I recently reached a crossdressing milestone in my life. Twenty-five years of going out dressed as a woman, or more accurately, going out as the woman I feel is within has recently given me cause to reflect on those experiences. I’m talking about being in a public setting where I am not in control of who I may or may not run into.
Like many of us, my dressing began in private and remained that way for many years. Walking around in heels and a skirt in a safe place was only partially satisfying, and so I had resigned myself to a life of closet-dressing. I attended group meetings where several of us rented a large hotel suite where we were able to dress and hang out together. We were all pretty much in the same situation. As much as I enjoyed this, it seemed as if it were only a much bigger closet; I wanted more. Slowly, often very slowly, I went out more, often in the comfort of other crossdressers, and always taking care to be very discrete. I would look over my shoulder and carefully observe my surroundings, hoping not to cast too much of a shadow.
With time, I felt as if I could pass. I became more comfortable going shopping and dining out. One could say that practice makes perfect. The routine of going to places and doing activities, especially shopping, helped me find a level of comfort. My excursions have been very enjoyable and uneventful and rarely have there been much in the way of interactions with people when out. Again, I have been somewhat invisible, so to claim I was passing may not be accurate, especially if my presence was hardly noticed or not at all.
There were circumstances where interactions occurred, mostly with women, but also men, and they allowed me to become more confident, at least I didn’t feel the need to avoid interaction, and I actually found it interesting, delightful, a part of the feminine experience. One time a woman approached me while shopping and asked my opinion on something, I wanted to look around to see who she was talking to. Rather tentatively, I gave my opinion. She was delighted to carry on with the conversation about the selections, color choices, and apparently oblivious to my presentation or didn’t care in the least. It was the first of many, and each one that followed became a little easier. Over time, it presented to me a feeling of validation that I was real. Not only real but worthy of being there, as well as being seen and heard.
Recently, I had an opportunity to meet with a friend who is much like I once was but wants to branch out and live more freely as herself. We met for coffee and immediately she wanted to know how I could do it. How could I just walk into a department store, try on clothes and shoes, when I was taller, had a deeper voice, etc., without being scared? What I told her was that it’s perfectly okay, and in most cases, no one really brothers trying to determine if she is really a woman, if they even noticed her at all.
She wasn’t buying my advice and couldn’t relate to my experience. I invited her to go shopping with me. Reluctantly, she agreed. She did browse and found a couple of items, but she could not bring herself to go through the checkout, instead, asking me to pay for her. It was clear that she was much more nervous than I realized, and she didn’t think she would try it again.
I really wanted to help her, feeling as if I failed her by not relating how my confidence had been gained over time. What could I say or show her that would help her gain that same confidence and enjoy herself fully as the woman she felt she was?
I’m told that I pass very well, and as such, I try to dress and act appropriately for my age. I ask myself what it is that allows me to successfully go to the grocery store, shopping, etc. What can I pass along to my friend? Passing is a big part of it, but I see women whose appearance suggests less effort at being deemed to be dressed age-appropriately. So, part of the answer is not in passing, but in one’s confidence. Having the capacity to show up however you desire. In no particular order or level of precedence, this is how I am trying to help my friend achieve her goal of going out in confidence and safety.
We are somewhat fortunate to live in a time where being dressed in the clothes of the opposite sex is no longer a violation of the law. Culturally, it is still at odds with what many people expect.
Take care not to stand out too much. If you are going to a familiar place, take notes on what women are wearing in those places. A Cis-woman can get away with wearing almost anything, but for a non-Cis woman, something comfortable, not fussy, or unmanageable is best. I love getting a bit more dolled up and glamorous, but I avoid stopping by the hardware store or garden center in heels.
Familiarize yourself with the places you will go to. Maybe even visit them discretely while in male mode to learn what the place is like or when the best time is to visit or is it crowded, who are the clientele. It has been my experience that I received more acceptance and felt more comfortable in places where I was mostly in the company of women. Women have noticed something that might give me away, but they have always been discrete about it. I have also witnessed men who have seemed somewhat uncomfortable, but nothing happened.
Pay with cash if you are uncomfortable tendering a credit card with a male name. Smile! Women often smile and greet other women, so be prepared to return the smile.
If concerned about catastrophic circumstances, car trouble, unable to return home incognito, carry makeup wipes and a change of clothes.
Check for gender non-discrimination support in-store policies and local ordinances. There is no guarantee, but many companies provide training to employees to avoid discrimination. In the beginning, visit places that have inclusive policies.
Last but not least, it’s likely that you won’t experience violence while shopping; it is still a possibility. It is necessary to give it some consideration.
Several of my first outings were Halloween and Costume balls. There was no question that I was en femme and obviously crossdressed for all the world to see. It was somewhat desensitizing being seen that way as if I were part of a joke or gag. It did give me an opportunity to gain some of that much-needed confidence.
Be confident, be yourself, and maybe you’ll have some wonderful experiences of your own to share.