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As a bit of background, I'm a rising high school senior in the Boston area. I plan on skipping college and going straight into a career of software development, most likely sticking around Boston.

The wrinkle comes around gender. I'm nb (I don't identify as a man or a woman) and I generally wear dresses and skirts, but I look like a boy. This is very obvious - although I generally shave, I still have some facial hair, and from my face and body shape it's immediately obvious to most people that I look like a guy. I'm generally addressed as a guy (for example he/his/him) and generally I don't mind too much, although I prefer being addressed to in gender neutral ways (e.g. they/them pronouns). I'm okay wearing men's clothes occasionally, but I'm distinctly not okay with wearing them all the time - if it ended up that I wasn't able to wear skirts or dresses on a regular basis at a certain job, I would certainly leave that job.

My question is when should I make this clear to potential employers? I understand that some employers might not like this, and I don't want to work at such places any more than they want me there. On one extreme, I could say nothing and then show up to the first day of work in a dress. On the other extreme, I could wear a dress to the interview. For the internship I have right now, I wore men's dress clothes to the interview, and once it was clear that he wanted me and was going to follow up with a formal offer, and then I broached the subject of dress code, and then I asked if it was okay to wear a dress or skirt to work.

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    I have to second @JoeStrazzere's recommendation to attend college. Aside from giving you the necessary technical training, college is a great way to make connections and be introduced to the sorts of companies you would want to work with. In addition, most colleges and universities have LGBT centers which would be able to offer experienced guidance for approaching a career search as a trans person.
    – David K
    Commented Jul 15, 2014 at 12:45
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    If you're working for a smaller place, dresses are often inappropriate for all genders, since even programmers have to crawl under desks occasionally.
    – thursdaysgeek
    Commented Jul 15, 2014 at 20:39
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    I have to agree with Joe and David. I've hired devs from time to time. To me I see someone with a degree I can count on them having a certain level of ability to work through policies, politics, and have a wider range of skills needed in real world programming projects. Those fresh from high school, self taught, etc. are a bit of a gamble. Some are well grounded, many have decent technical skills, but horrendous soft skills, and suffer from a "I know all" mentality. As far as transgender... guy or girl dresses are typically a no-no for programmers. Just ask if they act weird move on.
    – Eric J Fisher
    Commented Jul 16, 2014 at 19:44
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    I really don't get the "dresses are often inappropriate for all genders" comment, I've worked with plenty of programmers who have no trouble wearing dresses. I've been programming professionally for 20+ years and spend as much time under a desk as any other office worker (which is to say, little or none).
    – Binary Worrier
    Commented Jul 21, 2014 at 13:47
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    @BinaryWorrier: There are surely jobs where you need to be protected, or with dangerous machinery nearby, where a dress would be inappropriate. I knew of one job where wearing rings (including wedding rings) was absolutely forbidden (because it could easily lead to a finger being ripped off). For a software developer, I can't seriously see anything inappropriate about wearing a dress.
    – gnasher729
    Commented Apr 15, 2017 at 13:21

4 Answers 4

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You could wear a dress or a business skirt to the interview (I would go with business skirt/nice top/blazer just because it's more professional-looking than most dresses, and I personally always dress just a cut above "normal everyday" for interviews, because it's a 'first-meet/dress-to-impress' situation.) That would immediately bring the issue up, and if an employer (or more likely that interviewer) had some kind of problem with people not fitting into preconceived checkboxes, that gets brought out into the open right away. I don't think that's extreme, unless you wore a skirt or dress that was most decidedly not "interview appropriate."

On the other hand, your own solution used for getting your internship also sounds acceptable: go to the interview, get the offer, ask about the dress code and specifically about wearing dresses or skirts to work.

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    asking at the end wouldn't be bad, you'd get good practice in. Plus, it's probably best to ask this after they've established you've got your head on straight. (While I've never been in the situation, if what I perceived as a guy came in wearing a dress it'd be distracting for the actual interview process, just because I'm not used to it. Now if you nailed your interview then said, "I consider myself gender neutral, wear dresses, etc." It'd admittedly catch me off guard, but I'm a bit more progressive than most. I would have to see how it goes over with the team though.
    – Eric J Fisher
    Commented Jul 16, 2014 at 19:50
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I don't know why what I'm about to write hasn't been said yet, and I feel it's important enough to bring it up some two plus years after the original poster asked the question. For context, I'm a software developer as well, in my early 40s, and I lived in Boston for more than two decades -- it's where I made my career. In late 2013 I came out as the someone who, like you, doesn't fit traditional categories when it comes to gender (how gender was understood in the 70s & 80s had a lot to do with why it took me so long, but I digress.)

To answer your question, it is up to you to decide how to express yourself to the people around you, including to the people in your work place. At the end of the day, the people in your work place should have no say whatsoever (with some exceptions, none of which apply to software engineering) in how you dress, and they certainly have no say in how you identify. In fact, it's against the law in Massachusetts to discriminate on the basis of gender, and that law also directly refers to gender expression.

It's also inappropriate to discriminate during the hiring process. You are not obligated to disclose your gender or how you express it as a part of searching for employment.

I disagree strongly with the other answers that demand you discuss your gender with your fellow coworkers. Expecting someone who doesn't fall into traditional gender categories to "disclose" is just another example of bias -- I mean, disclose what? that you wear your clothes? Frankly, it's not your coworkers' business. If you feel it's appropriate to talk about it before you're hired, then you should definitely do that. If you don't feel it's appropriate, then don't. I have always found that employers just plain don't care.

All of this doesn't mean you won't find people who discriminate. It does sometimes feel like I have higher hurdles to jump than my fellow employees, though nobody has ever given me any grief directly. (In fact, in the few instances when gender has been brought up, it has been positive.) But, look, the people you want to work for aren't going to judge you based on your clothing; they're going to judge you on what you can do and how well you interact with your coworkers (esp. when you start moving past individual contributor roles, if you decide to go that route.) So, do your job well and reliably and stick to your guns.

You mentioned that you don't want to work for someone who discriminates any more than they want you there. (To remind: the basis for 'wanting you there' should be how well you do your job and nothing else.) I have nothing good to offer when it comes to finding the employers who won't discriminate, law or no -- it's a guessing game. But, one thing I've found is that the Northeast, at least, is open to people who don't fit traditional gender roles; this includes employers and fellow employees.

I hope you've found your place in the post-high-school world and that it's treating you well. For me, being able to live my life the way I see fit has been worth whatever little grief has come my way. (Understatement of the year, there. It's the best thing I have ever done for myself, ever.)

Make sure you know about this page, from the State of Massachusetts government: http://www.mass.gov/courts/case-legal-res/law-lib/laws-by-subj/about/transgender.html

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  • "I mean, disclose what? that you wear your clothes? Frankly, it's not your coworkers' business. " Frankly, you might consider informing any blind colleagues, the others will figure out what you are wearing :-)
    – gnasher729
    Commented Apr 15, 2017 at 13:04
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I have no idea what the laws are in your jurisdiction, nor do I care. The legal situation may allow you to hide/obfuscate your situation and then demand accommodation or special treatment when hired. IANAL, and my answer is not about the legalities of the situation, but rather my view that we should treat others the way we want to be treated.

Bring it up early, and bring it up directly.

If there is something about you relevant to the work environment, you should give them the opportunity to include it in their evaluation, and you will have the opportunity to learn from their response. It is common courtesy to provide all relevant information, and IMO deceptive to hide relevant information. Many interviews include a question like "Is there anything else I ought to know about you?" Omitting your situation is lying by omission.

If your situation is going to be the catalyst for office drama and trouble, better to find out early and avoid it.

Also -- I STRONGLY suggest that you ask for the opportunity to meet with the bulk of any team that you may be joining. You should be able to judge if your situation will be difficult or not for the group as a whole.

BTW .. I consider this advice germane for many non-standard personal situations.
I would advise the same to someone who has to care for a sick parent or child, someone in the middle of a pregnancy, adoption, or fertility treatments, someone in the midst of a nasty divorce, someone who has a hobby or vocation which takes them out of the office frequently, or someone who has a religious tenet that might impact the employer and co-workers.

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    I believe my state has protections for trans people in the workplace, but I'd have to consult a lawyer to see if they applied to me. Certainly, however, I agree that sneaking in and demanding to stay is not a good idea, even if it might be legal.
    – anon
    Commented Jul 15, 2014 at 11:17
  • Note that in the US, the mere fact that the company knows a candidate's marital status or religion (or several other protected categories of information which varies to some degree by state) can open up all sorts of "interesting" legal liabilities if the candidate is rejected. This is why good interviewers will not ask for the information, will not write it down or use it in other ways if volunteered, and might even discourage the candidate from discussing such things. This is not a straightforward problem, and transparency will not always make things easier on the company.
    – Kevin
    Commented Aug 1, 2019 at 23:13
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You should let people know the expectations early on. Even for people who are supportive, if they don't know the specifics of your expectations (e.g. pronouns to use) it makes the situation really difficult for them even if they try to go along with it. Also, in terms of etiquette and law, people might be nervous to inquire too much about it so I'd definitely be the one to bring it up rather than putting them in a situation where they feel like they have to. That being said, once you say something concise on the matter and ask if they have any questions, I'd quickly move on to something else. If you talk too much about that it might be the thing that defines you and you don't want that to overshadow the rest of your skills, experience and personality.

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