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How To Get The Courage To Wear Women's Clothing In Public

Updated on June 6, 2010

This is a doozie of a leap for many men to make. It is one thing to accept yourself and have fun wearing women's clothing in the privacy of your own home, but to go out of it and expose yourself to the eyes and judgment of the world, now that is quite another thing.

I've broken this article down into sections for ease of reading. Let's start with the basic concept of wearing clothing at all, regardless of its supposed gender orientation.

Why We Wear Clothes

First of all, I would like to say that it is not actually necessary for you to go out in public wearing women's clothing at all. What we wear in public is sometimes a representation of who we are, but more often it is a representation of how we want other people to see us.

People don't spend thousands of dollars on clothing so that they feel good, they spend the money because people react differently to well dressed people. If I wander into a BMW dealership in scruffy jeans and a t-shirt with my hair kind of frizzy, I'd probably be asked to leave, or I'd at least receive far more scrutiny and less welcoming goodness than if I walked in a designer dress.

People are shallow creatures who judge on appearance. We shouldn't, but we do, therefore what most of us wear in public is either a plea to be liked and respected, or a request to be feared (think skinheads and people waving gang colors), or an appeal to attraction as in the case of ladies wearing short skirts and tube tops, etc.

If we come at the issue from this perspective, we just need to ask ourselves what message it sends when a man wears women's clothing in public. Of course, it very much depends on what he's wearing and what his intention is. A guy wearing a skirt with a business shirt and tie sends quite a different message than a guy wearing high heels, stockings, a floral dress, make up and a wig. If you live in a progressive area, you can probably get away with incorporating some elements of feminine attire into your everyday wardrobe without any eyebrows being raised. If, on the other hand, you inhabit the regions of our planet where people cling to old values that never existed, wearing women's clothing in public may confuse people to the point of anger.

The important thing to remember is that people respond not only to what you're wearing, but how you hold yourself. A man with his head held high, smiling at the world is likely to experience much more joy in his travels than a man who is scuffling about looking afraid and shifty. Remember, man is a very able predator, and if you make yourself out to be a victim, people respond to that instinctively.

The Eye Of The Beholder

Having said all that, you never know what people are really thinking. For a man leaving the house in women's clothing, he's making a personal journey, but it is a journey that changes every person who lays eyes on him. Though some people might scoff, others may very well be inspired. If the notion of changing perceptions of gender norms just by running to the store for some milk appeals to you, that may be all the courage you need.

Whatever, I'll Do What I Want!

If you have this attitude, then you already have the courage you need to step out looking fabulous in the clothing of your choice, regardless of what other people think of it. A man wearing women's clothing can be considered rebellion against the status quo, and there will be people who love you for it as much as there will be people perplexed or threatened by it.

Inspirational Statement


As I have already mentioned, you don't have to go outside wearing women's clothing if you don't want to. If you do wish to however, and you need courage to do so, think of this. One day, you will no longer have the opportunity to do so. One day all these halcyon years of mobility and existence will have passed you by. Will you come to the end of your life having lived your life in the way that pleased you, or will you have lived your life attempting to please people who don't know you or care about you? When it's put that way, it takes more courage not to go out wearing whatever you want than it does just to do it.

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