The First Time I Wore a Skirt in Front of My Parents

As most of you know, I openly wear skirts in front of everyone which is something that has gotten easier over the years since I started. At first, however, I hid my passion only doing it when I was alone at home which I know a lot of men do, especially at the beginning.

I like to document the personal hurdles I have faced on my journey here on this blog as I hope it will help other men who are still uncertain about wearing clothes typically found in the women’s department in front of other people.

That said, this is the story of the first time I wore a skirt and heeled boots in front of my parents and how they reacted.

On Camera

A few years ago, I visibly wore a skirt and heeled boots on a video call with my parents for the first time. Since we live on two different continents, video calls are our primary form of communication. It wasn’t the first time I had worn them on a call with my family, but as a lot of us know from working remotely, you can’t normally see what someone is wearing below the waist on camera.

At some point, I got tired of hiding it from my parents and decided to just show them rather than tell them about it. In order to do that, my wife and I called them from our living room with a camera mounted on top of our TV while we were sitting on the couch. That meant, my parents got a clear view of me sitting there with my skirt and boots.

We chatted for a while and no one brought it up. Frankly, I don’t think they even noticed. At a good point during the conversation, I decided just to show them. I stood up and presented the skirt I was wearing, then I lifted one of my legs and showed them the heeled boots I had on. You can see pictures of the black a-line skirt and the brown heeled boots below.

At first, there was stunned silence but it didn’t take terribly long before my mom asked why. I proceeded to explain my views on clothing being genderless, the comfort of skirts, etc. I could see their somewhat confused, blank expressions though, so I didn’t go too deep into the subject.

Fortunately, my parents are pretty accepting even if they don’t understand it. My dad didn’t say a whole lot, but my mom asked questions. She wanted to know if I go out that way, what my wife thinks about it, how long I had been doing it, etc. My wife and I answered her questions honestly and happily. Afterwards, we moved on to other topics and it wasn’t a big deal.

A Panicked Phone Call

Well, it wasn’t a big deal until I got a somewhat panicked call from my mom the next evening. She said she had been thinking about me wearing the skirt and heels and one question kept crossing her mind over and over again: Is this the first step of him telling me he’s transgender?

She was a little panicked because she is, unfortunately, not open at all to the idea of gender and biological sex not being one and the same.

I assured her I wasn’t, even though I was in a phase where I was at least questioning my gender a little bit. She calmed down and told me she was fine with me wearing “women’s clothing” as long as I “still stay a man”. You might interpret that phrasing as implying that she actually does believe gender is changeable contrary to what she says she believes, but that is beyond the scope of this story.

In any case, she stayed true to her word and it has not been a big deal since then. She even borrowed one of my skirts for a baptism earlier this year.

Wearing a Skirt in Front of Them in Person

The first time my parents saw me wearing a skirt in person was when my wife and I traveled to the US to celebrate Christmas with them later that year. I didn’t wear a skirt while traveling because I wanted pockets while traveling and all the skirts I had with pockets at that point were pencil skirts that didn’t have enough range of motion to be comfortable for long, international travel.

As such, it wasn’t until the next day that they saw me wear my first skirt in person. The skirt I chose for the occasion is a tartan-patterned woolen skirt that is very much kilt-like in appearance. It has the added benefit that it is incredibly warm and since my parents live at a high altitude, winters tend to be very cold. I wore black, cotton leggings with it like in the picture below.

This time, my dad did comment. He said he really liked the skirt and that it looked warm and cozy. Since he hadn’t said anything about the topic up to the point, it made me very happy to hear a compliment from him. My mom also commented on it, saying that she also liked it.

I wore more skirts while I was there, including the same black a-line skirt I wore on camera for them the first time. My mom’s comment on it in person was that it looked better on me than she had thought. It was apparently difficult for her to see the outfit properly on camera.

Generally, seeing me wearing skirts in person let her see that they didn’t look strange on me like she had feared. Since she had never seen a man in a skirt, she was worried that it would somehow look strange, but was oddly surprised that I still looked the same… just in a skirt.

Conclusion

While it seems silly now that I would have such trepidations wearing skirts and heels in front of my parents, it was serious business at the time. I am extremely happy I made the step though because it was not only a confidence booster but also a huge relief. It was extremely liberating. I have a good relationship with my parents and I hate hiding things from them that are important to me.

I understand that not everyone has such understanding parents though. My parents are generally open to new things, but also often skeptical. It takes them a while to accept some things and I think me wearing gender-non-conforming clothes was one of those. I’m just grateful they didn’t make a big deal out of it and have learned to be comfortable around me wearing what I want to wear.

Here are a few pictures of the skirts and boots I mentioned above: