I am tall, standing well over 6 feet. I have a mustache that I’ve had since my freshman year in college, and I’m very reluctant to shave it off, and probably never will. I also have big feet and have never found women’s shoes that fit comfortably or are even bearable.
The questions remain: Why do I crossdress? And does passing matter?
I’ve never found a satisfying answer to the question of why I crossdress. My reasons are some of the most common: expressing my feminine side, feeling more comfortable dressed as a woman, or at least wearing women’s clothing, and feeling complete — my authentic self.
I can achieve all of that without passing, without the need to be out in public successfully passing myself off as a woman. Even dressing at home behind closed doors, I achieve those goals.

Is there a thrill that goes with passing that I’m missing out on? Yes, probably. In my first marriage, I often sat on my front porch in our small town wearing a dress and appropriate underwear underneath. Shrubbery in front of the porch partially blocked me from being seen by people walking past the house on the sidewalk just a few feet in front of the porch. It was definitely fun to sit out there, but the actual dressing was the important part.
In my current relationship and new home, I am lucky to have a very supportive partner. She has known about my crossdressing since before we met (we met online and exchanged lots of secrets in advance of meeting). She has bought many of my clothes for me, especially bras and dresses. I am able to fully dress at home whenever I want. But she is not comfortable with me being seen by anyone else — friends, family, or strangers. Dressing is just for me in the privacy of our home. She’s not turned on by my crossdressing, but neither is she turned off. She accepts it as part of me, knowing that need will likely never go away (over 55 years of crossdressing and the need is as strong, or stronger, than ever).
I’m okay with that. Being able to fully express my feminine side at home satisfies me. Although it would be wonderful to wear a dress while sitting on our back porch, which is very private, there is always the possibility one of our next-door neighbors would see me. I’d be okay with the risk, even if I was seen, but she is not. So I’ve given up on that possibility for the privilege of fully expressing myself in the house, with her full support. It’s a reasonable trade.
That also eliminates the need, whatever it might have been, to pass in public. It takes some pressure off me. And it allows me to focus, to whatever extent I need, on why I crossdress, or if I even need to figure out why I crossdress. I don’t need to worry about my mustache or the fact that my feet are too big to find women’s shoes that are comfortable enough to wear even around the house. Or if I’m wearing something that doesn’t fit me perfectly — although she’s really helpful in finding clothes that look good on me and wants me to look nice, as well as being age-appropriate, in what I’m wearing. So no miniskirts, stilettos, bullet bras, etc., although I’m sure she would indulge me in those if I really needed them. But I don’t.
So is passing important? No, for me, it’s not. But everyone is different. I know there are crossdressers for whom passing is the goal at all times. And I’m not saying I don’t wish I could pass — I’d love to pass. But it’s not in the cards for me, and I’m okay with that.
Great topic and one of the common threads woven into the giant CD blanket! For myself, I do not give any thought to ‘passing’. To me, that word means the notion that you think you’ve convinced others (strangers) that you are a cis female. Firstly, how could I know what other people are thinking? If I have that super power, this seems to be a poor use of it lol. Secondly, they’re strangers – devoting that much of my energy to the feelings of people I’ll never talk to, let alone see again is more energy than I have. And… Read more »
Thank you so much, Melodee, for your thoughtful response. I like your statement in your story, “Well if I’m gonna be tall no matter what, lemme be extra tall!” LOL I got my first pair of shoes just a week ago after I had already submitted this article. I went with flats; I’m not opposed to heels, but at my age I’m not sure I need to learn to walk in them. But the thing is, crossdressing is for me, not to pass, so if I did happen to find heels that fit and are comfortable, I’m always free to… Read more »
Get’em, girl! You the heck out of you! 🙂
Passing and looking good are very important to me. I like going out as a girl. I do not want to get jumped. You are correct in stating that: worrying about what strangers think is a waste of energy. Nevertheless, I still wonder & worry what strangers think. My girl confidence is a rollercoaster. Lol!! This year I have been out over 12 times, and I still get nervous.
Thanks for your comments, Tracy. I’m not disparaging anyone who can or who wants to pass — more power to you! I’ve just come to terms — for me — that I’ll never be able to pass, and I am okay with that.
This is a great topic and great thoughts. I don’t pass well, so when I go out, I have to accept that I’m going to be “the guy in the dress.” I think I look pretty nice generally, but I know I’m not fooling anyone. I would like to be able to pass just to avoid the stares and giggles and such. While most people don’t care, there’s always a few that pay more attention to me than they normally would. It would be nice to be seen as just as a normal woman when I’m dressed up. I do… Read more »
Girl…I just looked at your photos. You are rocking every look. But no one can convince you, except you. I can guarantee you that 95% of anyone you hear giggling/chuckling/etc has nothing to do with you. And the other 5%? Well who cares. Easy to say, yes, but start putting it into practice and you’ll be pleasantly surprised at how quickly it takes off. 😉
Thanks for your kind words Melodee. Your photos are also wonderful. I completely agree, that not worrying about what others think is a learned skill. Usually I do pretty well and feel great, but every once in a while something happens that shakes me a bit. I suppose that’s good for me. But it would be nice to enjoy a favorite outfit/look without having to go through the effort of ignoring others.
Thanks, Sarah, for your comments. Oh, to be “ignorable.” That would be wonderful, indeed. And it would take all the pressure off of the effort to pass. I haven’t thought a lot about the deviant aspect of crossdressing, but I can understand the attraction there, also. Maybe that’s why I do selfies so often in everything I wear? There is something to be said for being a little weird LOL. But blending in works better if we’re trying to pass. I also feel the same way you do about not being trans or wanting to become a woman. That’s not… Read more »
Hi Sarah. I’m 100% with you on this. When I’m dressing for photos I’ll go the whole hog and try and look as feminine as I can, but when dressing to feel more me then the image in my head is all that matters and feeling like I am the attractive woman in the catalogue is where my head is at. I do so want to go out dressed more and not worry about stares and giggles, but like you, I can’t help that I do. It almost feels better, or perhaps more authentic, to be a man in a… Read more »
I agree with the authenticity point. Since I’m not transgender, I don’t feel a need to be recognized as a woman, but it would still be fun if I was prettier! In many ways dressing up has made me more confident, or at least less concerned with the opinions of others. I think on the whole, I like myself more when I can dress up from time to time.
I can’t pass when I lived in Florida our house had fence so I could walk around the yard or sun bath it was great and I do have the fear of being caught my wife kind of knows
Thanks, Nicole — when we were looking for our retirement home two years ago, we considered privacy to be a significant factor in properties we were looking at. However, the one we ended up buying, although neighbors can’t easily view our backyard, it is possible, and too much so to be comfortable being outside crossdressed. But other factors were even more important, so we live with the compromise. Life is full of compromises, isn’t it.
Well Trace, you seem quite content with what you have and the acceptance of a partner. It is a refreshing article that may put others who are like you at ease as there are no rules here on how, when and where you should dress, the key is happiness and contentment living within your own boundaries.
Thanks, Angela, for your compliments. You understand well where I’m at in my life right now. And it’s a very good place.
Passing is a passing issue for me. Most of my dressing is at home, from neck down only. But when I go out in public I spend hours preparing, hoping to look my feminine best and doing well enough to blend in without being noticed by many. It is a high to believe that I have succeeded in my feminine skills to the point I am viewed as a woman rather than a man in a dress, and a thrill when complimented on feminine appearance or actions Clearly some do believe I am a woman and treat me that way,… Read more »
Thanks for your comments, Rhonda. Dressing from neck down is what works for me, too, but in my case, it’s all I want or need to do, so that pretty much rules out passing. I’m not looking to be seen as or treated as a woman. I have a website called “Man in a Dress,” so I’m okay with that term, too. But for me that means dressing just at home. Absolutely no disrespect to those for whom passing is important!
neck down is all I want or need if not out, so we are alike. Going out in public, though, is far more fun… a whole different experience with thrills I never could have imagined had I not done it.
I don’t put any value on passing, but do try to look my best. I dress for myself, but do love opportunities where I feel safe to get out in the world.
Thanks, Mysti — I might feel the same way if I found opportunities where I felt it was safe to get out in the world. But I don’t feel I have those opportunities where I’m at right now.
I know that I could never pass on the street. Sometimes I feel like I can look pretty good in photos if I use enough smoke and mirrors. I feel like it would be such a rush to step out in public if I could pass. At one time I seriously considered it but I know that it will probably never happen, but that might be ok. What I enjoy the most is hanging around the house wearing whatever I feel most comfortable in, be it a skirt or dress or leggings. At home I seldomly wear makeup or a… Read more »
Thanks, AnnaBeth, I appreciate your comments. I’m with you; “only so much one can do with the human body that we were given.”
I’d like to think that in the transgender “spectrum” all of us fall at different points. Some like yourself Trace, like to enjoy the trappings of femininty without the added need to “pass”. The important part is that you are comfortable with where you are on that spectrum, and it seems you are. You are gaining the benefits of our proclivity, you own it and are the better person for it! No one can tell you what you should or should not be experiencing – it is different for all of us. And if you get right down to it,… Read more »
Thanks, Kris, well said. One thing I’ve learned over the years is that all of us are different and at different points in our transgender or crossdressing experience, desires, and needs. And that’s okay.
When I’m at home, I will wear whatever I want, with or without forms, wig, makeup, or anything else. But if I’m going out in public, which I often do, I want to “pass.” But I learned early on that passing doesn’t necessarily mean fooling everyone or even anyone. My first time out after a makeover, I went to a diner and the manager asked us how everything was. My friend answed, but then she asked me as well. I was forced to answer. Even though I didn’t use a masculine voice, I’m sure she knew. But I was accepted,… Read more »
Thanks for sharing that, Alison. Good perspective on what it means to pass. I think you’re right.
YES! I love your perspective: it’s not about “fooling” anyone, it’s about being accepted for who I am and how I am choosing to present. For me, of course; everyone’s personal perspective is valid.
You are lucky in that you have found a comfortable niche in your dressing life in which you are content and happy. Many CD’s are never able to reach that point for one reason or another. My situation is different in that I live full time as a woman and am constantly out and about. For me, passing is important. It makes my overall dressing life much more pleasant and interesting when I’m treated as just another woman when out in public. It makes me more relaxed and better able to enjoy the experience by not having to wonder what… Read more »
Fiona, thank you for your comments. I have always admire your “conviction” to live full time..yo are an inspiration for ladies, including me, to be our true selves.. for now, I try to pass, maybe, to emulate a woman, most definitely…
Thank you Leonara
Thanks, Fiona, for sharing. You’re right, I am lucky. I’m also glad that you’ve found success and happiness in passing. I mean absolutely no disrespect to those for whom passing is important. If I had the choice, I might do exactly the same as you. But my dressing life — and need to dress — while compelling, is different from many others. And that’s okay.