Lena Waithe (Alberto E. Rodriguez)/Getty Images; Gladys Bentley (Wikimedia); Janelle Monáe (Alex Wong/Getty Images)

“Ain’t I a woman?” Black feminist pioneer Sojourner Truth famously asked that question of an all-white audience of abolitionists and suffragettes in 1861, to point out the erasure of black women from the social “protections” of womanhood.

A century and a half later, black women, from Misty Copeland and Serena Williams to first lady Michelle Obama, are still being questioned and criticized for not embodying “traditional” ideals of womanhood. Adding insult to injury, there’s even a segment of black men who consider “the most educated group in the United States” the least desirable.

These opinions—or “preferences,” as misogynoirists often call them—originate in racist beliefs that black women are outside the classical concept of womanhood. This “othering” relies on stereotypes of black women as “angry,” “unwomanly” or “manly” when compared with women of other races. Yet those of us who represent the lifestyle known as “dapper” simultaneously embrace and challenge those stereotypes.

From 1920s-era performer Gladys Bentley to 2017 Emmy Award-winning writer Lena Waithe, black women donning menswear have continually asserted themselves in the intersecting conversations of gender identity, fashion and race. We boldly respond to Truth’s query with a resounding, “Yes, I am.”

These conversations inevitably revolve around being “masculine of center” (MoC), an umbrella term that encompasses all the nuanced characteristics outside of “traditional” femininity—from the tomboy to the butch/stud. “Dapper,” when applied to any and all gender identities, denotes a style of dress noted as much for its precision in execution as its play in pairing. For people of the African Diaspora, it intersects with a cultural history of dandyism best described by Ekow Eshun, curator of the photography exhibit “Made You Look: Dandyism and Black Masculinity.” He describes it as “radical personal politics, a willed flamboyance that flies in the face of conventional constructions of the black masculine.”

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As a dapper queer woman, I’m the beneficiary of evolving social constructs of gender that have far-reaching roots. For instance, to simply say that Harlem Renaissance blues singer Gladys Bentley was a “drag king” is to rely on the limits of language and time. Bentley, an open lesbian, dressed in menswear and sang blues songs about female lovers. In the 1920s, she was described as “performing maleness,” yet Bentley enjoyed same-sex relationships and wore suits and ties offstage, as well. And though gender theorist Judith Butler argues that we’re always performing gender in various ways—including what we wear—perhaps it’s fairer to say Bentley was not performing but, rather, presenting herself as a dapper black woman singing songs of her lesbian experience in an unevolved era.

The misconception that some women dress in suits and ties to either be or imitate men ironically imitates social systems that center men in all things. Speaking for myself, I enjoy the look and feel of how my particular womanhood expresses itself through this style of dress. It isn’t manhood or maleness, but masculinity—a trait most associated with men but not exclusive to them—that I present as a dapper woman. But my affinity for oxfords and bowties have absolutely nothing to do with men.

As Janelle Monáe clapped back at a Twitter user who complained about being “tired of those dumbass suits” she favors: “Sit down. I’m not for male consumption.”

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Janelle Monáe (Bryan Bedder/Getty Images)

Menswear and menswear-inspired clothing embrace masculinity, but not necessarily as a rejection of the feminine. Monáe epitomizes style as statement; using her wardrobe of suits, bowties and monochromatic colors to honor both her and her parents’ uniformed pasts as domestic workers. Similarly, every Eldredge knot I tie and wingtip I slip into honors and frees a little tomboy in late-’70s, early-’80s Chicago, forced into stiff lace-ruffled dresses with matching socks and hand-me-down rabbit fur coats.

As it turns out, I wasn’t the only budding dapper queer suffocating through girlhood on Chicago’s predominantly black South Side. Recent Emmy winner Lena Waithe’s historymaking episode “Thanksgiving” on Netflix’s Master of None serves as an accurate and humorous primer on black queer girlhood. In fact, I watched it with my mother and aunt this Thanksgiving, along with the pilot episode of my own comedy web series, Quare Life (Open TV, beta, 2018).

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Together, these two episodes feature characters rarely represented in a setting often misrepresented: masculine-of-center black women on Chicago’s South Side. If Judith Butler is correct in positing that gender is made up of actions we’ve been socialized to do, maybe coming of age during the rise of hip-hop—which spawned as many unisex fashion trends as misogynist rhymes—influenced Waithe, me and countless girls like us to evolve from baggy sweats and bandannas to tuxedos and bow ties.

Maybe, like Monáe, we dress this way as a statement; paying homage to generations of black girls viewed as masculine by default. But more likely, part of #BlackGirlMagic is to slay in whatever we wear, demanding that onlookers and critics recognize who we are, even when it defies convention. Maybe that’s why, when referencing her Emmy-night tuxedo, Lena Waithe said, “I felt like the queen of the night in that thing.”


M Shelly Conner is a Chicago-based writer, humorist and scholar. She is executive director of Quare Square Collective Inc., a 501(c)(3) nonprofit for queer artists of color. Shelly is also creator of the new comedy web series Quare Life (currently in production with OpenTV). Follow her writings about travel, culture and food through a queer-womanist-of-color lens at DapperVista.com.