Getting Ready to Go Out in My Heeled Boots

This post is going to be a little different than most of the other posts I have written because it is going to be about wearing heels rather than skirts. While I wear skirts more often than heels, I do enjoy the occasional jaunt in higher shoes. 

I started wearing heels before skirts. In fact, they were the gateway drug that led me down the road to other typically “feminine” clothing. Most of the time, I wear them with skirts, but sometimes I pair them with jeans as well. In fact, I originally worked up the courage to go out in public in heels and jeans before I did in a skirt.

Out in Public in Heels

Since I started wearing heels, I have been out in public in them numerous times. My favorite type is boots with a block heel that isn’t ridiculously high. Not only do I really like the way they look on me, but they also have the added benefit of looking a little more “masculine” and therefore more inconspicuous. While that isn’t the reason for them being my favorite, it did initially help me build up the courage to go out in them for the first time.

At first, I wore them out a few different times in the city of Munich, Germany. I ran errands, went to dinner with my wife and generally just wandered around the city doing what I would normally be doing in flat shoes. Just like my first time out in public in a skirt, nobody paid any attention. Other people are just too busy doing their own things to care about what kind of shoes you are wearing.

Once I was confident enough in them, I decided it was time to take it to the next level and wear them to the office.

At the Office in Heels

The first time I wore my heeled boots to work was before COVID hit and I was commuting every day. I wore them every day for almost two weeks before someone finally commented on them. One of the managers looked at my shoes and said in a friendly tone that “only an American can wear shoes like that”. I’m an American living in Germany, but to this day, I’m still not entirely sure what he meant by that.

The second experience came a couple of years later which was probably due to COVID and all of us having to work from home. By then, the worst of COVID was over and we were back at the office for a Christmas party. Of course, I wore a pair of heeled boots and towards the end of the evening, once plenty of alcohol had been consumed, another one of the managers pointed at my feet and said that he found it ironic that one of the tallest employees wears heels.

I am 6’2” (188 cm) flat-footed, so he wasn’t wrong about me being one of the tallest in the small company. We were standing around in a small group of people talking and of course all of them looked down to my shoes. It actually made me happy that he pointed it out because it gave me an opportunity to talk about it which is something I love to do.

I replied telling them I love wearing heeled boots because I think they look good and I feel comfortable in them. They were all actually very interested in the topic and even asked questions. One of the women who wears a lot of heels asked what size shoe I wear and when I told her (13 US, 46 EU), she asked where I buy them. She explained that she has bought a lot of heels, but had never seen them that big.

I won’t go into each and every question that was asked because I honestly don’t remember most of them. What I do remember, however, is the feeling of elation I had after that conversation. Not only did I get a lot of incredible, positive feedback from the others, but I also thoroughly enjoyed talking about it and answering questions. My colleagues were very intrigued and honestly interested, which is the experience that I have had from most people with both heels and skirts.

My Heeled Boots in the Office
Me in Heeled Boots at the New Office

Starting a New Job in Heels

Since that experience, I have changed jobs and it had absolutely nothing to do with my choice of footwear or clothing. By the time I started my new job, I was wearing my heeled boots (of which I have several different pairs) more often than not when going out in public in cooler weather. Experience has made it normal for me and I don’t even think about it anymore.

As such, I decided to wear a pair of them on the first day of my new job. Although I work entirely remotely now, I have to travel to another city to go to the office every once in a while. I was required to be at the office for the first couple of days and it was there that I wore my heeled boots.

The first day was, as always, a whirlwind of activity, meeting people, getting access to all sorts of things, being shown some of what I need to do, etc. I didn’t have the capacity to even think about what was on my feet and no one else said anything either.

The second day, however, there was a comment. One of the women who also works there told me she had seen me in the boots the day before and that she absolutely loved them. She wanted to know all about them: where I got them, what brand they are, why I wear heeled boots, what my experiences have been as a man in heels, if I wear other types of heels, how often I wear them, etc. It turns out she is a massive fan of the same type of boots that I was wearing and was thrilled to see a man wearing them too.

Of course, I answered her questions honestly and ended up telling her about all of my (still) unusual wardrobe choices, including that I wear skirts most of the time as well. She got more excited than I’d ever seen anyone get about the topic of a man wearing typically “feminine” clothing outside of the community of men who do just that.

Since then, we have had several conversations about it and I even sent her the links for this blog as well as my Instagram account. She forwarded both of them to her husband who she is apparently now trying to convince to branch out into more feminine styles of clothing.


While this post diverged a little bit from the topic of skirts, the main point of it was to show that wearing unconventional footwear or clothing in public and semi-public settings is generally not as scary as you think at first.

In my experience of regularly wearing heels out in public for the past few years, not a single negative thing has ever happened. Either people ignore you entirely, don’t notice your choice of footwear or engage with the topic in a constructive way. Every single person who has mentioned my shoes has been genuinely curious and supportive.

It’s still unusual to see a man in heels or a skirt which is why people ask about it. Having to explain it time and time again might get tedious sometimes, but it does help them understand and accept it. The more this happens, the more normal it will become and the less stigmatized it will be which is why I am patient and even happy when people ask me about it.

Do you wear heels? Have you spent any time out in public in them? How about other “feminine” clothing such as skirts? What were your experiences? Have you had to explain your choices to a lot of other people? Let us know in the comments below!

Image Gallery

  • Heeled Boots at the Munich Airport
  • Heeled Boots at the Munich Airport
  • Heeled Boots at the Drug Store
  • Getting Ready to Go Out in My Heeled Boots
  • Getting Ready to Go Out in My Heeled Boots
  • Heeled Boots at the Frauenkirche in Munich, Germany
  • My Heeled Boots in the Office
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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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