Discovering My Femininity in Menswear


My mother wanted a ballerina, but I’ve always been more of a cowboy. Mayfair Academy of Fine Arts has been serving Chicago’s predominantly black South Side since 1957. Lured into classes by tap dance, I was entrapped into years of ballet sans tap. Tears always accompanied those Saturday morning classes of taunts by cliques of pre-pubescent prima donnas. I sought refuge in my room, skinny legs wrapped protectively in durable jeans, hidden from the jeers of my peers.

I always equate dresses with two things: unsolicited commentary on my size and impracticality. I was a cowboi, not the woman forced to sit side-saddle–restricted to following or falling; never fighting or leading the cavalry. Dresses signified damsels in dis-dress (see what I did there?).

Even when women characters were badass, a frequent mark of their capture was being forced into a dress. Think Selena (Naomie Harris) in the zombie-apocalypse thriller 28 Days Later; upon her capture by the all-male military faction desperate for female companionship rape. Selena spent the majority of the film as a leather trench coat wearing, machete wielding badass. Once captured, the militia’s first action is to force Selena and her teenaged charge into dresses. Dresses were for tripping up women characters for the quintessential fall. They were tools of inequality leaving women easily accessible.


Dresses did not make me feel feminine; they made me feel vulnerable. I realize that vulnerability is a key element to the social construct of the feminine; and make no mistake, my critique of dresses is purely about their function for the socially-constructed feminine perpetuated in media and culture. Of course I find them aesthetically pleasing–I just don’t enjoy how I feel wearing them.

“My mom was adamant that we couldn’t wear pants to church. I wore dresses and skirts for a very long time. I took one for the team when I wore a dress for my sister’s wedding. That was the very last time about 11 years ago.”–Anna DeShawn, Founder/CEO of E3 Radio

anna deshawn

The first steel horse that I owned was a bicycle that epitomized the feminine: banana-seat; sunshine yellow paint; tassels; and a mesh basket. It did not match the stallion nor Harley Davidson of my imaginary as I pedaled twice as hard to keep up with the boys on the block. I yearned for the rugged rubber of their BMX tires. More importantly, I began to realize that their masculinity (nascent as it was) afforded them a freedom of adventure and beingness of which I was excluded. My mother wouldn’t allow me a dirt bike, and the 1980s did not produce a female version splattered in pastel pinks and yellows with a slanted frame bar. My only recourse was to ditch the basket, rip off the tassels, and switch out the tires. Before gender neutral bikes, there was my transgender one.

I take issue with gender binaries–that there is either masculine or feminine. The very notion of how the words function is problematic and was evident the first time I wore a bowtie. It did not imbue me with masculinity. I did not become butch, stud, or any other masculine-male identity. It did, however, provide a buffer for me to experience some of the liberties attributed to the masculine. My mannerisms and behaviors were no longer regulated by my style of dress.

dappervista pic

Regardless of how I was perceived–femme-bodied, masculine of center/androgynous–the shift was in how I felt. I felt free to be me–at times feminine, masculine, androgynous or combinations of them such that classifying bowties, neckties, suits and wingtips as menswear becomes extremely oppressive. The clothing allows me to embrace myself fully. As one who felt dresses to be too difficult a performance, it was masculine attire that provided the outlet for my range of gender identity, particularly for my repressed feminine energy.

I try not to worry about labels too much, but the one most commonly used when describing me has always been a “tomboy.” As I’ve grown into adulthood and the LGBT community, I am also associated with words like androgynous or AG (a description commonly used in NYC).” –Danielle Cooper, Founder & Editor in Chief of

From Sojourner Truth’s assertions in “Ain’t I A Woman?” to the misogynistic insults hurled at Serena Williams’ body, women of color have continuously been excluded from the social constructions of “womanhood.” Masculine of center, queer women of color are even more affected by these definitions and their associated violations. To be a queer woman of color in “menswear”’ is an act of resistance on multiple levels. It is the embodiment of intersectionality. It asserts womanhood on its own terms while embracing historically problematic associations. It’s the equivalent of eating a fried chicken and watermelon dinner in public (because fried chicken and watermelon are delicious) and daring anyone to attribute the meal to its racial stereotypes. Menswear-inspired clothing intervenes into traditional constructions of womanhood.

“I am obsessed with menswear. I always have been. When I was younger, I was all about sweatpants and oversized clothing because of basketball and ’90s trends. As I’ve matured, so has my style. I’ve fallen in love with suiting and tailoring over the years and continue to mix my love for suits and streetwear in a fun way that represents me.” –Danielle Cooper

shes a gent

I sometimes wonder what life would be like without such strict gender categories. My love affair with “menswear” is a direct result of fleeing the limitations of women’s wear and its signification of inequality.

As an adult, I asked my mother why she tortured me with ballet. She replied, “To get rid of that country gait of a walk you have.”

“Did it work?” I asked.


Always a cowboi.

M. Shelly Conner is a Chicago-based writer, humorist, and scholar. Her writing has appeared in The Feminist Wire, xoJane, Black Girl Dangerous, Skin to Skin Magazine, and The Frisky. She is currently exploring publishing options for her debut novel “everyman “(forthcoming excerpt in Obsidian Journal). She is Executive Director of Quare Square Collective, Inc. – a 501(c)(3) nonprofit for queer artists of color. Follow her blog about travel, culture and food through a queer womanist of color lens at

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