I am co-writing this article with my wife, Tiffany Kaytee, who has recently joined CDH. The idea for the topic came from a recent conversation between the two of us. Tiffany has been fully accepting and supportive of my cross-dressing since the earliest days of our 28 years of marriage and for that I am incredibly grateful. We have been going out together in public, monthly, for a little over a year now and we have lots of fun each time we go. She has helped me immensely over the past few years in developing and refining my feminine presentation. From shopping with me for clothing that works best with my body type, to assembling the final ensemble, she has been an invaluable guide in the feminine arts. I would also be remiss if I didn’t give credit to my eldest daughter who is extremely talented with cosmetics. I shudder to think where I might be without their treasured support.
From Michelle’s point of view:
I spent decades dressing in the privacy of home, dreaming about some day stepping out the door but not at all concerned with how I might be perceived in public. Once I finally reached a point in my life where I felt ready to venture out of the comfort and safety of home en femme, I started to give serious concern with how I might look to others. The essential question being, would I pass? I realize there have been numerous writings on the topic of passing, published both here and on many other platforms. The intent of this article is not to review what has already been said on the topic, even though I do think many who cross-dress and venture outside wonder about their potential for passing, but to ask: should I care, not care, is passing even possible, or does it even matter as long as I’m living my best life and we’re both happy?
A few months ago, Tiffany and I were in the car, about to set off on our way for a girl’s weekend outing, when I casually asked her if she thought I passed. Prior to this point I had not asked her specifically about passing. I had asked her many times if I looked “OK” or “presentable” and each time she lovingly reassured me that I looked fine. I’ve come to appreciate that she has a keen eye for style and would never knowingly let me make a critical blunder in public. This time, however, I wanted to know if she thought I “passed”. She responded casually with, “Sure, you look great.” Overthinking things as I usually do and not sure of her answer, I said, “Really?” Again, she said, “Yes, stop worrying about it and just have fun.” Still overthinking and not completely satisfied with her answer I gave up the interrogation and we went on to have a great time as always.
On the morning after our weekend outings, we like to spend time reminiscing about the events of the weekend and after the weekend in question, I took the chance to ask her once more if she thought I had passed. This time she responded by asking me if I thought she had passed over the weekend. I was caught by surprise as I found this to be an extremely unusual question coming from a genetic woman, and a gorgeous woman I might add. How on earth could she even possibly question whether or not she passed? I began to suspect that our ideas regarding what it meant to pass might not be the same. To be clear, I don’t believe at all that I would be passable beyond perhaps casually walking past someone in public where no interaction occurred. Even then, I’m not sure if I actually could. If I were to speak or exchange more than a momentary glance, passing, in my sense of its meaning, would be out of the question. My goal for passing is simply to blend into the public background becoming essentially invisible or at least unremarkable. Tiffany, on the other hand, has a very different idea about what it means to pass. She will offer her thoughts from this point forward. She doesn’t claim to speak on behalf of all women or any other woman, but only for herself.
From Tiffany’s point of view:
As Michelle said, I see this topic from a somewhat different point of view. I am a middle aged woman, a wife, a mother, and a grandmother. Society has established a set of unwritten rules for women regarding how we should present ourselves in public. I like to call these rules the “girl code” which says that we should present ourselves in a way that is appropriate for our age and if we dare to step out of line someone will take the self-appointed authority to let us know we’ve violated the code. This has actually happened to me on a variety of occasions. For example, I was told by a co-worker that my particular shoe style wasn’t well suited for someone my age. On another occasion, an older woman approached me in a grocery store with a scornful look on her face to ask me if my choice in makeup was what people were wearing these days. To be clear, I certainly do not dress provocatively and I consider my style to be generally conservative. However, I love bold colors, vivid patterns, glitter, sparkle, eye-catching shoes, fun glasses, and statement jewelry to compliment my outfit. I love to dress up for no particular occasion and I truly feel my best when I look my best. I see my dressing as an extension of my personality: energetic, playful, and joyful. I work as a nurse and I have to wear boring scrubs at work. The only freedom of expression I have there, is in selecting my own shoes so long as they are not open toed and I can wear them comfortably all day. I am one who considers it a treat to get dressed up just to go to the grocery store on my day off. Passing for me, considering the girl code, means I have to conform to the unwritten rules, being careful not to be too expressive in my style. If that is what it means for me to pass then I don’t want to pass. I want to stand out.
The truth is that most of those who might call me out on my style choices secretly wish they had the confidence to do the same. I’ve been encouraging Michelle not to put too much focus on passing. If I can’t even feel like I pass, then she shouldn’t spend time worrying about it either. The world is going to look and they are going to judge. I say give them something to talk about. Do your best, look your best, and be your best! If you’re happy with the result then congratulations, that’s the only standard you need to meet to pass. I understand the nuances of passing for genetic women aren’t quite the same, but in either case, passing should not be about meeting some arbitrary social standard or trying to hide in plain sight, but it should be about having the confidence to enjoy the moment, express who you are, and have fun.
Since going out with Michelle this past year, to our cross-dressing group meetings and weekend outings, I have had the chance to meet a variety of different and beautiful cross-dressing persons. I admire their confidence and the effort they put into looking and being their best. When we all go out together, one thing I can count on is that we will be the best dressed wherever we go. The older I get the more I realize just how precious every moment is. I don’t want to find myself in my later years regretting not living my best life and enjoying it to the fullest with my best friend.
Happy dressing ladies!
Latest posts by Michelle Kaytee (see all)
- A Reflection on Passing – a woman’s point of view - April 5, 2025
- Year One - January 19, 2025
I learned a lot about passing in my few outings. After my first makeover, I went out to the local diner with the woman who ran the transformation business. When we were leaving, the (woman) manager asked us how everything was. I was relieved when my friend answered, but then the manager directed the question to me. I gave her an answer in my little practiced feminine voice. I was relieved at the time, but when I think about it in retrospect, I think she knew, didn’t say anything, and didn’t care that I was male. About a year later,… Read more »
Thanks Alison for sharing that story. When we go out with a group of other CD’s we’re not fooling anyone but when we are dressed and looking our best we are treated as we want to be treated. That reminds me of a funny story. Back in January we all went to a restaurant that we go to a few times a year. They know our group well there and we always have a great time. As we were being seated one of the waitresses said to us that she just loves it when the tall girls club comes in… Read more »
Many thanx to putting a label on it i.e. “the girl code". To me the “code" has resulted in women being a bunch of wimps-running up the white flag so to speak.And many kudos to you to buck the “code". Most usually I wind being the most “overdressed" wherever I am but do get a lot of compliments from women. I have wanted to say “so why don’t you dress up"? I guess I would have wasted my time as the girl code seems to rule
As I see it, there are two types of “passing". The first is you look like a genetic woman, and there are a surprising number of ladies here who…at least judging by some of the pictures posted here. No doubt that is every CD/tans persons ultimate dream. The reality is my second type of passing, and that is looking enough like a woman that it makes people wonder, or, and more importantly, it makes us look enough like a woman that we are accepted as woman even though others know, or highly suspect we are male, or possibly trans. This… Read more »
Wonderful article, words to live by! Thank you both