When The Man Becomes The Other Woman
It is surely no secret by now that many women aren't exactly on board with the men in their lives wearing women's clothing. We can point out at great length how much of a double standard this is (I wonder how many women have been wearing jeans whilst they complained that the man in their lives wanted to wear a skirt or lingerie) but the type of woman who is put off by a man who wears women's clothing doesn't care about logic of that nature.
You see, women, like men, like to be right. And women, like men, like to have what they consider to be their needs met. Some women believe that they need an entirely masculine counterpart in order to be happy in their relationships. (In much the same way, some men consider a woman unattractive if she doesn't wear a skirt and high heels and make up, so let us not pretend that double standards and silly expectations don't exist on both sides of the fence.) When a man wears what is considered to be feminine clothing, it can change a woman's opinion of him. It would be nice if it were not so, but it is. Women are visual creatures too, and for some women, the sight of a man wearing feminine things is quite simply, a turn off.
Why? Well, there are many reasons. The most obvious one being the fact that straight women like to be the source of all femininity in a relationship. If a man embraces his feminine side, a woman can find that threatening. Should she? Of course not. Will the fact that she shouldn't find it threatening mean that she doesn't? Of course not. Women feel how they feel. However, a woman who loves her man for reasons other than the fact he is a male figure that handily slots into her life and provides manly attention has a greater chance of getting over the fact that he likes feminine things.
You see, men are people too. Women often complain about being objectified, but they spend a fair amount of time objectifying men right back, even to the point where if a man doesn't dress 'right' (and often that has nothing to do with wanting to wear women's clothing, its more likely to do with the fact that he has a favorite shirt that he won't stop wearing, or he insists on wearing trainers everywhere) she will often attempt to 'change' him. We've accepted, to some extent, the woman's right to determine what her man looks like, as if she were his mother. It's bizzare and wrong and it doesn't go back the other way, but there you have it.
The only real advice I can give to men who don't want to deal with illogical and, one might say, bigoted objections to their choice of dress is not to involve yourself with women who feel that way. If wearing feminine things is part of who you are, find a woman who respects that. Plenty of them exist. Being with a woman who turns up her nose and makes snide remarks when you wear what you want to wear is like being a man of color who decides to marry a racist woman, it doesn't make any sense. People who really love you don't care what you wear. People who want you just to fit their 'fairytale wedding, happily ever after, two kids and white picket fence' fantasy aren't in love with you, they're in love with a stereotype, and if you settle for that, then you are opening yourself up to a world of hurt. It makes no sense to spend your life being persecuted by the one person who is supposed to love you no matter what because of the clothing you wear. The fact that men marry and stay with women who clearly don't embrace who they are and who shame them into wearing clothing they don't like is beyond me, but it happens, and that too, is a choice that men are free to make.
In an ideal world, people would find partners that complimented them and made them feel good. In reality, people settle and compromise all the time, often over things that they should not settle and compromise over. People choose, quite knowingly, lifetimes of nigh misery where they feel alienated in their relationships. Why they do that we may never know, perhaps it is because they do not know that there are women out there who will accept them, perhaps it is because they simply fall in love with these pretty bigots and decide that they can change, perhaps it is because the harping voice of an unsatisfied wife reflects the inner judgment they have that they shouldn't be wearing women's clothing. The reason is no doubt different for every man.
Many men who love women's things live in a gilded cage, the door of which is always open. If they choose to mate and stay with partners who bring them down in fundamental ways, then that, unfortunately, must be on their heads. We cannot change the world, we can only change ourselves.