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Why Do People Think Men Who Wear Women's Clothing Are Gay?

When Young Thug debuted the cover for JEFFERY, he raised interesting questions about why, exactly, we conflate men who wear women's clothing with homosexuality.

The cover for Young Thug's latest mixtape, 'JEFFERY'

Last month, when the rapper Young Thug released his latest mixtape, JEFFERY, it wasn't his singsong "post-verbal" hooks that got all the attention, nor its celebrity-studded track list, in which each song is named after his idols. Instead, it was the ruffled, periwinkle Alessandro Trincone gown and cocktail parasol hat he modeled for the cover that went viral.

It wasn't the first time Thug donned women's clothing for catwalk-inspired style. Since his rise to popularity, he has made flirting with gender fluidity and androgyny central to his image, going so far as to say he believes "there's no such thing as gender" in a recent Calvin Klein ad spot.


Fans and critics responded with starkly contrasting opinions. To some, Thug's gender-bending style was groundbreaking, especially in an industry defined by hyper-masculinity. To others, he was appropriating queer culture. (The latter is not an unfounded accusation, given some of the rapper's lyrics.) But the knee-jerk reaction of some social-media users was to question the rapper's sexuality, which raises a larger—and more interesting—question: Why do so many people label a man wearing women's clothing "gay" in the first place?

To be sure, Thug is far from the first male musician to wear a dress—the legacy of cross-dressing rock stars stretches back decades, from David Bowie to Prince. He isn't even the first rapper to play with gender expectations in his style. But examining the reaction to Thug's apparel choices underscores a specific fact: that a man who transgresses the arbitrary rules of what "masculine clothing" can be still spurs controversy in 2016. This stems from the fact that gendered clothing relies on the rigid constructs of masculinity and femininity. A man veering too far in the wrong direction on this binary is pejoratively deemed "gay," for example, not conforming to the relatively strict visual codes associated with "real men," a conclusion that seems to spring from the same fallacy that says gay men exhibit feminine characteristics, and that any man demonstrating effeminate qualities must be gay.


If the whole scenario sounds childish, that's probably because it's rooted, at least partially, in the recent origin of markedly distinct clothing for boys and girls.

Clothing historian Jo Paoletti, a professor of American studies at the University of Maryland, has spent nearly four decades researching gender difference in fashion. In 2012, she published a history of children's clothing, Pink and Blue: Telling the Boys from the Girls in America, which chronicles the decline of gender-neutral apparel for babies and toddlers and the rise of highly gender-specific clothes in the mid 80s, explaining how consumerism helped drive the rapid move toward gendering clothing for young children.

In seeing the social-media response to Thug's apparel, she questions whether there's a childhood connection there.

"I wonder how much of that is us going back to how we were at four or five years old," Paoletti told VICE, explaining how toddlers acquire enough cultural capital to know whether they're something called a boy or a girl.

Children from the age of two to around six rely on cultural cues; they don't yet understand biological sex, Paoletti explained. "At that age, what makes a little boy a little boy is what he's wearing, what his hair looks like, what he plays with," she said. "And if he has long hair, wears something different or plays with something a girl would play with, that makes him a girl in their minds."


"We've got a whole generation of people—anyone born after 1985—who, from their earliest years, were surrounded by these very binary representations of gender," she added, more or less describing the vast majority of Thug's millennial audience.

Looking at how those listeners responded to the "JEFFERY" cover art makes clear a longstanding double standard: that women can openly wear men's clothes, as long as they don't go too far, but a man wearing a dress remains a social taboo. In fact, in female fashion, "tomboy" looks are more than acceptable—they're downright stylish. A number of brands, like WILDFANG, capitalize on the connotation.

That's not to say women who wear "masculine" apparel are completely within the bounds of social norms, but they're generally more accepted than a man who may wear "feminine" looks. Vera Wylde, the cross-dressing persona of a straight man in Vermont, believes the contradiction is rooted in sexism—toward women.

As a drag performer and vlogger, Wylde—who uses feminine pronouns when in character—often fields assertions that she must be gay. "People question my sexuality all the time," Wylde told VICE. "The popular belief is that men who dress as women, particularly if they perform for the public in drag, are attracted to men.

"I think this comes from the still deeply set belief that men are somehow superior to women," added Wylde. "If a woman wants to look more like a man, that might be odd, but it's almost aspirational. A man wishing to appear and behave more like a woman is seen as a downgrade, as the man choosing to be less than he is."


Some may think this issue is insignificant, but these power dynamics don't seem trivial when examined among children.

"This is why a girl dressing up as a pirate or a cowboy is just adorable, and a little boy wanting to dress up as a princess is shocking, scary, and grounds for beating the little kid — which happens," said Paoletti. "Maybe if people stop thinking the way they're thinking there will be fewer two-year-old boys who get beat up—by their parents, in many cases."

Indeed, in an interview with Billboard published online last week, Thug spoke to the ways in which his own parents could react to style that misaligned with gender: "When I was 12, my feet were so small I wore my sisters' glitter shoes. My dad would whoop me: 'You're not going to school now, you'll embarrass us!' But I never gave a f— what people think."

As society increasingly wrestles with the tangible influence gender and sexual binaries have in our lives, it's a good bet that musicians will continue to see how challenging these constructs prompts heated discussion. And whether you consider it expedient art or internet trolling, this won't be the last time we see a dude wearing a dress set on riling the masses.

As questions continue to swirl about whether Thug's fashion choices signify progress or exploitation or something else entirely, the incident makes one thing clear: "We are totally confused and misinformed," says Paoletti, "and we're still acting like a bunch of four-year-olds."

Follow Jon Shadel on Twitter.