"I would never want to be a woman. That would spoil all the fun of dressing like one." - Carly*
I don't know if anyone noticed, but I put up the definitions of the words I use (and feel free to mention if I need to add any more or you have problems with the ones I put up). I wanted to elaborate a bit more on why I define transgender as I do. Which is:
An adjective describing a person whose gender (part or all of it) does not match the sex they were assigned at birth. Transgender makes no assumptions about the person’s genitalia, sex, gender role, presentation in daily life, or anything else- only the disconnect between what the doctors assumed the person would be and what the person actually is.
Now, I know that's not how everyone uses it- particularly as an umbrella term. One thing that there tends to be some disagreement on is whether or not people who don't uphold gender norms (crossdressers, drag royalty†, etc) are included in this. And here's my take on it.
Some crossdressers and drag royalty are bigendered or genderfluid (or actually trans [wo/wer]men but haven't accepted that yet) or something along those lines- the "desire" they have to crossdress is the same as a werman or woman "desiring" to dress like a werman or woman, respectively. To me, that isn't really crossdressing. A bigendered maab who wears dresses to express her womanhood isn't "crossdressing" any more than a woman wearing a dress is- she's expressing her female gender by wearing clothes associated with females. The fact that she isn't always a woman or is also a werman doesn't devalue her female gender in any way. And even if this person is crossdressing, aka dresses like a woman when he's a werman even though he's a woman at other times, they still fit into trans because their gender both does and doesn't match their assigned sex- not because of the clothes. (of course, in the literal transgender sense of "across-gender", they might be the only ones who really are transgender, as they actually go across genders)
So what about the wermen, the people with only one gender and whose gender matches their assigned sex, who want to wear a dress? (or women who... whatever counts as crossdressing for women, I'm not really sure)
I don't think clothing has a gender. Now, yes, socially genders are assigned to clothing. But the bounds of what's considered "acceptable" for wermen and women are ill-defined and change with time. Are wermen who wear "skinny jeans" crossdressing? Are women who wear loose jeans? They aren't even consistent over all of US culture- subcultures, age groups, races, classes, and geographic locations can all have different limits of what is and isn't "acceptable" clothing for wermen and women, much less all countries. Is a werman who wears a kilt crossdressing? What about if he's wearing an unbifurcated garment designed for wermen? Now, people can obviously crossdress in the same sense as crossplaying- dressing up with the intention of dressing as a different gender, but I don't think it makes you trans any more than playing a character who's another gender makes you trans.
A person can't express gender they don't have- I can't express my female gender by wearing a skirt because I don't have a female gender. Even if a werman (and, yes, this applies to women- but generally you hear about maab crossdressers and drag queens) is intentionally dressing to look like a woman, he isn't expressing his gender as a woman- his gender is still that of a werman. And, seriously, no one bring up the bi/multi-gender thing, I just spent a paragraph explaining that.
Similarly- I don't include otherwise cis people who have non-standard presentation/traits for the same reason. I don't think a werman who likes shoes is less of a werman than one who likes football (or that a person can't like both), and a woman who prefers playing rugby to getting her nails done isn't less of a woman either (and rugby players can enjoy getting pampered as much as anyone).
I also don't like the concept of clothes having a gender because people use it as a basis for discrimination. If a person is perceived as crossdressing, even if they're wearing clothing quite appropriate to their gender (just not assigned sex) or don't feel what they're doing is crossdressing, they can face a lot of problems for it. Last year a man was threatened with arrest for wearing a skirt in a courthouse (a skirt that would have been appropriate on a woman, based on the description). If that's what applying genders to inanimate objects gets us- I don't see any benefit in it.
For the time being; crossdressing, gender variant, and other people who have a gender that matches their assigned sex but don't entirely fit the gender roles/traits/expectations of that gender might functionally fit in (at least with 'queer') in the sense that they can face trans- & homophobia for it, but I really don't like the idea that someone is somehow "less" their gender just because of the clothes they wear or the things they enjoy. And, of course, trans does not mean "less"- but why would we call a person who is otherwise cisgender "trans" just because of the clothes they like to wear? A person being trans implies that their gender is different than what cissexist society expects people with the genitalia zie had at birth to be, and that zie'll have a harder time being accepted as that gender because of that. A maab werman has a gender that very much matches what society expects, people will rarely have a difficult time believing he really is a werman- even if he expresses that gender by painting his nails pink, strapping on 6" heels, and putting on a lovely dress.
It also causes confusion when it comes to trans people who have non-standard presentation or who enjoy crossdressing/playing, drag, etc. If a cis werman is transgender just because he likes to wear dresses (even if he does full-time)- what is a trans werman? Trans people already face far more pressure to fit their gender's roles/traits/expectations than a cis person is ever likely to face, saying that your presentation somehow effects your gender only adds to that.
*The quote is from "Too Much Information", a webcomic featuring a transvestite- Carly (born "Carl Lee"). It comes from this page, but I'll give a warning that I'm not sure if it's misgendering or not. It either says that he thinks Carly is a trans man, or that he thinks trans women are really men, Carly's reply implies the latter- and also mislabels the fact that trans women are women and says that they just "want" to be a woman, implying they're actually men or at least not "really" women. That 1-page slip aside, the comic is pretty cool- though adult and NSFW. I put it as a footnote to explain this, though.
†Drag Ace is a joke, but I like it. Basically my line of thought was "What would you call a neutrois in drag?", as most titles are gendered, and going over the face cards in a deck (one thought was "joker")- since 'ace' is slang term for an asexual, I liked it. Drag Royalty is because there aren't really non-gendered terms for queen/king, but both are royal titles. I think that one's more self-explanatory than ace.