Thursday, September 1, 2011

Boys in Dresses: A Primer

The title of this is a bit misleading, as I'm mostly going to talk about guys in skirts. However, I like the sound of "Boys in Dresses" better, so go with it.

One of the interesting things about being a guy in a skirt is that there are nearly as many opinions about how to wear skirts as there are men wearing them. For classification purposes, I like to think of it as a spectrum. On one end of the spectrum we have the "Bravehearts", men who only wear kilts. On the complete opposite end of that spectrum, we have the androgynous boys, who prefer to blur the lines between gender. These two ends are very different, and to be honest I often see them clash in the internet community. Let's break it down, shall we?

So we will start with the aforementioned Bravehearts, men that tend to stick exclusively with the kilt and its various accessories. I'm aware that the kilt is a traditionally masculine garment, so if anything this is right at the edge of the spectrum, but only because I oft see people call a kilt a skirt regardless of historical or cultural connotations. Personally, I do view kilts as a type of skirt, albiet an accepted men's skirt. My wife tells me that a kilt is only a kilt if you don't wear anything under it, otherwise it's a skirt. As a result of this, I apparently don't own any kilts. Anyhow, the Bravehearts keep it strictly masculine, and don't delve into any women's fashions.

Next on the spectrum are men who do venture a bit further down the skirted path, and begin to incorporate skirts designed and marketed to women. To be fair, this group takes up a large part of the spectrum. Closest to the Bravehearts are the men who will wear skirts from the women's department, but only if they are "masculine" enough. From what I've seen, this mostly seems to involve denim skirts or muted colors in a-line cuts. These guys usually keep the rest of their wardrobe strictly masculine. There are some varying philosophies on this, and I'd like to take a moment to digress a bit and discuss them now.

From what I've gathered from reading posts from men who do this, the guiding philosophy behind this style of dress seems to be baby steps, for lack of a better term. The idea is that the social stigma against men in skirts will only change over time by careful and deliberate small changes. Once a man in only a skirt is accepted, then we can work on other garments or more feminine styles, but for now we need to keep a low profile and not push the envelope too far. I don't agree with this view at all, and I'll explain why later in this post.

There is also a rule that I see floating about called the "One Item Rule." Essentially, the idea is that you only incorporate one item of feminine clothing into your wardrobe at a time. The idea here is quite similar to the one above, to not impose too much "deviancy" (for lack of a better word) upon the viewer at once. So if you are going to wear tights, you had better wear some men's shorts and tennis shoes with them! Sorry, but my thoughts on this? Boring!

Back on topic, sliding a bit further down the spectrum you start to see men incorporate more than one garment at a time into their wardrobe. He might wear a skirt with tights, but still keep the rest of the outfit very masculine. I've seen this look work great, though I think it can be a bit difficult to find that perfect balance. While it isn't really my style, I do respect the few men I've seen pull this off.

As we approach androgyny we must first come into the area I fall into, men who ignore the gender label on clothing. This man will wear skirts, dresses, tights, heels, whatever, but will still keep his appearance male. He believes that clothing has no inherit gender, and that it's silly to put such restrictions on fabric. Speaking personally, to me it's about men having a full range of expression and experiences.

Lastly, we come into the androgynous look. This boy blurs the line between male and female. I often see supporters of androgynous fashion write about a world where gender doesn't really matter, where someone isn't strictly viewed as a boy or girl so much as just a person. In that world, gender doesn't put any limits or expectations on you. While I don't go for an andro look personally, that's something I can really get behind anyways.

I said earlier that I would post my thoughts on why I push as far as I do in this post, but I feel it's already gotten too long. If you've made it this far, thank you. My opinions on why I do what I do will have to be another post, so stay tuned for that!

So that's a broad view of the spectrum as I see it. If you feel I've missed something, I apologize and please feel free to tell me about it in the comments section. In any case I would love to read your thoughts on this topic. Where are you in this spectrum, or where (if at all) do you feel it's gone too far for you?


  1. Brilliant commentary, my friend! If I were to categorize myself, I'd say that I'd fall into the same one as you, that I'm simply a guy who likes wearing women's clothes and shoes, nothing more complicated than that. I don't at all consider myself being a crossdresser, at the end of the day, I don't want to LOOK like a woman, I just want to DRESS like one. I find your commentary to be very thought provoking and look forward to reading more.

    1. Going back in time a bit to say ...

      Thank you, JeffB! Sorry I missed replying to this!

  2. yes yes yes i agree but courage... how? is it possible to live today with a few dress that do not just hide in our closets? I really dislike the gender category and strongly wish a department store did not have a right and left side but just a clothing store. I greatly admire your courage and ideals. thanks so much for sharing.

    1. Unfortunately, there's really no magic formula for courage here. I write this blog and post my photos to try to provide some inspiration and courage to others, but I know that every situation is different. Everything you see and read here is an open part of my life that I share with everyone around me. The looks you see are what I wear daily. I know it isn't always easy to be different, though. I have a lot of support, particularly from my lovely wife, Mrs. Spookshow. My hope is that my presence here can show that it is possible to be yourself and live the life you want.

      Thank you for taking the time to comment here, Wilkid!

  3. Hello :)

    I've just discovered your blog via and noticed this bit:

    "He believes that clothing has no inherent gender, and that it's silly to put such restrictions on fabric."

    Ah yes indeed. Even though I'm from the cross-dressing/trans* side of things, so the gendering of clothing has always been quite important to me, lately I've been taking this "non-gendered fabric" viewpoint more and more. In fact I've just blogged something similar myself:

    1. Glad you found the blog, Jonathan. I gotta say, I checked out your blog and I love it! I always find it really fascinating to read about sartorial experiences from different perspectives than my own. Thanks for chiming in here!

  4. just found your lovely blog :) i like-y what i see!

  5. Love your blog and your skirts,dresses,etc. We need more of this to encourage more of us men who love wearing skirts and dresses and nylons etc., to be able to wear what we like when and where ever we like with out fear of ridicule or harassment. Thank you, and keep it up and some day,hope fully soon, I'll have the nerve to go out dressed in my skirts, or what ever else I might like!

  6. What you're doing is awesome and I really look up to you for doing it. I'm starting to figure out my androgyny, though, and am wondering if you have any suggestions for blogs by and/or about androgynous boys to follow. Thanks for any suggestions!

  7. Hi Michael

    Just found this site. Sat here typing in red heals, a denim mini over opaque soft tights and a loose black low cut top. I have a couple days beard growth and all is cool.

    Just want to say, liking your blog and sense of ease. You've got a good look going and kudos to Mrs Spookshow. Good luck with the baby and keep going along your own path.