The Secret Meaning Behind Michelle Obama’s Milly Dress in Her Official Portrait


A REAL FRAME JOB: Milly founder Michelle Smith was first tipped that Michelle Obama would be wearing one of her dresses for an official portrait six months ago. Obama’s stylist Meredith Koop had put the word out but the designer had no idea Monday would be the official unveiling of artists Amy Sherald’s painting at the National Portrait Gallery.

Smith said via Monday e-mail, “I just arrived in Paris for work, so I found out with everyone else. I was in a shop buying jeans when my PR called. I started flipping out at the cash wrap.”

She said she was so honored to “be a small part of American history and most importantly, the Obama legacy. The Obamas will be remembered for breaking down barriers within race, gender and sexual orientation. They will be remembered for their humanity and kindness.”

Smith, whose art collection includes work from John Baldessari, Natasha Law, Margeaux Walter and Tony Scherman, has collaborated with artist and filmmaker Laurie Simmons (better known as Lena Dunham’s mother), and graffiti artists Michael De Feo and Peter Miser for different projects. She was also high on the former First Couple’s choices of artists — Sherald and Kehinde Wiley. “Each has a very distinctive, personal style and signature to their work. Their art speaks to everyone about the African-American experience. Their art and style is so very much of our generation. I wonder what people will think 300 years from now, gazing at these paintings in awe. The works are waaaay more conceptual and forward-thinking than presidential portraits of the past,” she said.

The Milly founder said she has met Michelle Obama on several occasions. “Most notably, I was invited to the Obamas’ final party in the White House, which took place last January. It was the best night of my life. No phones were allowed inside, so everyone let loose, was in the moment, and had a wonderful time. No one wanted to leave. I think Andy [Oshrin, her husband and business partner] and I staggered out around 4 a.m.”

As for how it is having Michelle Obama wear one of her designs for the Sherald painting, Smith said, “This ranks top, top, top without a doubt. Forever. But I’m going to keep on working. I love to create clothes that make women feel confident, empowered and beautiful.”

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