What should I do when people are uncomfortable seeing me in a dress?

Miri
5 min readAug 1, 2024

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I used to just ignore it. I was making a point [gender freedom] in a take it or leave it fashion. Today, I am more sympathetic. I have come to see that gender is the most important social status we have. And, importantly, I am obviously not following the ordinary rule book for gender.

I am male, and I have been wanting to wear dresses and other feminine clothing since age 5. It feels perfectly ordinary and satisfying to me. Unfortunately, my first show and tell to my parents went badly. I learned in no uncertain terms that for a male child, this impulse was not only not permitted, it was wrong, shameful, and needed to be instantly stopped.

Why? I wondered. Seemed natural to me. I couldn’t and still can’t, 70 years later, find a meaningful objection to males wearing dresses, or females doing whatever they want to do in ‘boy territory’.

It was a very fundamental urge for me, so I just did it in secret- a lot. In fact, nearly every time I had a private moment. Dressing up was a huge psychic magnet — lowering myself into a deep well in which my true self was somewhere to be found.

However, living a double life is deeply problematic. I was doing the best I could as a boy child to meet man standards, but running to my hidden stash of girl‘s’ clothes whenever I was alone, as a way of trying to hang on to my girlness. It wasn’t just dresses I liked- I also wanted to have more room to express a social femininity- in how I stood, sat, and moved. And, yes, how I thought and felt, listened, and shared my own feelings. As the years went on I would try to surface myself, but over and over I found my trying to have some social femininity was not something others could accept.

The upside of this was that I was functioning successfully in economic terms as a man in society, and securing a family livelihood. The downside was that it was a huge drain on me. I censored all my communications and expressions, and this disassociation from my genuine feelings negatively impacted all my relationships.

Gender status defines our place, confers powers and privileges, and lays down obligations and restrictions. Everything we do with other people in society is prescribed in some way by gender status. The way we dress, the way we hold our bodies, the way we use our eyes in conversation, the things we know we can ask for…. Every last detail of living.

Viscerally, the first thing we all want to know about a figure approaching is whether man or woman. For eons, the approach of a male or female determined two massively important things- reproductive or just sexual opportunity ,and basic safety.

No wonder so many people feel confusion, and then that something is unsettled, wrong, and out of bounds when they see me in a dress. My appearance is one of mixed signals. Bodily, I look like a typical manly man- strong, tall, bearded, and … I am wearing a dress and shoes and jewelry that ordinarily would be on a female woman and signal her place in the matrix of females. I am not lumbering, but I am not delicate. I am forthright, and friendly, not hesitant or ashamed. I clearly don’t feel out of place, yet I am not female. What should they do? What is it I want?

It was always a little tense going out in a dress.

Finally, when I fully accepted the simple validity of what I felt, I found peace. I relaxed and let my womanliness surface, and my world changed.

In that peace I understand that my sense of feminine gender is internal, and my certainty about it is secure. It is a feature of my personality. The origins don’t really matter, and I don’t care any more whether people see me as a transwoman or a man with a compulsion to feel feminine. I enjoy who I am, and take every possible moment to expand into my world.

Minority stress is not comfortable, but I take some comfort in not being alone in my exclusion. I know that my femininity, like my skin color, is a feature, not a problem. But I have had to accept that for gender expression to be successful, a willing partner is needed. I am disappointed, but philosophical.

I feel free inside, and now the limited opportunities for outward expression in society seem less like a prison and more like a practical living problem — akin to living in a rainy and cold climate and preferring sunshine and warmth. I am also trying to be considerate of people for whom trying to rethink my gender, and therefore every thought and action in their relationship to me, would be burdensome.

Obviously, I can be criticized for not visibly and continuously claiming a place in society. I do take any natural conversational opportunity to politely say that I think we should no longer impose social gender norms on people, but I have realized that my wearing a dress is far more destabilizing for people than it should be, and pushing unwilling people way out of their comfort zone feels like I am wilfully imposing on them.

Thankfully, the pre-trans backlash years did create some room for me to be successfully social: art and theater classes in community college, nominal queer spaces in liberal towns, art museums [is there a theme here? lol] There are some places where a more expansive and inclusive society is alive and well!

But I can see that gender nonconformity isn’t reliably welcome, and won’t be any time soon. It may be coolly or coldly tolerated, but the self-serving justifications of the bad old days of cruelty and suppression are alive and well. And sympathetic people’s fears of rejection enforcements against them,as allies, are perfectly sensible.

I plan my public dress wearing for the spaces where it causes low friction. It feels like standard change management. People can see me but they don’t have to interact. The sky doesn’t fall. A woman is running for President, with enthusiastic support. Society is changing.

Yes, I am lonely. More than a few times I have had warm conversations and been invited to have coffee or lunch, and then it never seems to work out. I think it is simply is too risky or complicated for someone to be seen with me in public.

I have reconciled myself to this. Much as I dream of a vibrant society of people who are unchained from gender rules, I understand why it is so hard. And to be fair, traditional gender rules simplify the choices we have to make every moment we are with others. And most people who have already agreed to live within a set of rules don’t want to renegotiate them.

I have felt that my attempts to connect have resulted in, [using the words of a famous zen koan], ‘the sound of one hand clapping’.

Clapping requires two hands. Gender messaging requires two people — a sender and receiver. Instead of asking for affirmation, I am now trying to give it— to reach out and affirm others, to warmly say hello- to let the magic of the human heart do its work allaying the fears that sustain rigid gender norms.

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Miri
Miri

Written by Miri

We can all help each other a lot by freely expressing our gender

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