The Miraculous Masculinity of Gladys Bentley

Gladys Bentley: blues singer, tuxedo wearer and lady lover. In the words of Saidiya Hartman in her book Wayward Lives, Beautiful Experiments, “Bentley was abundant flesh, art in motion.”1 In the words of Bentley herself, from 1952 when she had left the stage and all that came with it, “a big, successful star – and sad, lonely person.”2 There are many ways to read Bentley’s life, but the lens through which I view it is, of course, clothing. In this post, I am going to assess why the clothes worn by Bentley didn’t just have such an impact when they were first worn and paraded around the streets of New York City, but why they have continually influenced queer culture and fashion. 

Gladys Bentley was born in 1907 and lived until 1960. She ran away from her home in Philadelphia at 16, fleeing to a new life in New York City. When she reached New York, she quickly auditioned with a Broadway agent, and recorded eight record sides before ever having been on stage – but the stage was where Bentley’s career took off. She got her first job as a pianist at a club after the male pianist there had suddenly left. She 

finally convinced [the club owner]. My hands fairly flew over the keys. When I had finished my first number, the burst of applause was terrific. One of the white customers walked over, handed me a five dollar bill and said: 

“Please play something else. We don’t care what it is. Just play. You’re terrific.”3

Her salary quickly went up and up, and her name – as well as her sometimes-stage name, Barbara “Bobbie” Minton – rose to fame. She became ingrained within New York City’s nightlife and one of Harlem’s queer celebrities. She was well-known as a “bulldagger.” She had female lovers, left right and center. She was married in a civil union to another woman, speculated to have been a white woman. She crossed boundary lines of race, class, sexuality and gender. 

Fig. 1: Gladys Bentley, c. 1940. Silver and photographic gelatin on photographic paper. Smithsonian National Museum of African American History and Culture.

So far in this article, I have referred to Bentley with she/her pronouns, because this is what was done while Bentley lived (at least, in the media) and in most retrospectives about Bentley’s life. At points, I may continue to do so; Bentley’s existence was a fluid one in many regards. However, other writers have chosen to use “he” to refer to Bentley, at least while he was at the height of his career. This is not to deny his lesbianism, but to acknowledge his specific masculinity. Hartman, who I quoted early on in this article, writes about Bentley as a storyteller would, as if he were depicted in a film.4 

This can be compared to Alfred Duckett’s 1957 article ‘The Third Sex,’ about the “fascinating and unbelievable” phenomenon of lesbianism. In it, he writes that “In her private life, she readily admits, Miss Bentley was a “man” and the husband to a number of women, both coloured and white.”5 If Bentley was indeed living as a man privately, then this is another argument for using “he/him.” However, In Bentley’s autobiographical article ‘I Am A Woman Again’ (which I’ll return to later), we read that “Like a great number of lost souls, I inhabited that half-shadow no-man’s land which exists between the boundaries of the two sexes.”6 This, in my eyes, seems an indication that they/them pronouns might be appropriate to use. 

Because I do not have one solid answer, throughout the rest of this article I will fluctuate between “she” and “they”, or just using “Bentley” wherever possible. I do not want to deny the possibility that Bentley may have identified as a man, or – had the term been available – as non-binary, but I want to understand their masculinity as part of a lesbian history, and as part of lesbian fashion. They were consistently referred to as a “bulldagger” or “bulldike”, and their place within lesbian history has already been firmly established. Bentley, and the clothes that they wore, are part of lesbian fashion history, but they are also part of so much more. Bentley was primarily a musician, but it is their clothing that has preserved their image for a century. 

Fig. 2: Gladys Bentley, c. 1925-1939. JD Doyle Photographs, JD Doyle Archives.

The above photograph is of Bentley wearing one of their typical outfits – a tuxedo, complete with top hat and cane – at some point during the peak of their career. Bentley described their dress at this period when they wrote ‘I Am Woman Again’: “From Harlem I went to Park Avenue. There I appeared in tailor-made clothes, top hat and tails, with a cane to match each costume, stiff-bosomed shirt, wing collar tie and matching shoes. I had two black outfits, one maroon and a tan, grey and white.”7 Although the tuxedo in the above photograph seems white, this may be due to the photograph itself being in black and white – it’s very possible that it pictures the “tan, grey and white” outfit that Bentley describes.

The outfit is flawless, from the fit to the sheen on the fabric to the gloved hands, one on a cane, the other in a pocket. Not just anyone could wear it. The fact that Bentley was so different was their strength – at least for a time. They were seen as a masculine woman, a male impersonator, and an unabashed lesbian. They couldn’t be avoided, in their glossy, expensive costumes and equally fantastic street clothes. They were Black and fat and so talented, so captivating, that they left their audiences begging for more. In the words of Regina V. Jones in her article ‘How Does A Bulldagger Get Out of the Footnote? Or Gladys Bentley’s Blues’: “She physically occupied a privileged space exuding a confident, Black lesbian masculine sexuality.”8

Bentley knew that it was difference, as well as talent, that cemented their audiences, knew that although “I had violated the accepted code of morals that our world observes […] the world has tramped to the doors of the places where I have performed.”9 Their clothing, combined with their talent, was Bentley’s unique selling point. However, Bentley existed past the walls of the club; they walked the streets of Harlem in men’s clothing, with pretty women on their arms; they visited the opera with their “wife”, while “wearing a full dress suit.”10 They inspired young lesbians, other gender non-conforming women and modernist female husbands. They could do all this, at least for a time, because their fame made them near-untouchable. 

It didn’t last. Bentley became too well-known, the United States too scared of Black and queer deviance. In 1940, Bentley was no longer allowed to wear trousers for her act at a bar she frequently performed in, Joaquin El Rancho. It was, as described by Regina Jones, a “perceived fashion transgression.”11 The fashion of Gladys Bentley was what signposted her for deviance – for homosexuality – more than any of her private actions, or even suggestive lyrics. Her proud, loud relationships with women were picked up on, and as the US edged towards McCarthyism and the mid-century, The U.S. House Committee on Un-American Activities investigated Bentley. Her difference was becoming not so desirable as it had once been.12 

Fig. 3: Photograph of Gladys Bentley, c. 1927-1945. Silver and photographic gelatin on photographic paper, owned by Laura Cathrell. Smithsonian National Museum of African American History and Culture.

There was a limit to how much masculinity Bentley could possess within one lifetime. When it was hers it was hers alone, but at other points it was up for grabs. Sometimes, she had to shape her masculinity and her identity with pieces and remnants of past or future lives. A publicity photograph, above, shows her with lipstick and shaped eyebrows, which made her image less troublesome to the gender expectations of the world. Earlier in her career, before her fame transformed her tuxedos into armour, she wore skirts for her acts. She describes how “I wore immaculate white full dress shirts with stiff collars, small bow ties and skirts, oxfords, short Eton jackets and hair cut straight back.”13 

This was perhaps the look that sat the most comfortably  within a long lineage of butch/stud/bulldagger/invert dressing, where a skirt is what makes a blazer and bowtie allowable; Radclyffe Hall, author of lesbian novel The Well of Loneliness wore a similar configuration of garments throughout her life, while butches in the 1950s would often wear tailored skirts with man-tailored shirts as a masculine-yet-safe daytime ensemble.14 Bentley’s tuxedos were so unusual that they were, for a time, allowable. She was a spectacle. The “mannish street garb”, as pictured below, never held the same appeal. Bentley the celebrity did not exist without trousers, top hat and cane.

Fig. 4: Bentley in “mannish street garb” with long-time friend Willie Bryant. c. 1925. In Gladys Bentley, ‘I Am Woman Again,’ Ebony Magazine, Aug. 1952. JD Doyle Archives, via

The big mystery of Bentley’s life story is how she ended her career married to a man, wearing women’s clothing and declaring in the 1952 edition of Ebony magazine that “I Am A Woman Again.” At least, without social context this appears to be a mystery. When you know that Bentley had been finding it increasingly more difficult to work in the way she once had, due to censorship and growing concern about the morality of her lifestyle, it makes sense as the only option to preserve her career. I do not believe for a second that Bentley became “Woman Again” because she wanted to, but rather because she had to. 

In the 50s, for the Ebony feature, Bentley is pictured in long dresses, with shoulder-length curled hair adorned with flowers and a full face of make-up. In many images, she is surrounded by men, which serves to make the distinction between masculine attire and the clothes on her body even starker. In her own account, she describes how a doctor had prescribed her with female hormones, which would “affect me greatly.”15 Her difference, her love of women, her fashion – these all had to go. They had to be eradicated. 

In Saidiya Hartman’s Wayward Lives, she considers Bentley as having “nothing feminine about him; it was more than glamour drag, more than a woman outfitted as a man, as several of his wives, both white and coloured, could attest.”16 If Bentley was not in drag when they performed, nor when they traversed New York throughout the 20s, 30s and 40s, they were in drag when they appeared in the pages of Ebony, ready to convince a world that was against them that they were something acceptable, harmless, and cured. Gladys Bentley’s clothing shaped her image throughout her life, but an image is a fragile thing. It can be changed at the literal drop of a hat. If becoming a woman – and the association here is a heterosexual woman – was the way to survive, then that’s what Bentley did. But “becoming” only reaffirms what Bentley knew throughout her life: that “becoming” can be undone, and the way that we are known is fluid. 

What remains is Bentley’s influence. In Wayward Lives, Hartman also writes about Mabel Hampton, a dancer during the Harlem Renaissance and one of the co-founders of the Lesbian Herstory Archives: “Mabel learned a lot from [Bentley] about claiming a space in a world that granted you none.”17 Bentley represented the power of the presence of a Black bulldagger. Bentley represented a link in a chain of drag kings and male impersonation. Bentley represented how our clothing can shape our place in the world and that, though sometimes we dress to quieten ourselves, the times that we were loud live on. 

Thank you for reading this post on Dressing Dykes! If you enjoyed, feel free to follow me on Instagram or Twitter or support me on Patreon.


1: Saidiya Hartman, Wayward Lives, Beautiful Experiments (London: Serpent’s Tail, [2019] 2021), 197.

2: Gladys Bentley, ‘I Am A Woman Again,’ Ebony Magazine, Aug. 1952, JD Doyle Archives, via 93-94.

3: Bentley, ‘I Am A Woman Again,’ 94.

4: Hartman, Wayward Lives, Beautiful Experiments, 194.

5: Alfred Duckett, ‘The Third Sex,’ The Chicago Defender (National Edition), 2nd March 1957. ProQuest Historical Newspapers: Chicago Defender, 7.

6: Bentley, ‘I Am A Woman Again,’ 93.

7: Bentley, ‘I Am A Woman Again,’ 94.

8: Regina V. Jones, ‘How Does A Bulldagger Get Out of the Footnotes? Or Gladys Bentley’s Blues,’ Awakening 1.31 (2012), 4.

9: Bentley, ‘I Am A Woman Again,’ 93.

10: Duckett, ‘The Third Sex,’ 7.

11: Jones,  ‘How Does A Bulldagger Get Out of the Footnotes?’ 9.

12: Steven J. Niven, ‘Blues Singer Gladys Bentley Broke Ground With Marriage to a Woman in 1931,’ The Root, 11th Feb. 2015.

13: Bentley, ‘I Am A Woman Again,’ 94.

14: Alix Genter, ‘Appearances Can Be Deceiving: Butch-Femme Fashion and Queer Legibility in New York City, 1945-1969,’ Feminist Studies 42.3 (2016): 609.

15: Bentley, ‘I Am A Woman Again’ [no page number].

16: Hartman, Wayward Lives, Beautiful Experiments, 199.

17: Hartman, Wayward Lives, Beautiful Experiments, 337.

4 thoughts on “The Miraculous Masculinity of Gladys Bentley

  1. Thank-you, Eleanor for your piece on Gladys. One note, the photo of Bentley and Willie Bryant is probably closer to c. 1935. The posters advertise Bryant’s band, which he formed in 1934 and the Ubangi Revue at the Apollo. The Ubangi Club was open from 1934-37. It was common for clubs to send their revue’s to theatres like the Apollo, Lafayette and Lincoln in Harlem so the locals could enjoy the great talents, playing shows before they would perform at clubs, a practice known as doubling. Langston Hughes writes about Bentley too.


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