Switching to men’s clothing taught me that the world doesn’t want women to get too comfortable

A different look.
A different look.
Image: Reuters/Yves Herman
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For most of my life, I’ve worn clothing that leaves a mark. Bra straps nip at my shoulders; the backs of my shoes dig into my skin. Pantyhose leaves red rings around my stomach at the end of the day—glaring, and just as affecting, as felt-tip marks from a plastic surgeon.

Then, several months ago, I began wearing men’s clothing. Among the major advantages I’ve discovered so far: plentiful pockets, simpler dressing decisions, and easier temperature control. But the biggest revelation for me was the huge difference in my physical and emotional comfort. I’m a forthright, intellectual woman who’s never had a problem with confidence. But I’ve spent 20 years wearing clothes designed to make me feel ill at ease—in both my body and mind.

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Like a lot of women, I’ve long been accustomed to scrambling out of my clothes at the end of the workday as fast as possible. Being off-duty meant taking off my high heels, stripping off my tights, shedding knickers and anything with a waistband. After unbuttoning, unzipping, and peeling off my clothing, I’d breathe a huge sigh, signaling my physical and mental release. Yet despite this nightly ritual, I usually took the discomfort and constrictions of women’s clothing for granted.

Nor did I consider its chafing effects on my mind. A lot of my clothing never quite fit me—instead, I had to make sure I fit it. Wearing an off-shoulder shirt or a silk dress meant constant fidgeting and adjusting. Every mirror, shop window, or reflective surface was an opportunity to check my appearance; every glimpse was a disappointment. The threat of gaping, riding up, and puckering was ever-present.

And because women’s clothing gets more complicated and fussy in accordance with the formality of the occasion—think stilettos and backless dresses—my anxiety increased in direct correlation to the importance of the event. The background buzz of clothing-awareness has been the backdrop to every big event I can remember attending, from weddings to job interviews to first dates. It sickens me, remembering just how self-conscious I’ve been about my clothing at the exact moments when my attention should have been directed elsewhere. Now that my eyes are opened to it, I see this discomfort everywhere—women hobbling, hitching, fiddling, and smoothing, while men go peacefully about their business.

I can’t say that I’m always comfortable now that I wear men’s clothing, especially as my hallmark is a tie (although I never do it up to the point where I can feel it). But I cannot understate the net effect of wearing clothing that is looser, more flowing, and cut for comfort, without sacrificing formality and professionalism.

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I still mix elements of traditional femininity into my wardrobe; I curl my hair and wear lipstick. But one of the best things about shirts, waistcoats, and trousers cut for men is the way the clothing is designed to cover, not accentuate. The lines are straight and clean. And while I still have plenty of junk in my trunk (I’m a size 38D and UK 14), no particular part of my body is the most visible thing about me any more. More to the point, my body is not the most salient thing on my own mind these days—and that’s an incredible relief.

That said, I’m still getting used to dressing for comfort. My greatest challenge so far has been packing for holidays—specifically, what to wear to the beach.

Let’s be clear: I’m generally at ease with my body. I’ve been several stone thinner and I know that it doesn’t make me happier; I’ve had two children, and I don’t care about my saggy bits. But no matter how confident you are, beachwear often presents a challenge. The parts of you that are usually hidden from sight are on display. It’s incredibly difficult to feel free and easy under those conditions, even when you’re supposed to be relaxing.

Since trying menswear, my general rule has been to only wear clothing that feels comfortable and allows me to make my own choices about how much of my body to draw attention to. Swimwear, for both genders, pretty much blows this rule out of the water. The closest clothing I can find that’s in accordance with my principles is a legsuit, a high-necked, one-piece suit that goes down to my mid-thighs.

The legsuit has some advantages compared to most women’s swimwear: it requires no shaving, exposes no butt cheeks, and has enough support that there’s a decent chance my breasts will actually stay contained when I dive into the waves. But every contour of my body is still pretty much visible, albeit under a layer of lycra.

Recently, while packing for vacation, I found that thoughts of swimwear had me slipping into old habits. I worried over what else to put in the suitcase. Tops and bottoms had to be coordinated; comfortable yet complementary shoes considered; and what about socks, tights, and bras? Even though I’d largely given up women’s clothing, clearly, women’s fashion had left a mark that was hard to scrub off.

Then I paused and looked over at what my boyfriend was packing: a pair of shorts, a pair of jeans; a few T-shirts, a few button-downs. Just one pair of shoes. He wasn’t exerting mental energy trying to imagine how fellow vacationers would perceive him and his body; he was just bringing the clothing he needed to enjoy his holiday.

With that, I tossed a few of my own T-shirts in the suitcase and zipped it shut. Dressing comfortably isn’t just a matter of finding breathable, well-cut clothes—it’s also a mindset.