I got up a few weeks ago on Monday & started getting ready for work and decided to do my hair and makeup and wear a skirt to work. Having gone to nearly fulltime crossdressing in my personal life, I have been gradually transitioning to presenting as a woman at the office: my hair is in a very cute and girly blonde bob, and I've been wearing makeup some days and my nails are polished most of the time. I've been wearing a lot of women's tops with cardigans plus ankle pants or leggings or capris, with flats. (There have been zero responses from co-workers, other than a couple of double-takes.) But I hadn't planned to make the full transition on that day, I just kind of woke up and said "I'm going to do it."
Well, I ended up changing out of the skirt , but I did curl my hair and wear makeup, and I decided to call HR and have the conversation about transitioning. I work for a very large and very progressive global corporation and I knew slightly our HR rep. I was confident she would be helpful and professional.
I emailed her and she replied quickly and we ended up talking the next day. This conversation was confidential.
I explained my situation, letting her know that I was already wearing mostly women's clothes to the office, and I was thinking of moving to skirts and dresses. She was very kind and gracious and asked some really good questions ("What sorts of responses have you experienced in your personal life, dressing as a woman?" and "How would you like your colleagues to respond? What would be the ideal reaction, for you?")
And, as I expected, she basically said "How can we support you through this transition?"
We talked for a half-hour or so and she said "I will come up with a plan and get back to you." The plan consisted of speaking to my 2 immediate supervisors, plus the person who runs the small office where I work, plus our overall department head, just to let them know what was going to happen and where to go if they had questions. I came out of that conversation thinking "Yes! I'm ready to do this!"
She sent me an email a few days later reviewing our conversation and laying out the plan. I took a couple of days to think about it, and I ended up deciding to hold off, for now.
Partly this is because I am pretty happy with where I am, in terms of gender ID at the workplace. I've been shopping for some more business-casual women's wear and have found some really cute outfits that are clearly feminine without being dresses.
And partly this is because the world has gone crazy since then. This was actually before the pandemic really struck, but oil prices had plummeted (we do energy research and analysis) and I am a manager of a small team, and we need all hands on deck. It didn't feel like the right time to raise my hand and say "I'm going to start wearing dresses to work!", if you see what I mean.
Still, I'm very glad I had the conversation, & got the information, and I feel really good that 6 or 12 months down the line, if I decide to make that move, the option is there.
Thanks for reading!