More of Sylvia’s Journey

Return to A Cross-Dresser’s Journey

The stages and epiphanies of an MTF (male-to-female) cross-dresser’s journey are poignant, significant, and, for many, tend to follow a pattern. Most importantly, there’s the first time wearing clothing meant for the other gender. Then there’s identifying the newly found feminine persona with a “fem” name; assembling a wardrobe that says much about the individual style of the cross-dresser; the first time out in public and dressed with the intent of “passing/presenting” as female; acquiring enough skill at passing to occasionally go out, carrying on everyday activities. For me, a complete, perfect girl’s day/night out would be the hair and makeup salon, shopping, lite lunch, then an afternoon at an art museum, sometimes followed by an evening at the theater. I’m tall, so passing is not easy, but I try. Finally, I’ve evolved to an activist stage where I want to do outreach—educating others about the “T” part of LGBT.

Choosing a particular style depends on individual taste, and results in a defined image—a reflection of how cross-dressers see themselves and want to project in public. Younger “dressers” are generally more informal—athletic gear and pants are commonplace. I did not survive all the pain, confusion, and guilt on my journey just to wear pants, so for me it’s strictly skirts and dresses. My own style is an interpretation of a glamorous retro ultra-fem ideal. Someone once described my look as “River Oaks Realtor,” and that is a good, uncomplicated assessment. There are bittersweet moments, like reflecting on a time years ago when I could have been a “babe” without the proverbial pound of makeup, but was too frightened to go out.

“Age-appropriate” can be code for “You’re older and should dress accordingly,” meaning dowdy. I believe if a girl can still carry it off, she should dress however she wants, within the bounds of decency. A traditional cross-dresser does not do “drag” or dress in a way that demeans women. My favorite story on age-appropriateness appeared in the fashion section of The New York Times. An older lady of means was walking out the door of the Manolo Blahnik boutique in New York. Outside, a large Mercedes with a driver waited. Before exiting, she turned, held up a pair of stiletto heels and announced to the store, “At last, I found a pair of shoes that fit.” A girl can’t go wrong following the fashion section of the Times.

My most poignant discovery on my journey was not in the superficial (perfecting my passing ability or honing my fashion edge). It was discovering who I am as a person…a transgender person. First, there was the realization that I was a transvestite—something that was supposedly “cured” with electric shock in the ’60s and ’70s. (They’d have to catch me first!) The most hope and support in those days came from advice columnists Dear Abby and Ann Landers, who increasingly showed compassion and enlightened thinking regarding cross-dressers. In responding to a cross-dresser’s wife who expressed concern over her husband’s cross-dressing (which I did secretly for many years), one of the columnists responded, “Your husband is probably a cross-dresser, which in many cases is a benign and harmless activity. If so, there isn’t a problem unless you make one.”

In college, I learned from my 1970 Abnormal Psych textbook that cross-dressing was a character disorder. The book cited the success of “aversion methods” and shock treatments (Blakemore, 1963), but it also mentioned the work of Carl Jung. The Jungian paradigm notes that no man is entirely masculine nor any woman entirely feminine, so we must find these elements in us and become more complete personalities. My traditional “male” way of approaching problems was different from what I learned in Jung. I found a part of me that listened, was compassionate, and acquired what was seen by some as feminine wisdom—all things that society considers “deviant” in a man.


For me, clothing became a way to access Jung’s “anima,” the feminine, and to round out my personality in a culture that still has definite views on what a “man” should be like. Various cultures handle this topic differently. In Japanese culture, cross-dressing Kabuki performers have a revered place and are so expert in the feminine that genetic women seek their advice. Jung helped me with self-acceptance and family acceptance. I frequently attend lectures at the Jung Center on Montrose, where they have a list of approved Jungian analysts available to contact. It’s about reaching a balanced, psychological construct with which to understand the desire to cross-dress.

To play, have fun, shop, try the latest makeup colors in from the coast…it’s all relaxing and good. This is a good segue into the “compassion” aspect of giving something back. Eventually, I would like to consider talking to PFLAG and other groups that deal with young people who are cross-dressers and sometimes misdiagnosed as gay or something else. Every year, there is an evening ceremony for “The Day of Remembrance” when transgenders who have been murdered are honored. There are many disturbing and sad stories of young cross-dressers who were caught “dressing” and beaten by the father or another male to make them a “man.” Education and outreach must be a priority in the community.

How does American society view us? Usually as comedic or dangerous. In film, for every positive movie like Albert Nobbs, there’s Dressed to Kill and The Silence of the Lambs. Major retailers see how much money can be made from cross-dressers and have educated their sales staffs to be welcoming and accommodating…and to sell. I’ve seen sales staff go from disapproving looks to a cheery, “Hello! Yes! May I help you, ma’am?” If I have an especially good shopping experience, I always thank them for their help and professionalism.

So, being the “T” at the tail end of “LGBT,” how are we treated within the community? From my experience, overwhelmingly good—and I’ve met many prominent community people like Ray Hill. However, once I was meeting some “gurl” friends at a Montrose bar. An older man came up to me and said emphatically, “Who are you? This is a gay bar.” My reply: “And it is a bar licensed by the state of Texas, meaning as long as I’m behaving myself, I have a right to be here.” Another time, a greeting from a stranger turned into a conversation that made me increasingly uncomfortable. Edging closer, he finally said, “Do you ever worry about your safety?” Using my best tough-broad voice, “Not really! I keep a Smith & Wesson .357 ladies model in my bag.” I don’t own such a thing, but it was almost comical seeing this person beat a hasty retreat.

Thanks to OutSmart for this opportunity to share, and also to HTGA (Helping Transgenders Anonymous), Tri-Ess/Tau Chi, the national and local support group for cross-dressers and their spouses, and to my wife, who took the time, love, and understanding to share this adventure with me.

Sylvia’s energies show no sign of diminishing. In fact, she has discovered an alter-ego, “Miss Sooo Divine”—an older woman who was the 1967 Miss Vegas Cabaret Singer. She still sings in the karaoke venues of Houston’s inner city and knows that nothing can compare with the sparkling gowns, the stage with a microphone, the lights dimming and an MC appearing to repeat the famous words from the dance contest in Pulp Fiction: “Young lady, what’s your name? … Miss Sooo Divine! … All right, let’s see what ya can do. Take it away!”


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