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Penned By: The Dapper Boi
In honor of Black History Month, we want to highlight queer black icon and pioneer of gender-nonconforming fashion Gladys Bentley. Bentley, who went by the stage name Bobbie Minton, was a Harlem Renaissance blues singer who pushed the envelope of gender, sexuality, class, and race—both personally and professionally. She was one of the most well-known and financially successful black women in the United States during the 1920s and 30s.
Bentley was born in 1907, the eldest of four children. From an early age, she reported wearing her younger brother’s suits to school, a behavior her parents tried (and failed) to “correct.” Eventually, she ran away from home at the age of sixteen to make as a talented pianist and blues singer in New York City.
Early on, Bentley would often incorporate overtly sexual song content, stage moves, and attire into her act, a thrilling and scandalous contribution at the time. As a result, she did not have the same name recognition as some of her Harlem Renaissance peers. The risqué nature of her performances kept her out of mainstream venues, newspapers, and even history books. In recent years, however, she’s finally received some long overdue recognition as the unapologetic queer black icon she really was—someone ahead of her time who pushed boundaries.
Within the underground speakeasy scene, Bentley was known for her signature look: a black-and-white tuxedo complete with top hat and tails. She was revolutionary in her masculinity. Unlike traditional male impersonators or drag kings of the time, Bentley did not try to “pass” as a man. Instead, she exuded a “black female masculinity” that blurred the line between masculine and feminine, between black and white.
At the height of her fame and success, Bentley owned a Park Avenue apartment equipped with domestic workers and other luxuries. This was quite an accomplishment for a black female artist in the 30s, especially one who was openly gay. But after the repeal of Prohibition, which led to closure of many speakeasies she would perform at, her popularity waned.
Eventually she moved to southern California and lived a relatively quiet life until the 1940s. She saw success again during World War II, a time when gay bars began popping up around the West Coast. Unfortunately, Bentley died suddenly and tragically after contracting pneumonia in 1960 at the age of 52.
As an LGBTQ+ owned business that specializes in gender-neutral and size-inclusive clothing, Bentley’s courageous and uncompromised individuality really resonates with us. Her story serves as an inspiration—a reminder to always keep pushing the boundaries of what’s possible, to change what’s “acceptable,” and to be grateful for how far we’ve come.
During her career, there came a point where Bentley had to carry special permits that allowed her to perform in men’s clothing. One can only speculate what she would think about the gender-neutral revolution taking place in today’s fashion. We’d like to think she’d be proud. We know we are.