Feeling Trapped in a Skirt

Wearing skirts as a man can be incredibly liberating. The extra freedom of movement you have (at least if you’re not wearing a pencil skirt), the cool breeze on a hot day, the wide range of patterns, cuts and styles: it all translates to more freedom and choice.

But have you ever felt trapped while wearing a skirt? It is a feeling that I have unfortunately had several times throughout my skirt-and-heel-wearing journey. Since Western society is not used to men wearing these types of clothing, it means that I often feel like I am trapped inside the house if I am wearing such a garment.

If I want to go out, then I have to build up my courage and my strength to do so. It is a massive effort on my part to mentally fortify myself to face the outside world and other people’s expectations of me despite knowing that I shouldn’t pay any attention to them. When I do muster the strength to do so, it is incredibly liberating and exhilarating and I am extremely glad to have done it afterwards.

However, I am not always able to muster that strength. If I feel like wearing a skirt or heels, but am tired or having a stressful day, then sometimes I simply feel trapped at home. I feel like I can’t go outside or even open the door if the doorbell rings. I can’t go anywhere or do anything outside of the house as though I am putting myself under house arrest.

As much as I love wearing gender non-conforming clothing, that is really a problem I have with it. It certainly isn’t the skirt’s or the heeled boot’s fault, it’s society’s inability to accept men, or anyone really, wearing unusual clothing. Even the “rebellious” goths and the punks have a certain look that is expected of them.

The result is that I often wear gender-conforming clothes at home when I am tired or stressed even though I would prefer to wear a skirt. It bothers me immensely, but it costs strength to defy society’s expectations of you, even if you’re only doing it in your own head at home.

Have you ever felt trapped in a skirt, dress or high heels? What are your experiences with it?

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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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