: a pale blue suit and a light blue turtleneck dress with draped cape, respectively. 

While different from the looks that came before, Obama’s portrait dress was emblematic of the style that defined her while she occupied the East Wing, which progressed from pencil skirts, cardigans, and pearl necklaces early in her husband’s term to shoulder-baring dresses, metallic gowns, and vibrant pops of color. Even more notably, the former First Lady made it a point to wear as many clothes by up-and-coming American designers, including Prabal Gurung and Thakoon, as well as international designers during her time in the White House, which made a dress from Milly an especially fitting choice.

The look also embodied the optimism that surrounded President Barack Obama’s two terms in office, which saw historic policy changes from the legalization of same-sex marriage to the repealing of “Don’t Ask, Don’t Tell.” Smith says this sentiment was also a defining theme for the collection from which the dress was pulled. “The feeling of it was optimism toward women's rights and toward equality," she says.

After customizing the dress, Smith spent months communicating with Koop, who, according to the designer, would send images of Obama’s fittings with notes of changes and adjustments. The final product was a white halter maxi dress with a flowing skirt that featured blocks of color that Sherald compared to Dutch artist Piet Mondrian’s work. 

“[After completing the dress,] I didn't hear anything for a while,” Smith says. “A few months later, Meredith called me to tell me the news but I was in the middle of preparing for an upcoming fashion week, so I filed it in the back of my mind.” When the portrait was finally unveiled, the designer was in Paris choosing textiles for a new collection. “I was probably the last person on the planet to know when it was announced [because of the time difference],” she says. “I wish I could have been in the United States for that moment, but it was kind of fun just being alone in Paris and having that moment to myself.”

While Smith didn’t get a chance to see the painting at its home at the National Portrait Gallery, she finally had the opportunity to witness her historic mark in American art when the portrait made a pitstop in Brooklyn during the "Obama Portraits Tour" last year. But, as soon as the painting returns home, Smith is hoping to make the trip to Washington, D.C., alongside her two kids.

“[It’s incredible to] realize that one day my kids will take their children to the Smithsonian’s Portrait Gallery, and they'll be able to see the portrait,” she says. “Art lives forever.”