What AI Has to Say About Wearing a Skirt and Heels as a Man

I have been playing around with Microsoft Bing’s new AI feature and just out of curiosity, I thought I would ask it a couple of questions about wearing skirts and heels as a man.

First, I entered “How to wear a skirt in public as a man” to see what it would come up with:

Wearing a skirt in public as a man can be a rewarding and liberating experience, but it can also be challenging and intimidating. Here are some tips on how to wear a skirt in public as a man with confidence and style.

  • Choose a skirt that suits your body type, personality, and occasion. You can opt for a tennis skirt, a pleated skirt, a mini skirt, or any other style that you like. Make sure the skirt fits you well and is comfortable to wear.
  • Pair your skirt with appropriate tops, shoes, and accessories. You can wear a shirt, a blouse, a sweater, or any other top that matches your skirt. You can also add a jacket, a scarf, or a hat for extra flair. For shoes, you can wear sneakers, boots, sandals, or heels, depending on your preference and comfort level. You can also accessorize with jewelry, belts, bags, or sunglasses.
  • Be confident and friendly. The most important thing is to feel good about yourself and your outfit. Don’t worry about what other people think or say. Most people won’t even notice, and the rest won’t care. The only person who thinks it’s a big deal will be you. Smile, walk with your head held high, and enjoy your skirt.
  • Be prepared for some reactions. While wearing a skirt in public as a man is not illegal or wrong, it is still uncommon and different. Some people may stare, comment, compliment, or criticize you. Some may even be hostile or rude. Don’t let them get to you or ruin your mood. Ignore them, respond politely, or walk away. Remember that you are not doing anything wrong or harmful by wearing a skirt.

Wearing a skirt in public as a man can be a fun and empowering way to express yourself and challenge gender norms. Follow these tips and you will be able to rock your skirt with ease and grace.

As you can see, it actually came up with some very good advice! I was surprised by the results.

Next, I entered “How to wear high heels in public as a man” and this is the result:

If you are a man who wants to wear high heels in public, you may face some challenges and judgments from others. However, you can also enjoy the benefits of heels, such as looking taller, more confident, and more fashionable. Here are some tips on how to wear high heels in public as a man:

  • Choose your heels wisely. Depending on your style and comfort level, you can opt for elevator shoes, low-heeled boots, wedges, or stilettos. Elevator shoes and low-heeled boots are more subtle and easier to walk in, while wedges and stilettos are more noticeable and require more practice. You can also look for heels that match your outfit and occasion, such as dress shoes, casual shoes, or boots.
  • Know your size and fit. If you are buying women’s heels, you need to know your size conversion and fit. Generally, men’s shoe sizes are about two sizes larger than women’s shoe sizes. For example, if you wear a men’s size 10, you may need a women’s size 12. However, this may vary depending on the brand and style of the shoe. You also need to consider the width and shape of your feet, as women’s shoes tend to be narrower and more curved than men’s shoes. You may need to look for wide or extra-wide options, or try on different styles until you find one that fits comfortably.
  • Learn how to walk in heels. Walking in heels is not easy, especially if you are not used to it. You need to practice at home before going out in public, and start with lower or thicker heels before moving on to higher or thinner ones. Some tips for walking in heels are: relax and stand up straight, keep your feet parallel and point them forward, take small and slow steps, land on your heel first and then roll onto your toe, and avoid walking on uneven or slippery surfaces.
  • Be confident and unbothered. Wearing heels in public as a man may attract some attention or comments from others, but you should not let that affect your confidence or enjoyment. Remember that you are wearing heels for yourself, not for anyone else. You have the right to express yourself and your style however you want. If someone gives you a compliment, smile and say thank you. If someone gives you a rude remark or stare, ignore them or speak up for yourself politely. Don’t let anyone make you feel ashamed or insecure about your choice of footwear.

Again, the results are impressive!

It seems that the trend of men wearing skirts and heels has become popular enough that even AI is picking up on it and is able to give advice for those who are still unsure about it.

What do you think of AI? Do you think it’s something that could be used to further our cause? 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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