The prevailing wisdom in the transgender activist community is that only transitioning transsexuals have workplace issues. According to this reasoning, a transgenderist should feel safe that, should their status become known, they will not be fired or otherwise discriminated against at work. Crossdressing, goes the theory, is an off-duty activity. Only transsexuals have rights at work.
But is this really true? Isn't it our policy for each employee to be as productive as possible? Can we really function at our peak if we hide who we are? In the words of Carly Fiorina, at the time a Vice President of Lucent Technologies, (currently CEO of HP) "Lucent values your contributions when you bring your whole self to work."
What if you are off duty and crossdressed, but you are paged to come into work to handle an emergency? Must you do a quick change before you can enter company property? What if you have a hair styling appointment, or artificial nails, and you can only schedule the appointment during lunchtime? Must you telecommute that day?
At the same time, it is important not to lower workplace productivity or morale by creating a disruption in the workplace, or by imposing a burden on your coworkers. Our employees are used to women wearing pants at work, but they are not yet used to changes of gender. A compromise is necessary to best meet everyone's needs.
This section is written with male-to-female transgenderists in mind. Females who dress and act in a masculine way are protected by the "gender expression" rule but are still considered women. These guidelines would also apply to a female-to-male transgenderists (or butch) who presents as a man (e.g. to "pass.") If this applies to you, please reverse the pronouns and accept my apologies for the m2f language.
If you are crossdressed some evening in town, and a coworker happens to see you and recognize you, you can relax. This discovery will not cause you to be fired, harassed, or suffer on the job. If the employee is unaware of the Safe Space policy, and you do not wish to be outed at work, you should request that your coworker keep your "secret." Outing you at work, disregarding your stated wishes, could be considered harassment and a violation of the EO policy.
If you choose to come out at work, you can do so without fear. Coming out is best done in a personal face-to-face meeting, either one-on-one or with a group. Allow time to explain who you are and answer questions. Being "out" does not necessarily mean you crossdress at work. But it permits you to honestly explain if you pierce your ears, shave your legs, or the like. Appointments for events such as hair styling need not be restricted to non-work hours and can be explained honestly.
There are several situations when crossdressing at work may be appropriate. They are listed here in increasing order of controversy.
So what to do? Be cautious, conservative, and considerate of others. If you decide to crossdress at work, get the advance consent of those you work with. The support of your boss will be vital. If you cannot convince your boss that crossdressing is appropriate for you, you should reconsider crossdressing, or negotiate a compromise with your boss.
If you have a bona fide need to crossdress at work, either because of a personal mental health need or a business need, or you can document that it will improve your productivity, your crossdressing is appropriate. If you cannot get support from your boss, work with your ERG or HR for support or to help reach a compromise.
If the crossdressing is for your personal convenience or your improved peace of mind, you must negotiate in advance with your primary coworkers. In many cases, coworkers who have attended a diversity workshop about transgender issues will not object. However, if one person objects strongly enough to complain, or if more than one person is uncomfortable (which can affect their own productivity) the crossdressing is inadvisable.
If your job requires contact with customers, crossdressing at work may be inadvisable. Certainly we cannot dictate the preferences of customers. If crossdressing were to cost us a sale, or generate a complaint, the company would be forced to act. In jobs where a dress code applies, such as sales, you should think long and hard before crossdressing on a day you have face-to-face contact with a customer.
Recognize that, even if people accept you and are courteous to you, they will still gossip. Transgenderism is new and sensational. The first African American employees were no doubt controversial, as were the first women and the first openly gay employees. By crossdressing at work, you are identifying yourself as part of a new and poorly understood minority. Expect snickers and stares, especially from those you see in the hallway that you don't work directly with.
Some people you meet will burst into laughter, even if they are trying to be supportive. I suggest you look upon this as an opportunity to bring joy and mirth into others lives, turning it into a positive event.
In some people's eyes, you may lose some respect. A few coworkers may be totally unable to deal with it, and may reduce their interactions with you to the minimum required by their job.
If you follow the transgender community customs, you should be addressed by your femme name when presenting as a woman, and your male name when presenting as a man, with the appropriate pronouns (She/her or He/him/his) to match the presentation. However, it is important that you not impose a burden on your coworkers. Answer to both names. If your coworkers are supportive, it's OK to gently correct them if they get the pronoun or name wrong, if they are trying to get it right. But if they insist on calling you by your male name, accept it and answer to it.
I tell people I work with that my name is Mark, and my nickname is Mary Ann, and it's OK to call me either. I continue that, if they want to be especially supportive, it's nice if they call me by the name that matches my current gender presentation, if they can tell. (By phone and e-mail, it's difficult to tell.)
A related issue is what to call you when you are not visibly there. If you attend a meeting as a woman and are assigned action items, those should be recorded in your primary (male) name, as you will likely be presenting as a man when you carry them out. Your documented name for job roles, referrals, team memberships, and the like should be your primary name. On the phone or by e-mail, use your primary name unless the other person knows you are transgendered and are currently crossdressed, and even then, use the femme name only if they agree.
If you intend to crossdress full time, always presenting in the opposite role at work, then your primary name and pronouns will match your new gender role. In this situation, the guidelines for transsexuals apply to you. It is not necessary to have surgery or HRT, only to transition permanently into a new gender role at the workplace.