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This feels like it works best for middle and upper middle class trans/gender non-conforming (GNC) people, and terribly for every other kind of GNC person.
Whether it is technically legal or not, a male-bodied teenager who comes into a job interview with lipstick and a dress is likely not going to get the job. Good numbers are hard to get, but there's plenty of anecdotal accounts from trans people who had trouble finding work because they were non-passing trans people, and I don't think there's any strong reason to doubt their accounts even without good hard data on discrimination that shows up in "legible" parts of society.
I seriously doubt affirmative action, and DEI initiatives have made things much better for all trans/GNC people in this regard. (I mean, isn't it common knowledge that the biggest beneficiaries of affirmative action have always been cis white women?) Sure, a progressive tech firm might happily hire a trans woman as a software engineer, but for every company like that there's probably a dozen bodegas and fast food joints in more conservative areas that don't want to hire a teenage cross-dresser in their first job, and that lack of work experience might echo out into their job prospects down the line, amplifying the effects always present because of their status as a recognizable cross-dresser.
Part of the reason that Weimar transvestite passes looked interesting to me, is that they seemed like exactly the sort of legal vehicle that one could attach non-discrimination laws and cultural norms around. I know more libertrian or social conservative types would still have issues with such a regime, but I do think it would overcome the basic issue of "telling a societal lie" that many people claim is their main objection, and I think a world with transvestite passes and social norms of pronoun hospitality (enforced by social censure, and not legal censure) could get 90% of where trans advocates want things, and without any obvious "lies" or "metaphysical nonsense."
I think it's going to be a lot easier to move the needle towards "okay, boys can wear dresses too" the way we moved it on "okay, girls can wear trousers too" than inflicting on society that we must believe "in fact biology not real, you can be a girl or a boy or a girlboy or a no-gender if you just feeeeel it".
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This doesn’t seem to me like that much of an imposition. “I really like wearing dresses, putting on makeup, and doing up my hair.” Okay, great, do that on your own time, not at work, and especially not at a job interview. I really like dressing casually, not caring what my hair looks like, and only shaving every couple of days, but I wouldn’t dream of going to an interview wearing blue jeans and sporting two days of stubble, and if I did, I definitely wouldn’t expect to get the job.
There’s this idea floating around that you need to be your “authentic self” 100% of the time, and everyone around you needs to accommodate that, which is absolute nonsense. Anyone who’s ever had a non-PC thought or who’s ever enjoyed a dirty joke knows he can’t get away with expressing either one at most work places, and everyone accepts that that’s right and proper. Or, going back to clothing, take that episode of The Office where Jim showed up in a tuxedo. The writers of that episode relied on the audience knowing that a tuxedo is inappropriate attire in an office setting. But if Jim had instead come in dressed like Marilyn Monroe, somehow that’s supposed to be fine. No. Wear a tux, wear a dress, or tell an inappropriate joke on your own time.
(And while I’m grousing about clothing, Zoomers need to stop wearing pajamas and athletic wear in public. Sweat pants are fine for lounging about the house, but there’s no reason you should be wearing them at work or out in public. Show some self-respect.)
At the moment it's inappropriate because that's not tolerated gender role behaviour. Great, if gender is socially constructed, let's change the roles. I hate makeup and wear as little as possible. If Johnny there loves it and religiously watches contouring tutorials on Youtube, let him doll himself up for work and let me just cover the worst of the red blotchy skin with a dusting of powder, and neither of us have to claim that "in fact I am a girl/in truth I am a boy" to be permitted to do this.
If after all that Johnny is still "no, I really am a girl", okay, let's examine that. But if Billy just wants to wear heels to work, that doesn't mean he's not a boy, then live and let live. I think it would be a lot less stressful on everyone, and we'd have the advantage that the narcissistic exhibitionists couldn't use the figleaf of "I am being oppressed" so we'd all know the ones who are trouble.
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Depending on the job, I'm going to go ahead and take the conservative position that, yes, this is inappropriate at an interview and should not be protected, along with very visible tattoos and facial piercings. There are still employers who think that it's cool anyway, just maybe not as mainstream. Especially the lipstick, if it's showy. This is partly aesthetics -- most men are not going to be able to pull it off with visual dignity. I don't have a problem with Billy Porter's tuxedo ballgown, because it looks cool. But, yeah, if it's a basically normal service job, and they come in looking like this, then they are absolutely signaling, not so much femininity, as high maintenance and potential social and legal trouble. In my experience, women who dress up and apply showy makeup significantly more than their female co-workers, especially if they are older and/or already married, also tend to be Bad News.
This is distinct from non-work contexts. People should have all kinds of freedom to wear lots of quirky things in general.
The transvestite pass seems either useless (nobody is currently arrested for cross-dressing), or oppressive towards everyone else ("pronoun hospitality" sounds like an outside force telling people what pronouns to use without the trans person having to do anything particular to win them over).
While this is technically true, I don't assign 0 credence to the reports from some underclass trans black women that they get stopped by the police on suspicion of prostitution more often than the average person. While the so called "walking while trans law" law (properly the "loitering for prostitution" law) I'm most aware of in New York was repealed in 2021 after years of efforts going back to at least 2010, it wouldn't surprise me if there are several other jurisdictions where anti-prostitution laws accidentally catch innocent trans people in their nets.
I think part of the problem is that underclass trans women probably are more likely to be prostitutes, and a police officer is going to Notice The Pattern whether he wants to or not, and then he's going to act on his experiences and stop non-passing trans people more often as a result.
I fully admit that this issue could be solved with reforms to prostitution laws, without any reforms of existing legislation around trans people (including transvestite passes), but that doesn't mean it's not a problem for underclass trans women right now.
Than the average person, sure. Than the average woman dressed similarly... I'd have to see evidence on that one.
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I am absolutely willing to believe that things are really tough for this group in multiple ways, along all the intersectional axes.
I'm most familiar with South side Chicago, and was under the impression that current policing practices for underclass blacks were to try to do as little as possible within their own neighborhoods, but I suppose they would get unwanted law enforcement attention elsewhere in the city. I got some unwelcome cop attention for trying to visit a little beach next to a wealthy suburb, and I don't belong to any Concerning Groups. But I'm also slightly concerned that American police are currently being reformed into doing nothing at all, and if an innocent black trans woman is beat up by their local gang, I would probably like it to be investigated -- it seems like a very hard problem.
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