When a woman (or female) leans towards the masculine side of appearance, it is empowering. It is pushing the boundaries. Women can wear pants, and even suits, and they are perceived as strong and independent. Women can take traditionally masculine jobs, such as construction and trades, and they are perceived as equalizers. They are branded as pioneers, because the progression towards masculinity is acceptable.

When a man (or male) leans towards the feminine side of appearance, they are shunned. They are considered weak, broken, and disturbed. Men can not wear skirts or dresses without being perceived as homosexual, as psychologically damaged and without being shunned by society at large. When men take traditionally feminine careers, such as nurses and interior designers, they are almost always the subject of humiliating jokes, and perceived as homosexual. The whole of society shuns them; even a majority of the LGBT community seems to be uncomfortable with males who either crossdress, or are transgendered. A woman in pants is a beacon; a man in a dress is (at best) the butt of a joke.

Why is that? Well, the best conclusion I can make is that there is an inherent flaw in our culture that men are superior to women. The characteristics of being masculine are considered positives: strength, power, bravery, intellect... But, women have desirable traits too. The problem is that our society perceives feminine traits as those such as 'weakness, frailty, soft, gentle', when in fact, women have many desirable traits, which can vary depending on your perspective of women and the role they have played in your life...

I imagine that many guys who cross the proverbial line into femininity are seeking to gain traits such as 'sexy, seductive, powerful, elegant.'; and there is nothing wrong with wanting to be any of those things. Yet, while the fade from female to masculinity can be blurred without consequence, the line from male to femininity can not. In many countries, it is considered a crime. In many places in the world, walking on the street as a guy in womens' clothing is an immediate death sentence, by the hands of unskilled, self-made executioners with blunt objects. In other places, you are more likely to get taunted, laughed at, and harassed... While a woman in pants is very widely accepted, a man in a dress is still a stigma, or a cheap joke in a situation comedy show.

If you think about it, it doesn't make sense. If females can be masculine (F=M) than shouldn't males be able to be feminine? (M=F) Mathematically, the principle is sound, but in society it is not. I think that's wrong. They are just clothes. It's just makeup. The simple fact is, it shouldn't matter- and in reality, it doesn't- but we still think it matters, and so the stigmas are perpetuated. We are slow to let go of the things we think we know.