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Harry Styles can get away with wearing a skirt. But can I? | Men’s fashion

I love clothes, including those defined as feminine. I rarely wear such things outside, because who’s got the guts? This could be the time. Gendered fashion is, reportedly, dead. After wearing lounge pants for two years, men want to liberate their legs. To test the cultural temperature, I’ve borrowed a long black skirt from my friend Rowena, and am wearing it around south London, to see if anyone cares. They do. Men in skirts may be having a moment, but my experience is excruciating. Passersby stare at me with narrowed eyes, like I’m a piece of long division.

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It looks so easy on magazine covers. Harry Styles, Pete Davidson and NBA star Russell Westbrook have burned the menswear rulebook, while celebrities such as Kid Cuddy, Lewis Hamilton and Oscar Isaac are also feted as straight male skirt kings. Thom Browne, Raf Simons, Yohji Yamamoto and Comme des Garçons all pushed the look in recent collections. But catwalks and red carpets are one thing, Peckham Rye in a slitted maxi is quite another. I may as well be wearing a colander for a crown.

The skirt itself is great. Free, airy and elegant. “Is it a man’s skirt?” asks a woman sitting outside a shop. “Unisex,” I reply, telling a white lie. “It looks good,” she decides. It’s hard to know what people think, just from their expression. There’s another complication, too. In most of the world, much of which is hot, men wearing airy garments over their legs are normal. Religious garments often have a dress-like form. It’s possible people are trying to work out if I’m wearing a jalabiya or jubba, even a sarong. I could be a funky cleric. I’m basically wearing a skirt with a get-out clause. It’s time to go bold.

Working it ... Rhik Samadder.
Working it … Rhik Samadder. Photograph: Alicia Canter/The Guardian

I return the linen number to Rowena, and we go shopping. In a charity shop, I’m drawn to a Lipsy animal-print number. “That’s a Wag prosecco dress,” demurs Rowena, who doesn’t believe in mincing words. “And not your pattern.” I pick up a paisley midi, in white and coral. Sweet, sort of 90s and fun. I buy it, but not everyone is sold. “Maybe we do this,” my friend says at home, whipping out some pins, and taking it up 25cm. She ties my T-shirt into a midriff-baring crop top. “Now that’s a look.”

I could wear this in the vicinity of an art school and blend right in. But where would the fun be in that? I take a trip to east London, to an old-school fruit and veg market. The traders stare, but no one tells me to put my plums away. Likewise, in a crowded greasy spoon. Some of the older clientele do look a little offended, which doesn’t feel good. I don’t want to upset anyone. But I’m only wearing a skirt. Men in shorts run topless wherever they like and no one bats an eyelid.

On public transport, no one says anything. Then again, you could wear a pillowcase like a chef’s toque and talk to a blancmange on a bus and no one would notice. In the street, there are more interactions. An elderly Chinese woman totters over to tell me I look good. I ask if the skirt is too short. “No. Nice,” she says. What a baller. (For what it’s worth, another elderly woman shouts “What the fuck is that?” in my direction.)

Young people are generally on board. “Slay,” smiles a teenage girl, shyly. There’s a fair bit of “Work it!” to balance out the disgust. Schoolboys are the worst, bless their suffering hearts, but most are simply curious.

I think gender roles are prisons, and we should all wear what we want. And I doubt I’m alone. I went to drama school, and would say roughly 100% of the boys were there so they could wear dresses. As a side note, I am conflating two different garments here. Is there more of a cultural template for “man in a dress” as opposed to a skirt? The aesthetic unity of dresses has always appealed to me, more than skirts. In any case, we yearn for the forbidden.

There could be another reason for the confused faces. It’s unseasonably cold, and raining. I’m not feeling pleasant airiness; the wind is whipping between my legs. Perhaps I just look chilly.

Other steep learning curves include knowing how to sit on public transport (place bag on knees, not between), thigh modesty, and where, in hell’s teeth, to put my things. It’s nothing if not a great lesson in empathy. Everyone should experience the exposure, scrutiny and restricted movement that skirt-wearers endure.

While weather is the most hostile force I encounter, I wouldn’t say men in skirts are normalised. “What the fuck is that?” is dehumanising language, not great for the old self-esteem. At first, I shrink. Then, I stand taller. Stare at me and I’ll stare right back. But defiance is tiring, and it saddens me that a man can’t wear a lovely piece of clothing without arming himself in this combative stance. I don’t have the energy for that every day. I can’t say what I’ll be wearing tomorrow, but I do know this: it’ll have goddamn pockets on it.

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