What dictates what men and women should wear, or how they should act, or which body parts are indecent when exposed in the public, are all pretty arbitrary. Maybe they had some genetic or evolutionary roots, but they're largely irrelevant. Pink used to be seen as manly and blue seemed more dainty and thus were more suitable for girls. Today it's the reverse, which shows just how arbitrary and malleable our opinions are on these things. It's malleable, but not perfectly so. For example, it took women having to chip in for the war effort at home while men bled abroad in order to break through the gender role of the woman staying at home and taking care of the kids. This, along with other movements, helped make it socially acceptable for woman to be the caretaker or a breadwinner.
Reason 1: Lack of social movements for males to have the freedom to be themselves.
Men on the other hand did not have a social revolution to change things around. Yes, it was more convenient for the women to get their social change than the men for men to be able to do girly things, but I don't think that's a good enough excuse. Arguably men have been wimps in trying to get social change on their side too. It's a privilege women have that men do not, and one of the events that got the ball rolling/rolling faster was also due to female privilege: Not having to die out there. Since men's clothing are more utilitarian, the only other three reasons for dressing up as a female are: 1) Fetish 2) Transgender 3) Fashion. And in all three cases the public has one thing to say: Ew. How many men want their reputation to die on this hill by trying to start a movement for men for women's clothing? Besides, when a man brings up male issues they are seen as privileged folk who are anti-female-folk. Who wants to work out issues if that's the case? Sometimes it's hard to bring up issues men have without people trying to compare it to women's issues and declaring that men's issues are lesser and they should just suck it up.
Women used to have rigid roles and behaviors but that changed. That's good.
Reason 1a: Rigid gender roles for males.
Men are locked into a masculine role and it's hard to get out. In middle school I remember when a male said he loved a friend he had to say 'I love you! ...No homo'. Yes, anti-homosexual sentiment was more common back then, but this kind of talk really only happened when a male was talking to another male. Why? Because they were stuck in masculine social roles.
This means being a manly, testosterone driven man. This man doesn't take shit from anybody. He liked girls and only girls. He sucks it up when shit happens, and never cries. He doesn't need emotional support.
This is how you end up with overly aggressive men that end up fucking up their lives. This is how you get homophobia, but only for male homosexuality while female homosexuality was fine. This is how males have a higher rate of successful suicides compared to the higher rate of suicide attempts by women. (My assumption is that women aren't too stupid to commit suicide properly, but rather some attempts are cries for help whereas men who attempt are actually done with the world.) You get higher risk taking and more risky behavior leading to more deaths. And more time in jail. The population of people in prison does not mirror the proportion of men vs women in the general population. To that I don't say the judicial system is biased against males (which may be the case), I just highlight the fact that men commit more crimes. Yes, I call out the guys when I think it's time.
To summarize this point: It's not about women being inferior. It's about men not having the freedom to be anything but men due to a dent of history.
Reason 2: It is seen as a sexual perversion.
I'm the type of person that says gender roles hurt men and women, and men and women are different and act differently, but should be given the freedom to be themselves. So when I say women want this and this, I'm also going to say men act in a certain way too that's not desirable for which women are off the hook entirely. Men have higher sex drives and have a higher chance of having a crossdressing fetish. Some people will see men who crossdress as creepy men with an exhibitionist fetish trying to showcase their fetish to the entire world. Have you seen a sissy fetish forum? Maybe it's best if you haven't. There is no female counterpart to this.
Men can just simply be more creepy. Most sexual crimes are committed by males. Males are physically stronger, so if a man wants to rape somebody they are more likely to get their way than vice versa. It makes sense for women to be more worried about men than vice versa. When somebody dresses differently and people think it might be sexual, then that sets off many warning bells. This man is dangerous! (And if the man looks ridiculous then doubly so.)
Reason 2a: Men's clothing are more utilitarian.
Because men's clothing are more utilitarian, men can't use that excuse for dressing up like a girl. It takes more effort for a man to present as a woman than a woman to present as a passable man that blends in. A man that dresses up as a woman either makes no effort (in which case he sticks out like a sore thumb from a mile away) or makes lots of effort (what is he hiding? why does he want to look like something he's not so badly? Does he want to rape my children?). Whereas, if a woman wants to wear guy's jeans she just says that she gets pockets now and she wants to look 'professional'. Baggy sweatpants and sweatshirts are already utilitarian, so how much of a leap is that to some men's jeans?
You can imagine the man wearing makeup poorly, wearing a bra when obviously it has no utility to him. People are going to think bad things about him.
Reason 2b: Women's clothing are more form-fitting.
Women's clothing tend to be more form-fitting and skimpy (or sexual) than male clothing. If a male has an ugly and hairy male body, then it looks ridiculous. If a lot of men just decided to wear women's clothes all of a sudden, it would be normalized and okay. But they won't. Our tastes for what looks good are probably far more malleable than we give it credit for. Most women actively leave men who dress like a girl. They're disgusted... because today we think men who dress like a girl without making a serious effort look creepy as fuck. That's an aesthetics thing, not a sexism/power thing. If it was about men degrading themselves and losing power by subjecting themselves to a weak feminine role, the emotions against male crossdressers would not be that of disgust for how they look aesthetically, but rather anger and disappointment. Ask random people why a man in a dress is bad, and they will say it's sick (perverted) and disgusting.
Another Reason
Another reason is that femininity is seen as inferior and masculinity is seen as superior. Some people argue this point by saying that it's okay for women to wear men's clothing because they are seen as striving to be something better (masculine). Then some people turn around and argue that when women try to be assertive, they are seen as overly pushy and thus are viewed negatively. Which is it, do men like it when women try to be more masculine or not? You can't have it both ways.
Some point to the fact that masculine jobs tend to pay more than feminine jobs to try to prove femininity is seen as inferior. This makes no sense; the corporate world wants people who are willing to be a hollow breadwinner who ignores social life as they work up the food chain. This has real sacrifices. The sciences pay more because our smarts are what differentiated us from the other animals, and what will improve technology for the future. This isn't some well-crafted, super deep conspiracy to subdue women so men have all the power.
When people encourage women to join STEM fields, that too is not the patriarchy showing. Ironically some call this out as evidence that femininity is seen as inferior even though these policies are often championed by the feminist left. And I more or less agree with that line of thinking anyways: Praise the benefits of a STEM job. There might be workplace discrimination and part of that is due to quotas, giving women jobs because they are women (a blatant discrimination against men and the hours they've put in, along with promoting under-qualified people to jobs). But the other part might just be due to men being used to working with just men. If I had to go look for sexist men I'm sure I can find some. These are all factors, but I don't think any of them screams 'the society at large things femininity is inferior'.
If you consider feminine traits to be things like kindness, nurturing, daintiness, attention to aesthetics, being pretty, and graceful, you run counter to traits like ruthless, cold, calculating, dog-eats-dog corporate world. In that sense yes, femininity IS inferior in that environment. Femininity IS weaker. You may not want to include the traits you don't like associated with femininity, but historically that is what we think of when we think of femininity. But just because femininity might be inferior in a corporate setting doesn't make it actually inferior. If you judge a fish by its ability to climb a tree you're going to think all fishes are morons. There is a time and place for femininity and a time and place for masculinity. Men and women can learn from each other.
We're getting getting steps removed from the actual issue. This is because people are trying to wedge their identity politics into an issue where it doesn't really belong, and to do that you have to make contrived arguments that are several steps removed from the issue. You can see how this is a problem conversationally: I come up with reasons why male to female crossdressing is frowned upon that are to the point and hard to argue with, and somebody else comes in and brings in the entire feminism/patriarchy baggage. What am I supposed to do, disprove their feminist theory on the spot or accept they are right? On a conversational level it's a nightmare. It's a tragedy too, because a subreddit dedicated to transgender issues is supposed to be a place of support (it is even enshrined in the rules). Yet if I bring up an opinion contrary to the prevailing feminist leftist ideas, I get called out every time. And the way they make their point just encourages people who disagree to get sucked into a drawn out, irrelevant, and exhausting argument about feminism... which is not what I set out to discuss.
The Problem
The problem with many feminists is that they don't just pick from a table of ideas based on what they think is right. They pick feminism and identify with it, such that critiquing feminism becomes personal. They see the world through a feminist lens. When you have a hammer everything looks like nails. When you know what the problem is a second into the conversation (misogyny) and the solution (yelling about it online), what need is there to think any further about the topic? I repeat: Running straight for the feminist argument has caused people to stop thinking any further. This is why this example is such a perfect case study for when identity politics and the feminist lens causes people to be myopic. They don't even try to think about other reasons why crossdressing one way is more socially acceptable than the other way around. Not once in the entire Reddit thread did anybody say 'it could be misogyny, AND something else'. No, it's ALWAYS misogyny and NEVER anything else. I think one hidden reason is that having a problem have more than one cause probably makes their feminist agenda seem less urgent, so there is no room for more than one cause.
Identity politics is how I got 'called out' for calling a girl a cunt who was clearly being a cunt. But had I called her a dick, it would've been fine. It's rude when it's a female body part, but when it's a guy's body part we're discussing, who cares? This is how people turn male problems into somehow women getting oppressed. To be honest, it really looks like mental gymnastics to me to go from A and get to Z. With enough effort almost anything can be about women being oppressed. But am I stretching my ideology to fit and explain something because I'm attached to it, or am I invoking it because it is the more logical and parsimonious explanation? Are women actually seen as objects and thus are not capable of being a pervert, or are men actually just more likely to be perverts and to commit perverted crimes (statistical fact)? If women are just objects then they should be barred from all jobs right now.
Feminists often get angry when other people question the veracity their experiences. I've had somebody accuse me of accusing other women of lying about their experiences, when in fact I typically just wonder if a situation is being interpreted correctly. A Republican and a Democrat can watch the same political speech and come away with very different conclusions. So it is striking when leftist feminists discount the experiences of male to female transgender women when they were living as a guy. Oh, they felt being a guy was limiting because they are transgender. There's something insidious about using one's transgender identity as an argument against them in this way. They'll probably come after my experiences next and say those aren't valid too.
And that's the question: If it were the reverse, what would happen? If a trans woman had said even living as a guy he felt he was super privileged, the feminists would take that as evidence that men are privileged. If it's the reverse, their experiences are invalid because they dislike their gender role as male because they were transgender. Let's try another one: If men could wear women's clothing but women couldn't wear men's clothing, would that falsify my ideas? Yes, so my ideas are falsifiable. Would the feminists in that subreddit feel that would falsify their ideas? Absolutely not. They would say that men are superior and women are prevented from reaching the top levels of society, so they are not worthy of being masculine and must remain as poor, subservient individuals. Do you see the problem here? You can never prove these ideas explicitly wrong so it can be used to explain almost anything.
The tendency to interject loudly and insistently that sexism against women is the root of most social issues along with the inability to falsify those ideas is what annoys many people about feminism. When identity politics is in the forefront it causes an equal and opposite reaction.
Circling back to my previous point: I only saw feminists claiming the problem was misogyny only, never misogyny and something else. Am I willing to claim it could be the reasons I outlined and some sort of prejudice against women? Yeah, that could be the case. Everybody has a ton of prejudices. A & B & C could all be true, but I want to highlight A & B because people don't want to talk about it or don't know about it, and I think A &B are the bigger reasons. For a tsunami of talk about how women are oppressed one can casually stroll Tumblr or many corners of the internet. Hopefully after reading this blog post you've read a selection of arguments from both sides.
Obviously not all feminists are alike. If what I say doesn't apply to you, then it doesn't apply to you. I've got enough feminists tripping up even over what I didn't say to last a long time.
Ending Sentiment
Men are more in tune with the issues men face. Women are more in tune with the issues women face. This is because they live their life as a man or a woman. This means many feminists do not appreciate the problems men have, and lots of men really aren't in the business of complaining. But it also means many men do not appreciate the problems women go through well enough.
If you are a woman, traditional gender roles will have you stuck at home taking care of children. You'll be protected and people will value your lives over that of the man's, yes, but you will live a sheltered life without the freedom of being out there and doing whatever you want. You suffer a higher risk of sexual violence. If you are a man, yes, you might be seen as the head of the household. But you are expected to defend your children and woman, and think of yourself last. You suffer a greater risk of destroying your own body through stupid habits, prison, and getting killed on the job. You are expected to bring home the bacon and be a tough man in the corporate world, an empty shell there to increase the number in the checking account. Women are objectified for their looks whereas men are objectified for their utility.
But you know what would be interesting? A male to female trans woman who transitions late enough to live as a guy for a long time, but not so late as to render passing impossible. Wouldn't that give one a unique look at the world? ;)
Let's end with one of the comments in the Reddit thread, answering the core question today:
'It's culture, which is what you call it when a bunch of people have the same habits and tell each other that's how it should be. It doesn't make sense, but it is changing. Change is very slow and will continue for decades to come, but it is happening.'
No matter which side of the debate you are on, hopefully you have a similar feeling too.