I have had six decades to get to know myself, and in that time I have explored, rejected, and re-evaluated a number of self-diagnoses regarding what I do and why I do it.
In my teen years, I just assumed I was the stereotypical “woman trapped in a man’s body”. There seemed to be no other explanation for the fact that I was drawn to wearing dresses, my complete lack of physically aggressive traits or skills (e.g., terrible at any and all sports), my submissive nature that fears confrontation, my submissive nature in relationships, etc. But an active sexual relationship with my girlfriend drove away any doubts on that part: I discovered that I really liked being a man, having sex with a woman. So labels like “crossdresser” don’t really work to well: That usually (but not always) implies an attempt to look like the opposite sex. With my beard, hairy arms, and strong jawline that’s not going to happen, nor do I want it to. As noted above, I’m also most definitely not transgender or transsexual. “Nonbinary” comes closer, except it seems to suggest more a rejection of any traditional gender identity. Again, I’m perfectly happy identifying as a man so that’s not it either. Lately I’m getting more comfortable with the idea of “gender nonconforming”: Yes, I’m a man but I have some characteristics that society has traditionally associated with women. It’s not so much a spectrum (“On a line from 0 at fully male to 100 at fully female, you’re 33% female”). More like a lá carte, where I just randomly got traits from all over the map.
20 years later, settled into a comfortable married life with a wife who, while not especially enamored of my odd clothing choices is at least tolerant without complaining or crtiticizing, I look for other explanations. If I’m not meant to be a woman, then why do I do this?
I rejected the idea of a fetish early on. For one thing, there is little or no sexual element to either my choice of clothing or my response to wearing it. Sure, back in my teens I’d get an erection… but boys are wired to get excited at pretty much anything, so there wasn’t necessarily a direct cause-and-effect correlation between wearing a dress and getting aroused. Nowadays, that doesn’t happen at all.
And yet… it’s not as simple as wanting to wear dresses. If that’s all I cared about, I could be like my friends at Skirt Café who wear skirts and dresses which, while obviously designed for women, are more or less mainstream in contemporary society. Lose the beard and they’d blend in with thousands of women all around them.
But that’s not what I prefer to wear. I’m drawn to the excessively feminine styles of bygone eras – Victorian or even Elizabethan gowns with layers and puffy sleeves and high collars and gigantic skirts; the modest full dresses of the Mennonites and pioneer women; satins and velvets and ruffles; Peter Pan collars on blouses that button in the back; skirts so long you have to lift them up to walk down stairs. And sometimes, in the hidden secret shadows of my mind, there’s an attraction to Lolita-style fashion that I push back against and reject every time the thought pops into my head, because that’s kinky and I’m not a kinky person. Or so I keep telling myself.
Am I? I have a few random theories as to why I’m attracted to the old-fashioned feminine dresses. You don’t have to stay around for all of this. I’m mostly writing it out for my own benefit to (yet again) try to get a better understanding of who and what I am.
One possibility is that I’m trying to return to the era of my childhood. In the 1960s, girls wore those full, frilly dresses. Women, not so much – they had their miniskirts and all, but the girls my age still dressed like Laura Ingalls. In fact, I loved watching Little House on the Prairie because I totally loved those pioneer dresses. I was jealous of the idyllic life those girls led. I was constantly mocked and berated by my peers for my weaknesses. I couldn’t defend myself in a fight; I couldn’t kick or throw or hit a ball in a straight line; I cried easily. But the girls! The girls just had to look pretty and read books and play make-believe games, and I wanted more than anything to be a part of their world. Of course I could not, but I fantasized about it.
Another possibility is my submissive nature. The clothes I like to wear come from a time when women were expected to be docile, and the clothing somewhat enforced that: A girl wearing a big billowy dress with skirts down to the ground can’t be expected to run or climb or fight, so (in my mind) if I dress like that I also can’t be expected to do those things.
The pressure of expectation to be a strong man has always scared the daylights out of me. When the world was too much for me, when I was frightened or sad, I just wanted to be coddled and protected (over the years in my fantasy life, my protector became a strong, dominant woman). Wearing pretty clothes could be my way of retreating into my fantasy world where I can be weak and protected, while someone else makes everything all right.
One last thought relates to a beloved relative who took care of me when I was so small I don’t even remember much about her. She thought I hung the moon, and she brought so much sunshine and happiness to my life (I mostly know this from descriptions that my mother gave me years later). We had to move away and I never saw her again, but sometimes I wonder if in some forgotten corner of my memory I’m trying to dress like her to be closer to her.
The end result is, the things I choose to wear scratch some deep psychological itch that I can’t explain. Maybe one of those ideas above, maybe all of them combined, maybe something else I don’t know about because it’s buried where my subconscious can’t reach it.
Ralph In A Dress 
Another theory may be that in a past life you may have been a woman and that in the present times there is a sub conscious part of your psyche that searches for that prior life.
I am not sure I believe in past lives but I know that some folks do. In my dreams I am sometimes garbed as the women of the 1940s. Other times I am wearing styles of the pre-flapper era, complete with corsets and crinolines. There are even times when my dreams bring me back to the styles that we associate with the 18th century.
When I do dress it is primarily in the styles of women of the 1960-1990 time frame…a bit dated but not totally off the mark.
I know dressing makes me feel better and I suspect it is the same for you.
Thank you for the comments, Pat! It sounds like we share many of the same interests in clothes of bygone eras. I’d like to try a flapper dress sometime, although I suspect it will be difficult or impossible to find something that fits my oversized frame. I also have my eye on crinolines or petticoats to fill out my skirts a bit, but I haven’t worked up enough interest to be willing to spend upwards of $50-$100 on one.
I also try to avoid taking my hobby to an extreme point beyond which my wife can no longer ignore it. She has never been overtly bothered by my drab, monocrhome (usually black) mid-to-late 20th century dresses but I’d rather not find out that I have gone too far. My wife means far more to me than any fleeting pleasure I might get out of exploring an urge to crossdress more!
As for the past lives theory, I’m inclined to dismiss the idea. Why would I only retain a memory of the clothes, and nothing else?
Yup sounds like a psychological quirk. But we all have them, I have been thinking of these definitions a lot lately. I don’t want to be a full time woman, but it’s a step beyond crossdressing. Bigender came up which is closer. Crossdresser+ maybe. For you perhaps just gender fluid works. I mean there is a new term everyweek so something is bound to pop up.