Is Crossdressing Becoming More Popular?

Or Just More Visible?

Every so often, someone will ask, usually with a raised eyebrow and a tone somewhere between curiosity and concern, whether crossdressing is suddenly “on the rise,” particularly among younger men.

It’s a fair question. Walk through certain corners of social media, browse fashion editorials, or spend ten minutes people-watching in the right urban neighborhood, and it can feel like something has shifted. The old lines, once thick, permanent, and aggressively enforced, now look faint, negotiable, even optional.

But before declaring a full-blown trend, it’s worth slowing down. What we’re witnessing is not quite what it seems. Because the real story isn’t that crossdressing has exploded. It’s that the silence around it has.

For decades, men who wore feminine clothing existed in a kind of cultural shadow. Some did it privately, some occasionally, some as part of a deeper identity, and some simply because they liked how it looked or felt. What they shared was not necessarily motivation, but invisibility. Social cost kept things quiet. You didn’t see it because people made sure you didn’t.

That pressure hasn’t vanished, but it has weakened. And when pressure eases, visibility rises.

Younger men, in particular, are growing up in a different atmosphere. They’ve inherited a culture where gender rules are no longer handed down as commandments but offered more like suggestions. Try this. Don’t try that. See what fits. Ignore what doesn’t.

That doesn’t mean they’re all crossdressing. Far from it. Most aren’t. But more of them are willing to experiment... once, occasionally, or in specific contexts without assuming it defines their entire identity. A skirt might be a fashion choice. Makeup might be aesthetic. Presentation might be fluid, situational, or even playful.

And that’s where the confusion creeps in.

We tend to collapse everything into one category: crossdressing, identity, lifestyle, orientation, as if they’re interchangeable. They’re not. A young man trying on a different presentation for a night out is not necessarily making a broader statement about who he is. He may be. Or he may just be trying something on, in the most literal sense.

What’s new is not the behavior itself. It’s the permission.

Of course, it’s not universal. Geography still matters. So do family, workplace, and social circles. In some places, the old rules remain firmly in place, and stepping outside them still carries real consequences. Even where acceptance is higher, there’s often an unspoken line between what is “edgy but acceptable” and what crosses into discomfort.

So no, we’re not looking at a tidal wave of young men abandoning traditional dress overnight. What we are seeing is something quieter and, in its own way, more significant.

A gradual loosening. A willingness to question what used to be unquestionable. A shift from “never” to “maybe,” and in some cases, to “why not?”

And once that shift happens, even a small number of visible examples can feel like a cultural surge. But it isn’t a surge. It’s a reveal. The men were always there. They’re just harder to ignore now.

And so it goes.

Wearing Alice + Olivia

John Hurt femulating in the 1975 British film The Naked Civil Servant.

In Touch

It started, as these things often do, with something small and entirely deniable.

“Just curiosity,” said Frank, holding up a tube of tinted lip balm in the pharmacy aisle like it was evidence in a trial. “Practical, really. Winter dryness.”

His wife, Carol, didn’t even look up from comparing two brands of moisturizer. “Of course. Hydration is important.”

That was a Tuesday.

By Friday, Frank had “accidentally” discovered that Carol’s cardigan was “surprisingly comfortable.” By Sunday, he had opinions about fabric drape. And by the following week, he was standing in front of the bedroom mirror, turning slightly to the left and then the right, asking a question no man in his bowling league had ever asked out loud:

“Does this color wash me out?”

Carol, to her credit, adapted quickly. Some spouses resist change. Carol organized it.

“Well,” she said, arms folded, evaluating him with the same calm authority she once used to choose kitchen appliances, “if you’re going to do this, we’re going to do it properly.”

That was how Frank found himself booked for a “consultation.”

---

The salon had a name that suggested both luxury and inevitability: Refinement.

Inside, a row of men, formerly known as guys, sat in plush chairs, each at a different stage of what could only be described as… progress.

One was having his eyebrows shaped with the solemn intensity of a sculptor restoring a Renaissance statue. Another was being fitted for something that involved boning, lacing, and a level of commitment Frank had not anticipated.

Frank swallowed. “I thought maybe we’d start with… a scarf.”

Carol smiled. “We are starting with a scarf.”

Two hours later, Frank emerged with a softly layered haircut, a light application of makeup, and a scarf tied in a way that suggested he had opinions about art galleries.

He looked… good.

Annoyingly good.

---

The shift spread faster than anyone expected.

At the office, it began with small changes. A bit of moisturizer here. A neater haircut there. Then came the cardigans. Then the shoes.

Within a month, Casual Friday had been replaced by what HR cautiously called “Expressive Presentation Day.”

Frank, now frequently referred to by Carol as “Frances, when he’s making an effort,” found himself mentoring younger men.

“You’re rushing it,” he told Kevin from accounting, who had shown up in a dress that clearly had not been chosen with his proportions in mind. “You need structure. And better shoes. Those are… optimistic.”

Kevin nodded solemnly. “I thought the heels were the point.”

“They are,” Frank said. “But not like that.”

---

Meanwhile, the women adapted in their own way.

Carol bought three new pantsuits. Not because she needed them, but because she enjoyed the symbolism.

At social gatherings, the dynamic had shifted so completely that no one even mentioned it anymore.

Wives stood in small, confident clusters, discussing careers, investments, and travel plans.

Their husbands, now softer, neater, more… considered, stood nearby, comparing fabrics, adjusting accessories, and occasionally asking each other, in hushed but earnest tones:

“Be honest. Is this too much?”

---

The real turning point came at a neighborhood party.

Frank arrived in a tailored skirt suit, understated but precise, with a small brooch Carol had insisted on.

As he stepped into the room, there was a brief pause… the kind that used to happen when someone broke a social rule.

But now?

A nod.

A smile.

A quiet, collective acknowledgment: Yes. That works.

Carol slipped her arm through his. “You clean up well.”

Frank exhaled, just slightly. “I was going for… put together.”

“You succeeded.”

Across the room, Kevin from accounting was explaining pleats to someone who looked deeply overwhelmed.

Progress.

---

Later that evening, as they walked home, Frank adjusted his scarf against the cool air.

“You know,” he said, “I didn’t expect it to feel like this.”

“Like what?”

He thought for a moment.

“Like I’ve been underdressed my whole life.”

Carol laughed, not unkindly. “Most of you were.”

He glanced at her. “And you’re okay with all this?”

She considered the question, then gave a small, satisfied nod.

“Oh, I’m more than okay with it,” she said. “I’ve been waiting years for you all to catch up.”

Frank looked down at his high heels, good shoes, he now knew, and then back up the street, where a few other couples walked ahead, the silhouettes just slightly different than they used to be.

“Funny,” he said. “All it took was getting in touch with our feminine side.”

Carol squeezed his arm.

“And a little guidance,” she said.

Wearing Boston Proper

John Hansen (center) femulating in the 1970 film The Christine Jorgensen Story.

Downsides of Crossdressing

Pammy asked, “Are there any downsides to crossdressing?”

If you’re asking honestly, then yes, there are downsides. It’s better to look at them clearly rather than pretend it’s all upside. Whether those downsides matter depends on the individual, the situation, and how it’s handled.

Here are the areas where things can get complicated:

Social consequences are the biggest factor. While attitudes have improved, negative reactions still exist especially in more conservative environments. In some workplaces or communities, being “outed” can create real problems. Partners, friends, or family members may struggle to understand or accept it. It may not be fair, but it is reality. You have to decide how much visibility you’re willing to risk.

Relationships can also be affected. Crossdressing can introduce confusion, insecurity, or mismatched expectations between partners. One person may see it as occasional expression, while the other sees it as something much more significant. Secrecy tends to make things worse if it’s hidden, it often damages trust. The hard truth: avoiding honesty early on usually leads to bigger problems later.

Emotional patterns are another area to watch. For some, it’s not always harmless fun. Cycles of enjoyment followed by guilt can develop. There can be a tendency toward escalation, that is, needing “more” over time to achieve the same satisfaction. Others may experience uncertainty about what it means for their identity. This is where self-awareness matters. If it starts controlling you instead of the other way around, that’s a red flag.

Financial cost is easy to underestimate. Clothing, shoes, wigs, and makeup add up quickly. Maintaining multiple wardrobes can become expensive, and trial-and-error purchases often mean wasted money. Without discipline, it turns into a quiet but persistent drain.

Safety concerns depend heavily on where and how you present. Public harassment, uncomfortable confrontations, or vulnerability in unfamiliar environments are real risks. Online exposure can also lead to ridicule or doxxing. Situational awareness isn’t optional—it’s necessary.

Time and energy can become significant. Grooming, dressing, and makeup take effort. Add in planning, logistics, or secrecy, and it can consume more mental space than expected. Like any hobby, it can crowd out other priorities if left unchecked.

For some, but not everyone, it can become habit-forming or compulsive, especially if it’s tied to stress relief. If it starts to feel like something you have to do rather than something you choose to do, that’s worth paying attention to.

Bottom line: crossdressing itself isn’t inherently bad. The downsides come from how it fits into your life, how honest you are about it, and whether you’re in control of it…or it’s in control of you.

If you keep it intentional, grounded, and integrated with the rest of your life, most of these risks can be managed. But if it becomes secretive, compulsive, or starts colliding with your relationships and responsibilities, that’s when the real costs show up.

Wearing Boston Proper

Bruce Watson femulating in an episode of television’s Charlie's Angels, 1981.

Dressing for the Weekend

Men Being woMenly

Choices

We make choices everyday.

(Boxers, briefs or panties? Yogurt or bagel? Bra or bra-less? Regular or decaf?)

Some choices are more important than others and some have long-term ramifications.

(Should I be a doctor, a lawyer or a fire chief? Should I marry her, him or it?)

Sometimes our choices backfire. Sometimes our choices are just plain wrong and we suffer the consequences, but we are still free to choose whatever we want.

So why can’t we choose our gender?

Despite all the scientific evidence to the contrary, the anti-transgender crowd claims that transgender folks choose to be transgender just like the anti-gay crowd claims that gay folks choose to be gay. And according to those crowds, making those choices is wrong.

I am naturally feminine. My feminine speech and mannerisms are a bad fit in boy mode, but in girl mode, they are a perfect fit.

I could man up and never wear a dress again, but I chose not to impersonate a male. So, yes, I made a choice to live authentically and not fit in with the boys.

But what if I was not transgender?

What if I was a guy with no gender issues, who carefully weighed all the options and decided that living my life as a woman was preferable to living my life as a man. And as a result, chose to live life as a woman.

What's wrong with that?

I say, “Absolutely nothing.”

It is just another choice. Admittedly, it is a big choice with a lot of long-term ramifications, but humans make important choices everyday. That’s why God gave us intelligence and free will ― so that we can make choices ― like choosing our gender.

Wearing Bebe

Patrick Walshe McBride femulating on British television’s Shakespeare & Hathaway: Private Investigators.

Someday Funnies

Wearing ModCloth

Rachel out and about in a sports bar.

Six Months Left to do Your Christmas Shopping

 

Wearing Boston Proper

Vincent McDoom

Stuff: Thoughts from Abroad

By J.J. Atwell

Abroad?

Did you think this was going to be about me referring to myself as “a broad?” Sorry to disappoint. Instead, I’d like to relate some observations from a recent trip abroad – observations about women’s styles of course. 

There is a Different Aesthetic

My trip included England and Norway. A couple of places that are similar, but very different. I’d also allow that the places I visited were more touristy, but did include some regular locations, with regular people, as well. 

Perhaps the most interesting thing I noticed was that the professional women I saw were frequently wearing skirts and hose – very stylish outfits for sure. The fact that they were wearing hose was the odd thing for me. You see, JJ lives in the south where the temperatures are pretty high. So we seldom see women wearing hose. It’s just too hot for that. But I understand the bare leg look is not uncommon at all even in the big northern cities in the USA. 

As an aside, when getting ready for one of JJ’s group meetings, I went looking for some dark pantyhose. It wasn’t an easy search. There were few options available here where the weather is hot almost all the time. It seems like here in the USA that the regularity of women wearing hose is fading away. Perhaps, Europe is behind the curve here.

Other Differences?

Yes, I noticed interesting styles. Especially in Norway where much of what was for sale was targeted more to the colder climates. Not surprising, you say. Well yes, except that the weather while we were there was in the upper 70’s and low 80’s. So obviously there should be a market for some lighter wear. Also, lots of clothing in Norway were knitted with interesting, intricate patterns. 

Sizes are also a bit different. It seems that it’s hard to find things in larger sizes when abroad. Marked sizes are only an indication of what the garment might be. In the US we often hear the term “Vanity Sizing.” That’s the practice of making clothing larger than the standard size or marking it one size smaller. That way people can proudly say they are a size 8 when in reality they are a 10. Or a 12. 

I noticed however that sizing in Norway especially seems to run pretty small. An XL size there might be equivalent to a M or L in the US. If you go shopping abroad be sure to hold up the clothing to get a better idea if it will actually fit. 

I’ll admit that most of the women I noticed were younger and perhaps my impressions are just my old, male bias showing through. But I did come away from the trip with a different perspective on style abroad. Maybe it is simply differences in the environment or climate in the places I visited. People adapt their clothing to suit where they live. 

I’ll Be Back

I’ll be back with more Stuff in the next installment. Comments are welcome either here on the blog or by email to Jenn6nov at-sign gmail dot com. JJ is always looking for more stuff so let me know what you would like to read about.

Wearing Nine West

Sture Lagerwall femulating in the 1934 Swedish film Adventures At The Hotel
(Äventyr på hotell).