Una, Lady Troubridge by Romaine Brooks; oil on canvas, 1924. Collection of the Smithsonian American Art Museum.
Boy am I excited to see this painting in person! It’s going to be installed in a section of Youth and Beauty: Art of the American Twenties that collectively fits the theme of “Close-Ups: Scrutiny, Perfection and the Twenties Portrait.”
I forget how I first stumbled across the work of female artist Romaine Brooks. According to art historian Frances K. Pohl, who writes about Brooks in , “The painter Romaine Brooks (1874-1970) …devoted her career to the depiction of the lives and looks of those engaged in same-sex relationships. An American born in Rome into an extremely wealthy family, Brooks inherited the family fortune in 1902, and subsequently moved to Paris… (and) in 1915 became part of a community of women devoted to the production of art.” (p.332) Romaine Brooks painted a self-portrait  (now in the Smithsonian American Art Museum, Washington, DC) wearing attire similar to that worn by Lady Troubridge- white shirt, dark jacket; essentially, menswear.
When I first saw these images I thought of Marlene Dietrich- the famous image of her wearing a tuxedo and a top-hat - which, whenever I first saw it, did not register to me as “cross-dressing”. I thought of it as confident and attractive (perhaps because menswear has been a staple of American women’s clothing for decades now). But at the time, Marlene Dietrich, Romaine Brooks, and Una, Lady Troubridge, would have been seen as cross-dressing “others”. This was apparently a way to signify one’s sexuality or play with gender orientation in the 1920s.
According to the Smithsonian American Art Museum’s website description  of Una, Lady Troubridge, Brooks “intended the portrait to be a caricature of her friend as a headstrong, demanding woman, and noted in a letter that this was “a sign of the age which may amuse future feminists.”” Indeed!
-- Alicia Garr