Building Up the Courage to Go Out in Public

Wearing a skirt, dress, high heels or other garments generally considered by Western society to be women’s clothing as a man in public takes a certain amount of confidence, rebellious attitude and independence. For a lot of men, it is unimaginable even if they enjoy wearing such clothing at home and would love to be able to wear it outside.

Building up the courage to wear them in public can be distilled into a single basic point: confidence. You need to be confident and comfortable wearing them to pull it off. That takes practice, but it also helps if you are prepared for reactions from other members of the public.


The first few times out of the house tend to be difficult because most of us have a deep-seated need for other people’s approval and are afraid of negative reactions. Going against the grain doesn’t generally garnish that approval we crave. 

That being said, once you’re out of the house, any nervousness eventually subsides as you realize that nothing is going to happen to you. At first, you will feel like hiding in the dark shadows so that no one can see you, but the reality is that most people won’t actually pay any attention. 

Of the few people who happen to notice, most won’t care enough to say or do anything. They may do a double-take or raise their eyebrows, but they would do the same if you were wearing a clown suit: they do it because they are surprised by seeing something unusual.

If someone does say something, however, it will generally be positive. In my experience, I have had women compliment my outfit and my courage to wear heels or a skirt outside. So far, every compliment I have received has been from a woman. I don’t think that men necessarily think more negatively about it, but rather that they have been conditioned to believe that complimenting another man’s outfit is “gay” or some other nonsense — just think back to how boys treated each other in elementary school. They wouldn’t even do it if you were wearing a sharp, hypermasculine, custom-tailored suit.

Unfortunately, there will still be the occasional bad actor who feels like he or she has to tell you how (not) to dress. That person may hurl insults at you or ask you if you are trying to be a woman, but that is either a form of insecurity on their part or a rough way of trying to understand what they are seeing.

In order to deal with a negative reaction, it is important to understand where that person is coming from and why they are reacting negatively. In my experience, they fall into two categories: they are insecure or entirely confused.

A lot of men are insecure in their masculinity despite giving the impression that they are superbly confident. Those are the types that will be insulted by you appearing confidently in “feminine” clothes and they may feel it necessary to say something in order to patch up the hole you just punched in their fake masculinity. That is especially true if they are with a group of friends and feel the need to prove themselves.

The sight of a man in non-gender-conforming clothes will be entirely strange to a lot of people. If they ask stupid questions, such as if you are trying to be a woman, that is just their way of trying to understand what they are seeing. You might consider it a temporary malfunction of the politer part of their brain while they process what their eyes are presenting to them. Some may mean it maliciously, but they fall into the first category of being insecure. Most who ask dumb questions will just simply be too stunned to realize they are doing it. In that case, a patient, confident explanation will go a long way.

Confidence Is Key

As the header says, confidence is key to being able to pull off wearing anything unusual in public and making it look good. That applies just as much to dresses as it does to clown suits. There are plenty of people out there lacking the confidence to wear a clown suit in public.

Knowing why you enjoy wearing such clothing will help you feel more confident. Not only will it allow you to understand yourself and eliminate any insecurities you might have about what you are doing, it will also give you a ready explanation for people when one inevitably comes along who asks the dreaded why.

Practice is also key. At first, you should wear the clothes around the house and get a feeling for them. You should be used to your own appearance in them and have experimented with what looks good on you before you go out in public. It is, after all, a change in style.

If you have been doing that for a while already and are just ready to make the jump into the public sphere, then I suggest working up to it by wearing hybrid outfits. Start with something masculine like a kilt. You may still get the occasional sideways glance from other people, but it won’t be because you are wearing clothes typically associated with women!

From there, move to skirts combined with a masculine shirt before wearing full dresses out. Slowly but surely introduce more and larger elements from your more feminine wardrobe rather than just go all out the first time.

If you are trying to work up the courage to go out in high heels, then start low and more “masculine”. Don’t go straight for the 6” stiletto sandals that we all love. Instead, go for low, block heels. Many of them even have a softer heel that is silent so that they won’t attract attention like the clicking of normal heels would. Chelsea boots or any sort of short boot is a good choice to begin with because they aren’t as obviously feminine. As with skirts and dresses, gradually work your way up to your most feminine pair of heels.

You should incorporate all of these into outfits you’re happy with. If you can look at yourself in the mirror and be pleased with what you are wearing, it will be a huge confidence booster! That will take a bit of experimentation, but you will eventually find combinations that suit you.

Another way to boost your confidence is to talk to like-minded people. There are numerous forums and get-togethers of men who enjoy wearing gender non-conforming clothing and many of them are veterans of wearing it in public. There is nothing quite like group support and reading or hearing about other people’s experiences for encouragement!


When I began writing this article, I certainly didn’t intend to include as many references to clown suits as I did, but the more I thought about it, the more I realized that wearing one in public isn’t a whole lot different than wearing a skirt or heels as a man: it takes a healthy dose of confidence and will surprise people.

Of course I don’t mean to say that skirts or dresses are in any other way comparable to clown suits. For me, it is about what it requires of a person to go out in public in one. But then again, clown suits are very colorful and boisterous and as such will attract a lot more attention than a well-thought-through outfit that includes, say, a skirt. So I’ll let you be the judge as to which one would be more difficult to do.

In the end, it comes down to being confident by preparing for other people’s reactions, understanding your motivation, practicing and being happy with your outfit. The more you brave the public sphere and engage with the community of like-minded men, both online and locally, the easier it will get. At some point, you’ll even wonder why you were hesitant to do it in the first place.

Have you gone out in public in a skirt, dress, heels or some other typically feminine article of clothing? What were your experiences? How did you build up the courage to do so? Let me know in the comments below!

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About the Author

In many ways, Alex is a typical man who just so happens to enjoy wearing skirts and high heels. He is married to a wonderful, supportive wife and has a young son. His hobbies include reading, programming, metal music, playing instruments, video games, cars, hiking and a number of other smaller things.

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