Every three years, the Smithsonian’s National Portrait Gallery hosts the Outwin Boochever Portrait Competition, considered one of the most prestigious of its kind in the United States.
Named after longtime docent Virginia Outwin Boochever, whose endowment funds the event, the competition reviews thousands of entries from both emerging and established artists, with finalists across multiple disciplines ultimately presenting a celebration of modern American portraiture—not to mention a visual representation of this country today.
This is the competition that helped launch the career of then-Baltimore-based painter Amy Sherald, who won first place in 2016. She would go on to create the official portrait of former First Lady Michelle Obama—now on view in her American Sublime exhibition at the Baltimore Museum of Art through April 5, which was originally slated to be held at this very location.
Now, Baltimore is once again making its mark on the Outwin. Out of this year’s 34 finalists, three local artists are represented in the competition’s culminating exhibition, The Outwin 2025: American Portraiture Today, now on view through August 30 in Washington, D.C., plus one area teen has taken home a youth prize.
Learn a bit more about their talents, below, then hop on a quick train to the nation’s capital to experience their pieces for yourself.
J.M. Giordano
Local photojournalist J.M. Giordano was selected as an Outwin finalist for his 2023 portrait titled “Yvonne Freeman on Her Ancestral Ground.” Captured through a fading window frame, this powerful photograph was shot on assignment for Baltimore magazine, accompanying a story on the historic African-American “Hill” community on Maryland’s Eastern Shore.
A former City Paper staffer, Giordano’s work—which ranges from city streetscapes and slice-of-life snapshots to documentary-style civic reporting—has been featured in the likes of NPR, The Guardian, The Washington Post, and Rolling Stone. He has also published multiple books, such as We Used to Live At Night and Trumpland. His latest exhibition, The Secret City: New Works in Color Film, is currently on display at The Peale.
LaToya Hobbs
Born and raised in Little Rock, Arkansas, Hobbs is an artist and Maryland Institute College of Art (MICA) educator who has been building her name on both the local and national arts scenes. Winner of the 2020 Janet and Walter Sondheim Artscape Prize, her work has been exhibited from City Hall is held in the private collections of the Baltimore Museum of Art.
She’s known for her large-scale paintings and prints of Black women, incorporating woodcut, collage, and rich patterns that make her subjects come to life on the canvas. Hobbs sees portraiture as a powerful tool of representation. Her Outwin selection is the sepia-hued “Erin and Anyah with Hydrangeas,” capturing the potent abundance of youth like a summer evening.
Katie O’Keefe
Not your standard portrait, “Entwined Repose” is a three-dimensional self-depiction of the artist herself in search of comfort. In shades of red and pink, the MICA fiber-arts graduate and Baker Artist Portfolios semifinalist tosses and turns in an internal struggle with the notion of rest in the face of a chronic Lyme disease diagnosis.
Created with both machine and hand embroidery on fabric in 2022, this “mending” also serves as a metaphor, with O’Keefe seeing her art as a form of healing. A New York native, her contemporary work has been exhibited at a variety of local spaces like School 33, Gallery CA, and the Baltimore Jewelry Center.
Matilda Myers
In addition to the main event, the top prize of the Outwin Teen Portrait Competition, for teen artists in the 13 to 15 age group, was awarded to “Tilly” Myers—a junior at George Washington Carver Center for Arts and Technology, who happens to be the daughter of Baltimore contributing photographer Christopher Myers.
In her photograph, “Rest”—on view in a video presentation on the NPG’s second floor—a ballerina stretches in the shadows beside a pickaxe, juxtaposing the masculine and feminine, as well as shadows and light. “Tilly brings a great narrative to all her photographic work, especially her portraits,” said Carver instructor Sherry Insley, in a statement.
