Why do I feel like it is wrong?

[Shyheels]

I think a lot of this is conditioning - we’re, as in society at large, are not conditions to seeing men in heels and so when we do see it, it looks strange, unsettling. And we don’t like being unsettled. That very much colours our perceptions which are already burdened by the forbidden aspect of wearing heels.

I looked at myself in a full length mirror while wearing by stiletto boots, and if I looked objectively - setting aside all the issues associated with being a guy in heels, but just stuck to aesthetics - I couldn’t see a problem. I happen to be tall and with slender legs thanks to a lot of cycling, and if you were to take a photo of me from the waist down, in skinny jeans and in stiletto boots,  I would not raise an eyebrow. The assumption would be that this was a photo of a woman’s legs in stiletto boots. It’s only when we see that, no, it’s actually a guy that our censoriousness kicks in and says this shouldn’t be.

It’s the unease we don’t like, not the visuals

[WedgesAreFun]

1 hour ago, Shyheels said:

I think a lot of this is conditioning - we’re, as in society at large, are not conditions to seeing men in heels and so when we do see it, it looks strange, unsettling. And we don’t like being unsettled. That very much colours our perceptions which are already burdened by the forbidden aspect of wearing heels.

I looked at myself in a full length mirror while wearing by stiletto boots, and if I looked objectively - setting aside all the issues associated with being a guy in heels, but just stuck to aesthetics - I couldn’t see a problem. I happen to be tall and with slender legs thanks to a lot of cycling, and if you were to take a photo of me from the waist down, in skinny jeans and in stiletto boots,  I would not raise an eyebrow. The assumption would be that this was a photo of a woman’s legs in stiletto boots. It’s only when we see that, no, it’s actually a guy that our censoriousness kicks in and says this shouldn’t be.

It’s the unease we don’t like, not the visuals

I hear this a lot being pushed in the new mainstream and it all seems rather forced and coerced. The mainstream now (media, colleges / universities etc) that this is all just a "social construct", but the reality is people are afraid to object publicly for fear of repercussions against them, they might lose their job, they might in some countries that don't have a first amendment protection get arrested (see how authoritarian the UK, Australia and New Zealand and some other parts of Europe are becoming).

The reality is that it isn't conditioning or cultural norms, if you look at ancient men wearing dresses and skirts you will see how different it is from men wearing womens clothes today. In ancient cultures where men wore such things it was made for them, it was cut for them, fabrics and materials for them, it was functional first and made for the male form, it wasn't trying to present an hourglass figure or be embellished with frills (except some strange period in Europe where mens shirts had lace trims which was short lived, but even still they were added to clothes cut for men) or really bold garish colours.

Womens clothes are designed to accentuate the qualities in women we like, such as the hour glass figure, the frills and lace exude a delicateness which pairs with the feminine ideal of lightness etc, but a man should not be delicate or light if he is to be attractive to women.

Clothing does exude certain properties that embody either the masculine or the feminine and when you mismatch it is visually apparent. Historical mens clothing that came in the form of dresses, skirts and such were made in a way to exude the properties of masculinity inline with the innovations of their time, mainly plain, bulky and kind of boxy in shape, and in no way trying to display an hourglass figure etc.

Same with heels, heels were originally invented for men for riding horseback to keep your feet in the stirrups, they were purely functional in nature. Over time some (definitely not all) men wore heels who were from upper class to signify that they are above the rest of society and their feet don't touch the mud but those men were generally regarded poorly by the rest of society, I cannot substantiate that but I do believe from what I read a while back they were a minority even amongst the upper class.

The thing is, they just don't make heels or dresses / skirts for men anymore (except for kilts) because they are not designed in a masculine way with the male figure in mind or are embelished in feminine ways. Getting society to make such things and go back to that way of doing things would be very difficult, you would have to basically dress in existing cultural attire to do this, such as the dresses worn by men in African or middle eastern countries or go back to dressing like a medieval age monk.

But if you take clothing and shoes designed for the female attributes, embelished with feminine attributes and wear it as a man it will always appear as contradictory to the norm in any society in any period of time throughout history.

[Shyheels]

I’m talking about wearing boots, heels. We all wear something on our feet. A hiking boot is a hiking boot, a trainer is a trainer, pretty much no matter which side of the shop you’re buying from. It’s just when you tinker with this one particular design element common to nearly all forms of footwear that all the angst starts. High heels are seen as feminine so virtually no men wear them. When you do see a man in heels it looks odd, unusual, confusing and since we tend to like to have our expectations met, it seems unsettling. What I am saying is that it is more likely to be this unsettled feeling that makes us question and doubt how we look in heels rather than any objective aesthetic.

[mlroseplant]

Ah, the age old discussion of what is masculine and what is feminine. There is some room for discussion about that. I do not think anything I wear looks particularly "girly," but others would violently disagree with that self-assessment, the most important of these being my wife. Body type definitely plays into the whole thing. I don't think I look very feminine, but I am small, so finding so-called "men's" clothing and shoes has been a bit of a problem all of my life. What I wear on a daily basis would probably look ridiculous if I were 6'3" and 220 lbs.