Traditional Notions of Masculinity or Harry’s High Waisted Pants? You Decide


Graphic by Eden Anyabwile

Graphic by Eden Anyabwile

When Harry Styles released his retro-inspired “Watermelon Sugar” video last May— which was cheekily dedicated “to touching” in the opening title— I may have had to go find a cool breeze to stand in afterwards. As I ogled him croon about summer evenings in his crochet crop top and sailor tattoos, I momentarily forgot about unpleasant things like lockdown, isolation or, say, the repressive gender roles codified in our dress code.

Harry consistently challenges gender norms with his attire, and his fans have been here for it. After donning a frilly Gucci dress for the December ’20 cover of Vogue, Harry still shut out the competition for GQ’s Most Stylish Man of the Year. Trevor Noah even gave a nod to the Vogue cover last weekend when he introduced Harry’s Grammy performance with a “He’ll steal your heart and your dress, and he’ll look damn good doing it!”

Indeed, when he stripped off that green faux-fur boa during his performance, my teenage sister started screaming... (okay, so I don’t have a teenage sister).

Intriguingly, Harry’s flamboyant take on fashion has only augmented his status as a sex-symbol, which says as much about his charm as it does the cultural moment. Many believe that fashion both influences and signals societal shifts. If that’s the case, perhaps there’s hope that, finally, a particularly obstinate strain of hyper-masculinity is in retreat.

After watching nonbinary style ricochet off the men’s fashion scene for years, seeing it embraced by the heterosexual mainstream feels significant. The shift is likely due in no small part to Harry’s influence. It seems like every day another male celebrity cops a Styles look— like Justin Bieber trading out his hideous loungewear for a flared swag suit in the music video for “Peaches,” or Cole Sprouse posing in pearls and patent leather pumps. In reality, though, Alessandro Michele’s Gucci revived the glam disco aesthetic— Harry just happened to become their unofficial brand ambassador first.

Since the day his dalliance with the Italian luxury house began, Harry’s bold style has commanded our attention and prompted many, including myself, to re-examine the complex relationship between men’s clothing, sexuality, and masculinity.

The 27-year-old’s style evolution probably began back in 2019 when he stepped onto the Met Gala red carpet sporting a sheer women’s Gucci blouse; his perfect pair of nipples were set off by a single pearl earring. We were all thinking it: was Harry Styles, dreamboat extraordinaire, off the hetero market? Cue millions of Google searches: Is Harry Styles gay?

This reaction is obviously not “woke,” but in our defense, we are trained to infer a man’s sexuality from their ensemble. Many are pushing to shift that cultural norm, however, contending that it prevents men from expressing themselves through clothing, and perpetuates constrictive notions of masculinity.

“We learn our gender as we grow up: from our family, from society, from movies and, of course, from fashion,” says Dr. Alexandra Sherlock, who lectures on fashion as a strategy for social change. “Fashion reinforces these norms, but it can also challenge them.”

Since men are constantly tasked with proving their masculinity, it only stands to reason that this manifests in their style— or lack thereof. Straight-presenting men usually dress in a more subdued fashion than their female counterparts, even if that means they wear the same dismal pants/shirt combinations until they die. With its boxy cuts and lack of variety, male garment design doesn’t lend itself to self-expression: “When we design for women, we acknowledge and consider every part of their bodies,” says design student Adam Kassar. “Somehow, it’s too fanciful to invest that kind of consideration into menswear.”

Harry, on the other hand, has perfected a highly individualistic style, channeling a summer-of-love persona that is Gucci through and through. Heeled boots and voluminous, high-waisted trousers comprise the prototypical Harry Styles uniform, which is often paired with cheerfully colored blouses or scalloped collars that are as comforting as tea with grandma.

 “He has the aura of an English rock-and-roll star—like a young Greek god with the attitude of James Dean and a little bit of Mick Jagger—but no one is sweeter,” Alessandro Michelle gushed to Vogue, subtlety not being among his many talents.

The creative director of Gucci clearly draws inspiration from fantastically dressed rock-icons, and Harry makes it no secret that he does as well: “The people that I looked up to in music—Prince and David Bowie and Elvis and Freddie Mercury and Elton John—they’re such showmen. As a kid it was completely mind-blowing. Now I’ll put on something that feels really flamboyant, and I don’t feel crazy wearing it.”

Flamboyant dressing in straight presenting men is hardly a novel concept—just look at every monarch prior to 1900. In the present day, flamboyance is reflexively associated with femininity, but we forget that many “flamboyant” fashions were considered heteronormative when they were adopted.  

After the introduction of the suit in the 19th century, men’s style bandwidth was drastically curtailed, but there is both historic precedent for men dressing in skirts for practical purposes or resplendent finery as a power move. Fashion lecturer Tove Hermanson points out that ancient men and women wore the same garments. Subtle variations that developed, such as the drape of a woman’s toga, only illustrate that “sex specific clothing is a societal construct that was honed – as gender roles and expectations were—over time.”

Throughout the centuries, gender conventions and apparel have remained in constant conversation with each other. In the 1960’s, as women took on “manly” societal roles like working outside the home and pursuing a career, their changing functions were mirrored in their attire as they began to adopt jeans and pantsuits.

The bold and sexy style of the 60’s and 70’s—think tie-dye, silk shirts, high-waisted flares and jumpsuits—also coincided with the civil rights, gay rights, and women’s liberation movements. There is no doubt that the equality achieved by activists had a generative effect. A certain exuberance and freedom came to life in the music, culture, and fashion of that age— sensual, tight, and expressive clothing were worn by both men and women alike.

With the strange sociopolitical synchronicity between then and now, it’s no wonder Gucci and its initiates are trying to resuscitate that shimmering moment in time. But whatever happened to that moment?

As women continued to put on pants, literally and figuratively, menswear grew baggier and more sedate than ever, as if it were trying to distinguish itself from womenswear. I’m sure a cultural historian could hypothesize as to how or why this occurred, but the shift has been an enduring one. Decades later, it’s considered feminine for a pop star to wear colorful and expressive clothing, and groundbreaking to simply confess, as Harry did, that he finds joy in playing with clothes.

It’s unfortunate that we moved backwards. It’s unfortunate that a young boy should have to measure himself with an invisible masculinity stick every time he gets dressed. I cringe to think of my male peers growing up alongside me in the 2000’s. I’m pretty sure any guy who dared to wear a pink Abercrombie polo had to rehearse “no homo” and “I’m man enough to wear pink” in the mirror before taking a fortifying breath and stepping out the door.

No woman would ever have to do the same—we don’t look at certain colors and worry that they will taint us or rob us of vitality. If you’re a woman, imagine how it feels to slip on a pair or combat boots, or a baggy sweatshirt. If anything, switching up our ensemble with a masculine touch feels empowering and sexy; more like borrowing confidence than losing it. Why don’t men feel the same way? That is a complex question, but it is safe to say that misogyny is a double-edged sword. By objectifying and shaming women, men are deprived of an entire half of the gender spectrum and the natural self-expression found within it.

Iggy Pop is known for saying “I’m not ashamed to dress like a woman because I don’t think it’s shameful to be a woman.” If he really meant it, that would set him apart from most men— even most women. Despite massive strides made by women and LGBTQ people in recent years, femme shaming is deeply entrenched. If that were not the case, men in “feminine” clothing wouldn’t be making headlines in 2021. Nonetheless, identifying hidden outposts of misogyny is certainly a step, or sashay, in the right direction. I’m hopeful we’ve reached critical mass to redefine masculinity on less oppressive terms, and that doing so will demolish unseen barriers for women that persist in the modern day.

There are several methods to fight toxic masculinity, clothing being but one—but there’s no denying its potency. Harry doesn’t speak much about his iconoclastic ensembles, but neither did Bowie. Rather, they let their clothes do the talking. For example, when an interviewer asked Harry if his clothes were his way of clue-dropping hints about his orientation, he demurred, asking simply, “Who cares, does that make sense? It’s just: who cares?

And just like that, he waved away well-established assumptions about dress and sexuality like they were flies around his dinner plate, even whilst continuing to date women and dress like he raided Prince’s closet. He isn’t defensive about being accused of being gay or feminine because he doesn’t see a problem with either of those things. Beyond his clothing and his music, perhaps that is why we are so enamored with Harry. There is a certain weightlessness with which he moves through the world, and his unique brand of confidence is contagious.

I know what you’re thinking, and I’m aware that I’m giving Harry entirely too much credit. Literally all he did is show up and look fabulous, and for some reason he is appointed THE patron saint of non-binary fashion?

It’s true that the shift in men’s fashion is actually the outcome of many influential icons and designers working towards the same vision. It remains to be seen if the look will be a passing trend in fashion, or if non-binary style is the bellwether to a burgeoning social phenomenon akin to the liberation movements of the 60’s and 70’s. In that context, it’s less about Harry as an individual and more about what his broad acceptance says about how far we’ve come. Everyone is gearing up for a second Hot Girl Summer, but maybe we should herald its OG predecessor, the Summer of Love.

Whether the splash Harry has made with his ensembles was intentional or accidental, he demonstrates to the unconvinced that fluidity and individuality are not menacing notions. One only has to watch him perform to be converted— there really is nothing sexier than a person, male or female, who is totally liberated.

So, whether you choose to wear a dress or baggy Carhartts, make like Harry and go do your own damn thing. Why not? Just surrender to the nostalgia, to the melody on the breeze, to the feeling of high-waisted flares caressing your belly button… and imagine a world where you could be exactly who you are without having to be defensive about it. It feels good. It looks good. It tastes like strawberries on a summer evening. You know the rest.