Ask AI

[Barleymower]

Personally I don't take AI too seriously, it generally is quite good at summarising a google search. So while doing a MIS search on the web this AI review of the question popped up. More interesting than what AI had to say were the the comments (read them at the end)

Before we all start booing AI, here's what it had to say:

I asked an AI to explore what society would be like if men could wear womenswear as freely as women wear menswear today. Here is its response.

If men wearing womenswear were as socially acceptable as women wearing menswear, the change wouldn’t be loud or revolutionary—it would be quiet, structural, and deeply normalizing. The most important shift wouldn’t be clothing itself, but what clothing would stop signaling.

Below is what that society would likely look like, step by step.

1. Clothing would lose its moral charge
Today, womenswear on men is still read as transgressive—sexual, comedic, political, or identity-defining. In a normalized society, that interpretation collapses.

A man in a skirt would register the way a woman in trousers does now: a style choice, not a statement.
No automatic assumptions about sexuality, gender identity, or psychology.
The question wouldn’t be “why is he wearing that?” but “is it appropriate for the weather or setting?”

This mirrors what happened when women adopted suits, jeans, and workwear: the shock faded, the meaning drained away.

2. Masculinity would become less brittle

Right now, masculinity is fragile because it is defined by exclusion—what men must not do, wear, or enjoy.

If menswear and womenswear fully overlapped:

Masculinity would shift from policing appearance to describing behavior and character.
Men would no longer need visual armor (uniforms of toughness) to be taken seriously.
Emotional expressiveness and aesthetic interest would feel less risky.

In short: masculinity wouldn’t disappear—it would relax.

3. Professional life would quietly adapt

The workplace is where this normalization would matter most.

Office dress codes would pivot from gendered rules to function-based standards (formality, safety, branding).
A man in a blouse or skirt would be judged on performance, not “credibility.”
Power dressing would diversify: authority would no longer be tied to a narrow male silhouette.

This would echo how women once had to dress “like men” to be taken seriously—except now, seriousness wouldn’t depend on gender mimicry at all.

4. Fashion would become more innovative—and more boring

Paradoxically, acceptance produces both creativity and ordinariness.

Designers would stop marketing womenswear-for-men as edgy or subversive.
Retail would reorganize around body shape, fit, and style, not gender labels.
Many men would experiment briefly—and then settle into very normal looks.

Just as most women didn’t start wearing tuxedos daily once allowed, most men wouldn’t suddenly live in gowns. Normalization reduces spectacle.

5. Social anxiety around gender would drop

A major driver of modern gender conflict is symbolic panic—the fear that visible change equals social collapse.

In a society where clothing crossover is settled:

Parents wouldn’t panic over sons in dresses any more than daughters in pants.
Media outrage cycles would lose fuel.
Gender expression would feel less like a battlefield and more like a spectrum of taste.

When symbols stop being forbidden, they stop being powerful.

6. Relationships would rebalance subtly

Heterosexual, gay, and queer relationships would all shift—but quietly.

Straight men would feel less pressure to perform dominance through appearance.
Partners could negotiate attraction more honestly, without rigid scripts.
Power dynamics would rely more on economics, personality, and emotional labor—not visual gender cues.

Importantly: attraction wouldn’t vanish or homogenize. It would individualize.

7. What wouldn’t happen (common fears)

It’s worth being blunt about this.

Men would not “become women.”
Gender would not disappear.
Society would not lose structure or coherence.
Most people would still dress conventionally most of the time.

What would disappear is the idea that clothing is a reliable shorthand for worth, strength, or legitimacy.

Bottom line

A society where men can wear womenswear as freely as women wear menswear would not be chaotic or radical. It would be less anxious.

Less symbolic panic.

Less fragile masculinity.

Less obsession with policing appearances.

And more room for people—men included—to exist without constantly proving what they are not.


The comments:

I wonder what would happen with women who are totally accepting of men wearing feminine attire, but not their man? Would that shift, too?
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I somewhat disagree about womenswear on men. I believe all clothing is gendered by being sexualized. Even when women wear menswear designed for women, it still retains tailoring notions and trimmings to attract attention to the wearer and perhaps highlight a female's specific charms (breasts, waist, hips, legs etc.). Think of a tailored pantsuit highlighting a woman's figure and embellished with subtle do-dads to draw the eye there. Men's clothing does not; another reason why it is so plain. A dress on a man in this case would be merely a toga, or a skirt would be a kilt.
It is only my opinion folks and I look forward to the discussion....or, heaven forbid, the end of crossdressing as we now know it.
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I've seen women wearing clothing inspired by menswear, yeah, they look terrific. I've also seen women wearing menswear and they look somewhat incongruent. Bulges in wrong places, no contour to the chest due to binders, etc..There are definitely FTM people out there and I think they are just as maligned as MTF folks.
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And perhaps one of the weaknesses of AI - its difficulty to 'think' philosophically - has been laid bare in this post. Because if we create a world where clothing no longer demarcates gender, then the clothing loses its symbolism. This is exemplified by the simple denim jean - the only thing that determines which sex a pair is for is the nuance of the cut to take account of body shape. Otherwise they are no longer seen as the sole preserve of one or other of the sexes.

And kilts are another example of this, albeit from a different perspective. They give legitimacy to men wearing skirts and whereas the word 'skirt' still has gender connotations, the word 'kilt' does not and it's only the cut (and perhaps the addition of a sporran) that provides the demarcation.

So in the world described by this post, do the terms 'menswear' and 'womenswear' become irrelevant or do they just become a means of describing the structure - i.e. the cut - of a garment and no longer have a bearing on style?

And where does that leave us? Crossdressing relies on a clear distinction between what women wear and what men wear. If that distinction disappears, would the freedom to wear what we want fulfil us or just render our whole world irrelevant? You titled the post ‘When Men Dressing Like Women Stops Matter¬ing’ but for female to male ‘crossdressers’, that day has already arrived but if we see such a person, do we look at them as wearing men’s clothes or just gender neutral ones? And if we encounter an unashamedly feminine woman wearing a three piece suit and tie, do we process that as ‘she’s wearing men’s clothes’ or just ‘she looks amazing?’

In the end, for it not to matter, we have to decouple gender from clothing which, in turn, makes the basic premise irrelevant.
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Very interesting AI post Stana - well done for acknowledging & posting. It is my belief that women, including wives (!) will fully accept men dressing as women at a future point that is nearer than a lot think. Rate of change/acceptance has accelerated at a staggering rate.
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What it fails to mention, though, is that we have already been down this road before with no adverse consequences if one just looks at the gender-bending, over-the-top fashions of the 1600's and 1700's...and even going back to Roman times (and the like) when both sexes wore unisex toga-like clothing. Which begs the question "where did society go wrong" in this regard?
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I do not think AI has the answer. Over the centuries clothing has moved to and fro with regard to which gender dons various items. As far as acceptance for men to wear women's clothes, my wife has a wide tolerance for that, as long as it's not me. I wouldn't be surprised if many women have that attitude.
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Whenever I read articles that discuss a world where men can freely wear women's clothes, I always wonder how many will and what types of clothes. Will we see men in the office in skirts and heels and hose? Strolling the boardwalk in a sundress? Dancing in a sparkly dress and stilettos on a Friday night? Meeting friends at a coffee shop in a sweaterdress and tights?
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Interesting points made by AI, but I think it was the wrong question that was asked. Men CAN wear what are classed as women's gendered clothing and many men do including myself as a skirt wearer. I believe it's only men's social conditioning stemming from childhood, that stop themselves from wearing, and freely expressing themselves as they wish like women do. There are some nuances of course. Women's clothes have been somewhat sexualised over time, and there is still a social norm that men who wear women's clothes should fully crossdress to masquerade as women, which complicates the issue a little, but a man can still wear a skirt and a man's top, feel comfortable doing so and not send out a confusing message, he is still clearly just a guy in a skirt.

[Modoc]

I pretty much agree with Ai's conclusions, but still, the issue remains: how do we get to that place from where we are now?
I do hope that such a glimpse at the potential serves to embolden more to strive towards that future. Short of there being some sort of great awakening, the only hope I see is that every man who wants to make the change do it now to the degree that he can. It will never happen as long as we sit around and hope and wait for some kind of instant societal reset to take place.

[Barleymower]

Men are too scared to try it.
Looking at it another way, if you are bold and go out there yourself, you are a highly individual guy doing something that most other men haven't got the nerve to do themselves.

[brionacmkw]

I don't think most men even think of skirts as an option due to social conditioning. I'm not sure exactly how we get to the place where it is fully accepted. Representation is important so of course the more it is seen in the public eye the better

[Barleymower]

I don't think most men even think of skirts as an option due to social conditioning. I'm not sure exactly how we get to the place where it is fully accepted. Representation is important so of course the more it is seen in the public eye the better

That's why it's important that we get out there.

[Grok]

I suspect that the scenario that opened this thread is a long, long way off. Almost certainly beyond the lifespan of anyone posting to this forum.

[FLbreezy]

In the current state of affairs, the term "gender neutral" is such a big misrepresentation. It almost universally means "clothes for women who want to dress like men."

[Grok]

It almost universally means "clothes for women who want to dress like men."

Yes, and much the same for Unisex.

[Barleymower]

Luckily here in the UK we can wear skirts and nothing out of the ordinary will happen. Men wearing skirts is here and more and more men are doing it.

[Uncle Al]

May I make a request

Several years ago, the A. I. subject came up and a few "newbies" to the Cafe' thought my screen
name was an A. I. 'bot' not AL(upper case L vs lower case l) as in a real person. These newbies
had PM's with Carl and he set them straight, that I was a real person.

So, PLEASE - PLEASE, when discussing Artificial Intelligence, use a period (.) after each letter, to avoid
any further confusion.

Thanking you in advance

Uncle Al

[Modoc]

So, PLEASE - PLEASE, when discussing Artificial Intelligence, use a period (.) after each letter, to avoid
any further confusion.

Thanking you in advance

Uncle Al

Hey Al, no disrespect intended, but billions of people worldwide are familiar with" Al" being the most recognizable acronym for artificial intelligence.
I will respect your request, of course, but most people here, and certainly any newcomers to the site, who don't look into this thread, will not be aware of it. Unless there is some way to make it your wishes apparent to all who enter here, you can expect many occurrences of people using what they believe is the universally accepted designation for artificial intelligence.
Just saying.

[Uncle Al]

Hey Al, no disrespect intended, but billions of people worldwide are familiar with" Al" being the most recognizable acronym for artificial intelligence.
I will respect your request, of course, but most people here, and certainly any newcomers to the site, who don't look into this thread, will not be aware of it.

Thanks Modoc. I know this may sound trivial but each time I see the thread title,
I read AL instead of AI. I just don't want to be confused with an Artificial Intelligence.
Artificial I'm not, Intelligence - is questionable


Uncle AL


(Guess I'll switch from a lower case l to upper case L in my signature )

[skirted84]

AI is what most on here want. A utopian view of normality and unremarkableness. Uninhibited choice for both men and women.

Back in the real world, men feel they have too much to lose. Change is happening too slowly to expect this in my lifetime.

[Barleymower]

AI is what most on here want. A utopian view of normality and unremarkableness. Uninhibited choice for both men and women.

Back in the real world, men feel they have too much to lose. Change is happening too slowly to expect this in my lifetime.

Not exactly utopian, AI predicts "ordinariness...
Many men would experiment briefly—and then settle into very normal looks".

Which makes me think we are already living in the best time. Innovation. Individual, risky, bold, adventurous. All those things right now.