I know I am late to this post, but let me just begin with the following image:
http://1.bp.blogspot.com/-czW31bSnRAM/T ... kimono.jpg
The garment to the left is pink, made of silk, worn by a man, and most importantly, is made for a man.
I don't think very many people would think that the gentleman in that picture is trying to pass as a woman.
The Hanfu is my favorite go-to garment for challenging the idea that a man can't wear beautiful clothing with elements considered feminine by western society's arbitrary standards.
I am with Moonshadow, and others, who have chimed in: you should wear what you enjoy, and what you think looks good on you. If you look in the mirror, and are happy with what you see, how you feel, and are prepared for the consequences of wearing it in public, then go for it!
Just recently, I started wearing dresses in public. The first dress I chose to do this is this:
https://www.dressbarn.com/plus-size-sea ... mendations
I chose it, because I think it looks good on me, if I wear a black cardigan with it. (I have a mustache, and beard, by the way, so I don't think anyone could accuse me of trying to pass as a woman, either.)
Believe me, it took courage to do so, and many exasperating days of chickening out, after almost wearing it to work. But, when I was able to, I felt better than ever, and I also feel my sense of fashion has improved from it.
As others have mentioned, there aren't any fashion rules for us to follow. We are the trailblazers. (With the exception, perhaps, of color matching...I still can't get the hang of that beyond matching neutrals with 1 color/pattern)
If you want to wear a skirt that has no so-called feminine traits, then have at it. If you want to go out dressed in flowers, frills, and jewelry, but aren't ready for any negative consequences, then, nobody will blame you for keeping your skirts "manly," or shame you as a "coward." However, if you think a floral dress with a gathered, knee length skirt flatters your body, and your only obstacle is your self-assessment of being a "sissy," don't let that stop you. Don't let society's arbitrary gender roles tell you who you are. You know
who you are, and it is so much bigger than the box society tries to stuff you into.