#Outwin2025

Portrait of Michelle Obama

Michelle LaVaughn Robinson Obama

by Amy Sherald
Oil on linen, 2018

Michelle Obama remembers growing up on the South Side of Chicago and thinking, “being smart is cooler than anything in the world.” After earning degrees from Princeton University and Harvard Law School, she joined Sidley Austin LLP, where she met Barack Obama in 1989. Guided by the desire to improve her community, she left the firm in the mid-1990s to begin a career in public service. She directed community and external affairs for the University of Chicago Medical Center prior to moving to Washington in 2009.

During her husband’s two presidential campaigns, Mrs. Obama delivered poignant speeches that centered on her family’s commitment to serving others and highlighted the importance of her role as a parent. As first lady, she focused on women’s rights, LGBTQ rights, children’s health, and military families.

Mrs. Obama selected Amy Sherald, winner of the 2016 Outwin Boochever Portrait Competition, to create her official portrait for the museum. The Baltimore-based artist considers the former first lady to be someone “women can relate to—no matter what shape, size, race, or color…We see our best selves in her.” Here, she portrays Mrs. Obama as both confident and approachable, in a dress by Michelle Smith’s label Milly.

National Portrait Gallery, Smithsonian Institution; Gift of Kate Capshaw and Steven Spielberg; Judith Kern and Kent Whealy; Tommie L. Pegues and Donald A. Capoccia; Clarence, DeLoise, and Brenda Gaines; Jonathan and Nancy Lee Kemper; The Stoneridge Fund of Amy and Marc Meadows; Robert E. Meyerhoff and Rheda Becker; Catherine and Michael Podell; Mark and Cindy Aron; Lyndon J. Barrois and Janine Sherman Barrois; The Honorable John and Louise Bryson; Paul and Rose Carter; Bob and Jane Clark; Lisa R. Davis; Shirley Ross Davis and Family; Alan and Lois Fern; Conrad and Constance Hipkins; Sharon and John Hoffman; Audrey M. Irmas; John Legend and Chrissy Teigen; Eileen Harris Norton; Helen Hilton Raiser; Philip and Elizabeth Ryan; Roselyne Chroman Swig; Josef Vascovitz and Lisa Goodman; Eileen Baird; Dennis and Joyce Black Family Charitable Foundation; Shelley Brazier; Aryn Drake-Lee; Andy and Teri Goodman; Randi Charno Levine and Jeffrey E. Levine; Fred M. Levin and Nancy Livingston, The Shenson Foundation; Monique Meloche Gallery, Chicago; Arthur Lewis and Hau Nguyen; Sara and John Schram; Alyssa Taubman and Robert Rothman © National Portrait Gallery