Transitioning at Work

During March 2014 I went full time. Like most transitioning men and women I had transitioned everywhere but work. Work was the scariest place to transition since a disaster there would be hard to recover from. Work would also place the greatest demands to date to be dressed and present appropriately, and determining what appropriate means is difficult when you’ve only been presenting for a year.

Your work environment is distinct from mine. Don’t use my experience as a guide to be followed. Judge based on your work environment.

My approach was to set reasonable expectations and to rely on the kindness of strangers – OK, coworkers. I hoped that they would afford me some wiggle room and to their credit they did.


“Be prepared” If you’re a transwoman like me, you should already have been living as a woman well before you’re going full time. You should have been getting hair removed from your face, and know how to cover up what’s left if need be. More importantly you should have a realistic view of what you should be wearing.

Observe women your age. Sure, all us  middle aged people are disappointed that we aren’t twenty. You have to get past that or you won’t pass well in public and you’ll be inappropriate at work. You should have been doing this for going out in public, it is much easier to get by in public spaces if you aren’t dressed in a way that draws attention and nothing draws more attention than an inappropriately dressed mature woman.

So no mini skirts, excessively deep necklines, and don’t even think about going into the stores meant for 20 somethings to shop (or the junior section even if you can fit the clothing).

Even with this you’ll see that the women around you pick styles that work for them. You need to do the same. If you have narrow hips you should forget skirts that tightly hug your bottom and show that unfeminine feature out.

I personally disposed of the breast forms as soon as I started transitioning. Visible breasts help a little in having a good presentation, but it isn’t the single factor. Plenty of cis women are flat chested. Personally I felt that being genuine with whatever little I had was more important for me.

Go easy on the makeup. Foundation to even out your skin or not if your skin is good. A little subtle blush can make things nice. Mascara is good for daily wear. Forget bright eyeshadows and excessively loud lip colors until you know what you’re doing and what works for you, and remember that the office isn’t a nightclub. And practice, practice, practice.

Buy a modest amount of office wear clothing. Depending on different factors you might gain 15-20 pounds from hormone therapy. Personally I bought too much, and while I have a forlorn hope to fit into the pretty size 14 skirts again, my honest assessment is that it’s going to be a while (or maybe never).

In all this, clothing, makeup, presentation, take advantage of the resources at your disposal. Talk to women you’re close with for advice, and remember that if someone comments in a negative way they’ve overcome a societal norm to do so – take it seriously.

The beginning

When I actually went full time I started with feminine clothing that was close to what I wore before. That was my approach. I started with slacks, nice shoes but not excessively feminine, an appropriate top and a sweater or blazer. I wore earring but otherwise went modestly with jewelry.

After a few weeks I started adding skirts and then dresses, and allowed myself some leeway about makeup and shoes. Did all this make a difference – hard to say, things went well and might have gone well anyway.

Try to not second guess how people will react. Those you think will be the greatest challenges may well prove to be your best supporters. I had just a couple of uncomfortable men in my department. To their great credit they did not make this my problem.

Expect gossip and do your best to ignore negative messages going around. Before my first day as Rachel in the office I heard there were opinions about my character going about. Your behavior in the office and your personal life will be the most powerful rebuttal.


You have to expect that everything will not be perfect going full time. Expectations are your greatest enemy on this journey. There is an enormous temptation to live in a fictional future day when transition is over and we are living a perfect life. If this is your approach you may well find yourself a little regretful because the reality is never ever going to meet your fantasy world.

At work there are many issues that can come up. I’ve been fortunate to not have issues over my authority or technical expertise, but you might. This is a commonly reported issue for many.

There may be a vocal or non-verbal fuss over the ladies’ room. It took three to four months for it to not be an issue. Not a word was ever said to me, the ladies just voted with their feet until they realized it isn’t an issue.

Resist the temptation to read meaning into unfriendly looks. The person may have had a bad day, or they might be a misogynist. It may have nothing to do with reading you.

Smile and keep smiling, it is a great antidote to sour looks. There’s something deep inside that makes us smile back, us it to your advantage.

You may well have some trouble with coworkers. If  possible talk with your management and get their support and help in dealing with this. Remember that this is not your problem, you haven’t done anything wrong.

Last, gender dysphoria is a singular problem however important. Don’t expect that living as your true self will fix all your problems. It may be a huge step and extremely helpful, but expect to work at your happiness.



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