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?