AI-generated Man in a Skirt in a City

Since I’ve started wearing skirts, I’ve come up with a number of ways to build confidence in wearing them and other gender-non-conforming clothes out in public. One of the ideas I had a while ago, was to plan a multi-day trip to another city but with a twist: I would only bring skirts.

This is an idea I’ve entertained for a while now. Essentially, the plan is to take my family on vacation for several days to another city and leave all my bifurcated lower body garments at home. I’m going to travel there in a skirt, regardless of whether by car or train, and then once I’m there, I won’t have a choice but to wear skirts out in public unless I want to hide in my hotel room for the entire trip.

While I thoroughly enjoy wearing skirts out in public and do so on a regular basis, it still costs me a lot of energy to get over that initial hesitation before leaving the safe space of my home. That means, I usually have less energy for whatever I am going out to do simply because of this nonsensical hurdle in my own head.

The hope is that going to another city for several days with only skirts will force me to practice getting over this hesitation so that it doesn’t cost me any energy at all anymore. Once I’m out, I don’t have a problem anymore and enjoy the experience. The best way to get over a fear is to face it and this would force me to face it much more frequently and thoroughly than when I am at home and don’t have to leave the house every day.

The other factor that plays into it is anonymity. At home, I’m not really worried about my neighbors and what they think because they’ve all seen me wearing skirts already anyway, but there is still comfort in the total anonymity you get when you are in another city where no one knows you. The likelihood of you seeing someone twice in a large city that you don’t frequent is very small.

In any case though, I decided to write about my idea so that it might help others. Maybe some of you who are struggling to find the confidence to go out in public in gender-non-conforming clothing will find it helpful. If you do, definitely let me know how it went! I would love to hear about it!

As far as my own plans go, I will write another post about it here once I’ve done it. We don’t have any concrete vacation plans yet, but I’m sure we will later in the year. I will write about how it went and what my experiences were. Hopefully, I’ll even have some photos to share. I’m optimistic about it and am even looking forward to 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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