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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!
@mkat3874 I simply cannot tell a lie - I your take (Tiffany) on strangers passing comment on outfit & makeup choices with my mouth wide open. Are some people for real? How very dare they! Ouch. I think you're right with your sentiment they're possibly bitter about their own lack of confidence to be their true selves.
A fabulous read - some brilliant insights thanks both so much for taking the time to write this!
The day that my coworker told me my shoes were not appropriate for my age I went straight home and ordered another pair in a different and even more vivid color.
@mkat3874 Good story about passing and worrying about it. I think I pass pretty well. I have been working Walmart for 2 months now and yesterday I was working near the front doors almost all day. I was asked to help customers so often. I have not been been called she her and ma'am so many times in just a few hours.
Cassie
@mkat3874 What a great article. Thanks to both of you for writing it. I feel like my wife and I are right on the same path as you both, just a few years behind. We are trying to catch up!
So happy to hear that there are other couples having fun together. Just enjoy the journey.
Hello Michelle,
It was a pleasure reading your article, passing in my opinion is beyond our outfit, makeup and all the accessories. It has to do with our attitude, not worrying too much about other people’s opinion, we just have to conduct ourselves like a natural woman.
Now with all that said, I did take a quick glance at your profile photos, you look amazingly beautiful, your selection of clothes is just excellent, love every single one of them, congratulations on being yourself.
Carla
Thank you Carla. I must give Tiffany credit for helping me so much. She has an eye for what works well and what doesn't. When we are shopping she will show me something and tell me it would look great on me and I just don't see it. When I get home and try it on I'm pleasantly surprised with the result and can't wait to wear it out.
Thank you both for a thought-provoking article. Also, I cannot lie: Both of you are truly gorgeous in your photo. So beautiful in fact that I had no idea which of you was which until I saw Michelle’s profile page. Maybe that just underscores your points.
Thank you so much but as you may now know, the photo used for the article was a stock image selected by the editors and is not us. I'm glad you were able to see our actual pictures. For future articles I plan to provide a picture along with text.
So happy for both of you ! Your love and support for each other is uplifting . You both are beautiful ladies .
Jeanette
This is a wonderful article...thank you!
XO Shawna
I absolutely love this. I read an article not long ago that offered the concept of focusing on being "presentable" instead of worrying about being passable. It ties directly with your thoughts on putting care and effort into how we look as we go out into the world. When we are confident in our look, everyone senses it.
Well said, ladies!!!
@aprilrhaynes You are so correct April, taking a little extra care to look nice greatly increases the odds of being accepted/tolerated by members of the general public. When people see you taking care of your appearance they are more likely to react positively to you. Also, it increases your confidence. That confidence is sensed by members of the public, making it a bit easier to be accepted as a CD/Trans person.
It's a never ending feedback loop.
Thank you for your combined perspectives.
At the moment, I can't pass. With my male head, I know that, at best, I will confuse observers, so I don't go overboard with wearing female clothing. For now, I accept the compromise.
"Do your best, look your best, and be your best. If you're happy with the result, congratulations. That's the only standard you need to meet to pass."
Thank you for that article and that wonderful summary statement. Granted, it is not easy but it certainly is helpful. At the same time, we have to be honest with ourselves so we are not presenting poorly which then can be reflected in other's opinions about crossdressers. I think that we should have some concern about the impressions we make even when we satisfy ourselves. Thanks for the well- written article.
Thank you Carla. One thing I've picked up on as we've gone out with our CD group over course of the past year is that when we are in public and striving to be the best versions of ourselves that we can be, we are treated as we are trying to present. I wouldn't dare pretend that a group of 8-10 CD's would ever be perceived as genetic women but we are treated like ladies when we present as ladies. Who knows what may be said after we leave but that's nothing I should spend time concerning myself with.
Some very interesting writing here! Nice to get the perspective of the two of you and I hope you'll continue to offer them.
Thank you Jennifer. It was fun to write this with Tiffany. It gave us the chance to talk deeply about this and a lot of other related ideas. I would enjoy doing it again in the future.
I have made this comment numerous times and I hate to be that person, but I truly feel it is central to finding happiness in life in general, but for CD/TG people especially.
The concept of 'passing' is the idea that 1) you can directly affect how strangers perceive you; and 2) that you can afterwards know how successful the first part was.
People are going to think what they want to based on their years/ decades of experiences and opinions. One's ability to have anything more than a minor impact on that is quite small.
I can almost guarantee that everyone here has seen a person in their lifetime and thought, "Is that a man? Is that a woman?" despite every effort that person made to appear as one or the other.
Further, how can you possibly know how successful you are at this? Even if you asked people directly, the answers given may be untrue out of politeness. So you would still walk around with this doubt of how well you were "passing".
Someone's reaction to you says everything about them and nothing about you. Period. So just get out there and be the youest you that you can and leave other people's opinions to them. 😉
@melodeescarlet I am pretty sure I've heard you talk about this. 😀 And you are so right. Once I found confidence in myself and my look, I stopped worrying about passing. If I feel good about my look and style, that's what matters.
@melodeescarlet I agree with your sentiment however ...
I think what some people want when they use the term "passing" is "to go unnoticed", to not stand out in the crowd and mainly to avoid confrontation or harassment.
@butteryeffect I do understand that, but I think that's effectively the same. 'I want strangers to think...' Your ability to affect whatever you put at the end of that sentence is going to be incredibly limited.
I've noted before that of the three parts of the process of going out - 1) How you look; 2) Where you go; and 3) How you act - the third one is, in my opinion, by far the most important.
So just dress in whatever manner makes you feel best about yourself, and go to the place that you want to go, but behave like it's just any normal activity. I feel it's this that people pick up on the most, not how you look.
@melodeescarlet Right on! Part of me "passing" is just being myself. If I am in "hybrid" mode and wearing a skirt and have painted nails, then I'm passing as hybrid. People can either take it or leave it. I get the sentiment to just dress full femme and be left alone. But I think what you says is spot on.
Thank you Melodee. As we were discussing and working on this article one thing that became clear to me was that my concern for passing was really a reflection on my confidence or lack thereof. We've only been going out for a little over a year but I can certainly tell that my confidence has been growing with each time out. One way I can see it is in how I dress. The more I go, the more vibrant, colorful, and stylish my chosen outfits have become. On my first couple of times out I literally dressed to try to not be seen -like that was even possible. Looking back it's funny now.
@mkat3874 Good for you! And, yes, confidence is built - each repetition adding another layer until you have a solid foundation! Keep at it 😉
Thank you for taking the time to write an informative and relating your experiences of sharing being out together.. the “holy grail” of any crossdresser is passing.. I believe we are our own worse critics even though we may receive favorable comments on our feminine presentation… like Michelle, I too, question if I pass … however, as a a mature crossdresser to blend in and dress appropriately was my objective when I unlocked my hotel door for Leonara to see a sunrise on a Florida beach ..since it was a chilly morning for Florida, skinny pants top and my unisex jacket, wig, lipstick(of course), earrings rounded out my feminine presentation… the walk to the beach was 6 blocks with cars passing by and other “sunrisers”… I was so into the moment, I really didn’t notice any criticism as I took photos of rising sun on the beach… thank you for listening…Leonara 🌹
Thank you Leonara. As I've grown in confidence my willingness to walk in public apart from the "safety" of my CD has increased. Just last month Tiffany and I spent a couple of hours in our own at a museum among quite a lot other visitors. I was surprised to see that there were no obvious stares or comments that I could tell. It helped me gain even more confidence to step out even further the next time.
Great article.
And you are both absolutely stunning!
Joanna 💕
To add one more comment...there was a time when I would constantly ask my friend who works in a women's clothing store, "am I too old for this style?" to which she would always respond: "if it speaks to you, then you're just the right age to wear it!" I so appreciate this post, especially Tiffany's contribution. Thank you both, again!
XO Shawna
I agree with your friend. Don't be afraid to wear what makes you feel your best.
Thank you for such an interesting article. I know we have our own considerations as to 'passing' with that constant niggling inside about looking right. I was exactly the same and asked girls who I knew well what their opinions were. Most wer 'you look great, stop worrying' to one who said'You look fine and if you didn't I wouldn't be here with you'.
The other aspect you highlight is that woman themselves can be harsh critics of other women, something I have witnessed when at work.
So if you are confident and look acceptable the rest will follow.
Thank you Angela. Its great to have friends we can call on to ask their advice.
So interesting to see a story from both points of view. One of the most interesting things about being a trans woman has been that I have been able to view the world through the eyes of both a male and a female. And I much prefer the female view.
My goal was always to pass as well as I can while I'm out in public. Doing so allowed me to fit into society very nicely and very rapidly. My first time out was May 2022 and I decided to live full time that Fall, five months later. I only decided to live 24/7 after realizing that my efforts to pass were going well. I would say 80% of those who see me while out without any interaction believe I'm a woman, 10% are unsure and 10% know I'm trans. I can live with that. With a quick interaction like just a "thank you" I sound female most times but anything more than that and I'm outed. It took a lot of work with clothing, makeup and mannerisms to pass and blend in but it was well worth the effort.
Fitting in and not having to worry about how I looked has helped make my trans life a very pleasant, fulfilling experience. It allowed me to become confident early on and that confidence has grown be leaps and bounds ever since.
Personally I feel that "passing" is something about 2% of us can do. If you are not blessed with the right bone structure, nice hair that you can grow out, a slim almost petite figure and good skin then the world will see past all we do and recognize you at some point for being in disguise.
I think for most of us we should be blending in, trying to look as feminine as possible, present in the best possible way and be accepted as part of the world. Being able to live my life and go about my business as a woman is my goal. I'm many of the things that people think aren't a woman. I'm too tall, too heavy, wear wigs and too much makeup (a must unfortunately). I can get by in most situations but on close inspection no one is going to really think I'm a natural born woman. That's ok too as long as they accept me as a person and don't view me as a freak.
I'd love to pass, but most of us just can't and we need to live the reality.
TBH, when I go with Michelle to the CD group meetings and we're out having a meal with the group I will be deep in conversation and often find myself feeling like we're just a group of girls out having a good time.
Blending in is fine if a girl is satisfied with that. I have written a column on just that (or not) elsewhere and my thoughts on it haven't changed. Yes we are men and nothing will change that but we can surely dress up to give some color to our lives upon occasion. None of us will have the petite body, narrow shoulders, 70% waist to hip ratio, etc. But to that I say - so what. Genetic girls go around dressed as men for much of their lives so what's wrong with a guy dressing with some style and color so that he/she gets noticed in public? Drab is boring, nothing will change that. See my forthcoming article on that in May.
I have a stylist at Ulta who I have become great friends with.Her and I go to bingo,out shopping and we even have girls night and watch movies.She reigns me in and tells me what she thinks.She thinks I am extremely passable.I have a hard time believing this at times.She is such a great woman and has been so supportive as have many ladies here also.
