Over the years I bought a light up Xmas shirt, fuzzy house socks, a pull over blanket shirt, bathrobe, all because I liked them. They all could have been unisex in many ways. I don't go looking but I certainly do not avoid. Just forgot as a kid I loved long night shirts for cold days I would pull my knees up and tuck my feet inside.
I totally agree with the sense of comfort that you are describing. During periods of cold weather, I find it constraining to always be confined inside pants and cinched up with a belt around my waist. I prefer to wear long tee-shirt dresses or long button-down robes. If they have pockets and feel comfortable, I have everything I need to feel both sensual and practical at the same time.
Dresses are the perfect winter attire when the weather gets too cool to be nude. My dresses do not look frilly, because that does not appeal to me as a man, but the comfort factor is huge. Men, take a hint from our sisters, dresses feel great!
Well, yeah, if the temperature is below 45 degrees. But long dresses can be made of heavier material and keep your core warm. I have dresses that keep me warm when working in the garden or around the house. Lots of good pockets and stretchy enough to move your legs freely. I have house dresses that I can sleep in when the house interior is cool. And now, I have become so used to not wearing a belt that I just use suspenders when I must wear pants under certain circumstances. Belts feel like an annoying tourniquet on me. They cut my body in half and take away that sense of flow between my brain/heart and the rest of my body.
If it's simply asking that men cross dress, I don't think that will happen any time soon. However, I know many men, myself included that are not adverse to breaking cultural stigmas for clothing. I have a Scottish heritage in my family and would regular go in full regalia to clan meets. Aye, there's naught but what god granted me under ma kilt. I am also a bit of a japan-o-phile and enjoy wearing Yukata. I have 2 different patterns and Haori to go over them.
I pull my cock and balls up in front of my cycling shorts. If I don't after 5 miles my cock is numb and balls are sore the next day. They are very visible through the spandex in front but I remain decent, not that I really care, by pulling my jersey down in front. Now when I wear my trisuit there's no hiding anything.
Once when my girlfriend and I were on a daytrip to the nearby receational area in the mountains, she slipped on a stepping stone while crossing a litle creek and got soaked. She started shivvering in the cold air so we returned to my car where I had spare clothes that I used for my construction work. She dried off and dressed completely in "men's" clothes for the rest of the day. No one gave her a second look. There is no longer ANY concept of "crossdressing" applicable to women. As a radical hippie, i want that for men, just like when it became acceptable for men to have long hair.
Women in modern society don't worry about their body contours being revealed in their clothing choices, so why should men? Liberation!
While I’m not looking to wear women’s clothing, I have admired the thaws of the Middle East. They look delightfully comfy.
A lot of it is a fear of being perceived as being gay not just by men but by women. It takes some real courage for a guy to were clothes viewed as for women in public and not intend it as a joke. I thought part of masculinity was being brave maybe more people should practice a little more courage.
Men will be able to liberate themselves (and their wardrobe) when society let's them. And that's NEVER.
A humanities professor once told me, according to all of their evidence, the problem is people are just too stupid. So, I tell people to "Get Over It Already!" According to the experts themselves, the problem is the same people they teach are too stupid! Explaining why Donald Duck is emperor of the world, we've made the stupid dictionary taboo, and a quarter of the population still claims the sun revolves around the earth. Thankfully, classic logic is rapidly becoming obsolete, ensuring the Three Stooges will soon learn the hard way, Mother Nature's Love Is Irresistible, But She Has A Wicked Sense Of Humor!
You assume that there is some unseen, unnamed stigma that is holding people back. Did you consider the fact that it may be a matter of simple comfort? Conformity works both ways...if you insist on someone breaking societal conformity for something else, you are just trying to enforce a different conformity on them. I am most comfortable in jeans and a T-Shirt for daily wear. If I were to go to a corporate job interview or meeting I wold wear appropriate attire, regardless of my preference, because that is the norm in that environment. When I attend Cultural festivals (The Highland Games) I dress in my Family's traditional Kilt and Scottish Regalia. But I don't run around everyday in a Kilt, not because i am ashamed of it, but because it is impractical. Asking why Men don't Cross-Dress is like Asking why people like Coke over Pepsi ... Answer: It's a choice. As much as the world has changed, I still believe in free will and freedom to choose.