Why Do Crossdressers Like Short Skirts?

If you look through photographs of crossdressers, you may notice that short dresses and skirts appear often—sometimes very often. Not every crossdresser favors a high hemline, of course, but enough of us do that the question deserves an answer: Why?

The simplest answer may be the best one: If you have the legs, why hide them?

Many crossdressers consider their legs one of their best features. Men often have long, relatively slender legs, and hosiery and heels can make them look even better. A short skirt puts those assets on display. When someone has spent years worrying about broad shoulders, a square waist or other masculine features, discovering that she has a very attractive pair of legs can be a welcome confidence boost.

I know the feeling. My legs have received more compliments than any other part of my feminine presentation. My mother used to tell me that I should have been a girl with legs like mine. Other women, including my wife, have complimented them, too. After hearing that often enough, covering them with a floor-length skirt would almost seem ungrateful!

But showing off attractive legs is only part of the story.

Unmistakably Feminine

For many of us, a skirt represents femininity more powerfully than almost any other garment. A short skirt turns up the volume. It looks, moves and feels unlike anything traditionally found in a man's wardrobe.

That difference matters. Crossdressing is not merely about covering the body with women's clothing; it is also about experiencing femininity. The swish of a skirt, the feel of hosiery, the click of heels and the need to sit or bend gracefully all contribute to that experience. A shorter hem makes us especially aware of how we stand, walk and cross our legs. It encourages feminine movement and comportment.

In other words, we do not merely wear the skirt. We experience it.

Wearing the Dream

Many crossdressers first became fascinated with feminine fashion when skirts were shorter and women dressed more formally than they often do today. The styles that captured our imaginations during adolescence can remain powerful decades later.

When we finally have the confidence, privacy or opportunity to dress as we always wished, we may choose the clothes of that long-held dream: a pretty minidress, sheer hosiery and high heels. We are not necessarily trying to dress like the average woman at the supermarket. Sometimes we are dressing like the woman we imagined becoming.

That also explains why some older crossdressers resist the command to “dress your age.” If someone spent much of her life unable to wear the fashions she loved, she may not be eager to skip directly to the sensible-shoes department. There is an element of making up for lost time and enjoying every inch of it.

A Little Glamour and a Lot of Confidence

A short dress can make an ordinary outing feel special. Add flattering hosiery, a pair of heels, jewelry and a handbag, and the result may feel polished, glamorous and wonderfully complete.

Naturally, the appropriate hemline depends on where we are going. The dress that works beautifully at a party may be too short for the office, church or a quiet afternoon at the mall. Being feminine also means understanding the occasion. A confident femulator chooses her hemline instead of letting her hemline choose the kind of attention she receives.

Still, there is nothing wrong with enjoying a little attention. A sincere compliment can reassure us that the image in the mirror is not wishful thinking. When someone says, “You have beautiful legs,” it validates the care we put into our presentation and may give us the courage to venture out again.

The Right to Choose

Women have spent generations expanding their clothing choices. They may wear trousers, long skirts, short skirts or no skirt at all. Crossdressers should permit themselves the same freedom.

Some of us feel most feminine in a knee-length pencil skirt. Others prefer a flowing midi dress. And some feel their best in a hemline that is short, perhaps even scandalously short (“Stana Short”). None is inherently more authentic than another. Personal style should reflect our figure, destination, comfort and personality, not an arbitrary rule about what a crossdresser is supposed to wear.

So why do crossdressers like short dresses and skirts? Because they are feminine. Because they feel different. Because they recall fashions we have admired for years. Because they add glamour and encourage feminine movement. And, yes, because some of us have great legs and enjoy showing them.

That is reason enough for me.

How about you? Do you prefer your hemlines short, conservative or somewhere in between—and what influences your choice?

Wearing Elágia

David Shawn Michaels and Gary Busey femulating in the 1998 film Rough Draft.

Learning to Wait in a Skirt

During the Summer of Love, I was sixteen and endlessly raiding my mother’s and sister’s wardrobes whenever I had the house to myself. Always alert to the possibility that someone might walk through the door at any moment, I worked quickly: dress, makeup, a few stolen poses in the mirror—then everything undone just as fast.

I was as confused as a teenager could be, but I knew one thing for certain: I liked dressing up. I liked making up. I liked becoming a young woman, even if only for a few fleeting minutes. I treasured that secret girl-time alone, though I had no idea where it might eventually lead.

Then one day, I thought I’d found an answer.

It was in the August 11, 1967, issue of Life magazine. Buried in the news section was a short article titled “Now the Mini Has a Man in It.” According to the piece, “In a ‘spontaneous’ fashion happening, miniskirts for men have begun showing up in Paris, Munich, London, and Tokyo.” Accompanying the article were photographs of miniskirted men in Europe and Japan (see image above).

I was stunned and thrilled. Naively, I assumed the fad would spread. Surely it wouldn’t be long before boys in the United States would be wearing miniskirts too. And when that happened, I could finally step outside in the skirts and dresses I loved, in plain sight.

It didn’t happen.

I waited patiently, but the fad never caught on. Still, in time, I did go public wearing the skirts and dresses I loved, just the same.

C’est la vie.

Wearing L'Agence

Robert Woolsey and Bert Wheeler femulating in the 1933 film So This Is Africa.

Dressing Daddy

I mentioned that my daughter gave me a Kate Spade handbag — an early Christmas gift to wear to my former company’s Christmas luncheon.

Christmas morning, she gave me three pairs of jeans. When I finally put on a pair last week, I realized that they were woman’s jeans.

Now that she is preparing to move to an apartment, she is going through her stuff to decide what to take, what to discard and what to give away. As a result, she gave me two Coach handbags, two Jessica Simpson handbags, a Victoria Secret makeup bag and a black pleated mini skirt.

Maybe now would be a good time to ask her to show me how to apply liquid eyeliner. She is very good at it; me, not so much.

Wearing Boston Proper (Source: Boston Proper)

Professional femulator Vicki St. James recounts "My First Time: Getting Caught in a Dress."