Since ChatGPT is trendy right now, I decided to ask it about going out in public as a man wearing a skirt after publishing an article about it a couple of weeks ago. I have included a couple of responses from it below which include a few good points!

When asked about building up confidence to go out in public as a man in a skirt:

Many men may feel a desire to wear skirts in public, but are afraid of being judged, ridiculed, or harassed. Wearing skirts can be a way of expressing one’s personality, style, or identity, and it does not have to be limited by gender norms. However, going out in a skirt as a man can be challenging and intimidating, especially in conservative or hostile environments. Here are some tips on how to build up the courage to go out in public in a skirt as a man.

  • Start small and gradual. You don’t have to wear a skirt for the first time in a crowded or unfamiliar place. You can begin by wearing a skirt at home, or in a safe and supportive space with people you trust. You can also try wearing a skirt under your pants or coat, and gradually expose it as you feel more comfortable. You can also choose a skirt that is more subtle or masculine, such as a kilt, a sarong, or a wrap skirt.
  • Find your motivation and inspiration. Think about why you want to wear a skirt, and what it means to you. Is it a way of expressing your creativity, your femininity, your sexuality, or your individuality? Is it a way of challenging stereotypes, norms, or expectations? Is it a way of having fun, feeling good, or being yourself? Whatever your reason is, remind yourself of it when you feel doubtful or fearful. You can also look for role models or examples of men who wear skirts, such as celebrities, artists, activists, or friends. You can learn from their experiences, styles, and attitudes.
  • Prepare yourself mentally and emotionally. Wearing a skirt in public as a man can elicit various reactions from others, ranging from positive to negative. You may receive compliments, questions, curiosity, support, or admiration. You may also encounter ignorance, confusion, hostility, harassment, or violence. You should be ready to face both scenarios with confidence and resilience. You should also have a plan for how to deal with potential problems or dangers, such as having an escape route, a backup outfit, or a friend to accompany you.
  • Be proud and confident. The most important thing is to wear your skirt with pride and confidence. Don’t let others’ opinions or judgments affect your self-esteem or happiness. Remember that you are not doing anything wrong or shameful by wearing a skirt. You are simply expressing yourself and your identity in a way that makes you feel comfortable and authentic. You are also contributing to a more diverse and inclusive society by breaking gender barriers and norms. You are not alone in your journey; there are many other men who share your passion and courage for wearing skirts.

When asked about ideas for making it easier to go out in public in a skirt:

  • Acknowledge your reasons for wanting to wear a skirt. Whether it is for comfort, expression, or fun, you have the right to dress as you please and explore your identity.
  • Find a skirt that fits you well and makes you feel good. You can shop online or in person, depending on your comfort level. You can also ask a friend or a stylist for advice on what styles and colors suit you best.
  • Start by wearing your skirt at home or in a safe space. This will help you get used to how it feels and looks on you. You can also practice walking, sitting, and moving in your skirt to avoid any wardrobe malfunctions.
  • Choose an appropriate occasion and location for your first outing. You may want to avoid places where you might face harassment or judgment, such as conservative or formal settings. Instead, opt for a casual or friendly environment, such as a park, a mall, or a café.
  • Plan your outfit ahead of time and accessorize accordingly. You can pair your skirt with a shirt, a jacket, a sweater, or anything else that matches your style and mood. You can also add some shoes, socks, jewelry, or other accessories to complete your look.
  • Invite a supportive friend or family member to join you. Having someone who accepts and encourages you can boost your confidence and make you feel less alone. You can also ask them for feedback or compliments on your outfit.
  • Be prepared for some stares or comments from strangers. Unfortunately, not everyone will be respectful or open-minded about your choice of clothing. You may encounter some curiosity, confusion, or even hostility from some people. Try not to let them ruin your day or make you feel bad about yourself.
  • Stand tall and proud of who you are and how you look. Remember that you are not doing anything wrong or shameful by wearing a skirt. You are expressing yourself and challenging gender norms in a positive way. You deserve to be happy and comfortable in your own skin.

Some of those points I also mentioned in my article, but there are a few others I hadn’t thought about which is why I thought posting ChatGPT’s response might be helpful.

See the article I wrote about the topic a couple of weeks ago here:

What do you think about ChatGPT’s opinion on the matter? 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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