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The "wholesome" in Wholesome Crossdresser means, approximately, "not a Creepy Crossdresser".
No idea whether it still applies to Jesse James under this definition; don't remember much about this particular historical figure.
Trouble Cube continues to be a general-purpose forum for those who desire such a thing.
Wholesome Crossdresser means the crossdressing is considered wholesome, as opposed to the older portrayal in which crossdressers are portrayed as sexual deviants, or worse (like silence of the lambs).
Also, I wouldn't use Wholesome Crossdresser for Jesse James. He did pose as a woman, but mostly as subterfuge in furtherance of committing criminal activities (as in disguising himself so he get closer to his targets).
Edited by laserviking42 I didn't choose the troping life, the troping life chose me
The whole concept of a Wholesome Crossdresser is somewhat transphobic today, perhaps not so much for the wholesomeness, but for the implication that most crossdressers aren't wholesome. It still appears in works of fiction, of course, but here we're describing a real-life person, so using the trope here has unfortunate implications.
Secondly, I agree that it's very doubtful whether there was anything wholesome about disguising yourself as a woman in order to commit crimes.
And thirdly, I agree with the OP that it creates an odd dissonance to use the word "wholesome" in a sentence that describes a person as a criminal and slave-owner.
My suggestion: axe the link to Wholesome Crossdresser, both because of the dissonance and that the trope doesn't apply.
How does the line about crossdressing even fit the rest of the example. Him being pro-Confederate and stealing medicine is relevant because it contradicts his romantic image. But does crossdressing? I think the whole sentence should be cut.
I think this part of a recurring issue where people forget that tropes' names have specific meanings. The person who wrote this was probably just so used to using Wholesome Crossdresser to mean just "crossdresser" that the issue never occured to them.
Edited by TheMountainKing
I remember reading this example a while ago and thought it had a pothole calling him a Creepy Crossdresser.
Just change it to Crossdresser. I personally think Wholesome Crossdresser is too broad when it allows anything not explicitly against crossdressing but that's something else to discuss. Also the italicizing in the example is kind of obnoxious.
vvv Ohhh, that makes sense.
Edited by mightymewtron I do some cleanup and then I enjoy shows you probably think are cringe.
Yeah, I'd just change it to a plain Crossdresser link; opinions about crossdressing aside, it definitely isn't something that's part of the pop-culture view of him.
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Judging from laserviking's comment
the appropriate trope would actually be Disguised in Drag.
@mightymewtron I added the italics in the OP to emphasize the points of issue. They arne't in the actual example (so far)
I changed the link to Crossdresser now.
I found this example on Jesse James and well... (italics mine)
I'm pretty sure "Wholesome" and "Confederatenote /slaver" are mutually exclusive terms. So I question the link to Wholesome Crossdresser in that example. Thoughts?
Edited by MorningStar1337