How to Look Like a Crossdresser

Most crossdressers want to be perceived as women—not as men wearing women’s clothing. Yet some unknowingly make presentation choices that announce their crossdressing before they ever say a word.

The problem usually is not a masculine face, broad shoulders, height or any other physical characteristic that cannot easily be changed. Women come in every conceivable size and shape. What attracts unwanted attention is often a collection of avoidable mistakes.

Hair is one of the biggest giveaways—especially hair in all the wrong places. Hairy arms, legs, hands, chests and backs do not work well with sleeveless tops, low necklines, short skirts or open-back dresses. Neither does a visible beard beneath heavy makeup. A close shave, color corrector and carefully applied foundation can help, but piling on more foundation usually creates a mask without concealing the beard.

Eyebrows matter, too. Untamed masculine eyebrows beneath an otherwise carefully made-up face can spoil the whole presentation. They need not be plucked into dramatically feminine arches, but trimming and shaping them can make an enormous difference.

Then there is the wig.

A cheap, shiny wig that looks as though it came from a Halloween costume shop is difficult to overlook. So is a wig that sits too high, too low or crooked on the head. Extremely long hair can also look out of place on someone whose face and wardrobe suggest a more mature woman. A good-quality wig in a believable color and age-appropriate style is one of the best investments a crossdresser can make.

Breast forms create another temptation. Some crossdressers believe bigger is always better. It is not. Huge breasts on a body that cannot realistically support them look artificial and throw the entire figure out of proportion. The same is true of badly positioned hip and rear padding. Padding should create a subtle feminine silhouette, not make it appear that sofa cushions have been stuffed under a dress.

Makeup presents similar dangers. The objective should be to enhance the face, not repaint it. Heavy eyeliner, enormous false eyelashes, brilliant eye shadow, overdrawn lips and bright circles of blush may look dramatic in the mirror, but they seldom look natural in daylight. Makeup that photographs well under dim indoor lighting can look startling in a supermarket at noon.

Clothing may be the biggest giveaway of all.

Fetishwear, extreme heels, microscopic skirts, plunging necklines and skin-tight dresses attract attention regardless of who is wearing them. When combined, they create a caricature of femininity. Dressing like a stereotypical streetwalker is unlikely to help anyone blend in at the mall, grocery store or family restaurant.

Dressing too young causes the same problem. There is nothing wrong with looking youthful, but clothes designed for a 19-year-old seldom make a 60-year-old look 19. More often, they make the wearer look like a 60-year-old dressed as a teenager. Stylish, flattering and age-appropriate clothing is much more convincing—and usually more attractive.

The occasion matters as much as age. A cocktail dress, sparkling jewelry and four-inch pumps may be perfect for a party, but they look conspicuous while buying milk on Tuesday morning. Before going out, look at what women of a similar age are wearing at the destination. You do not have to copy them exactly, but they provide a useful reality check.

Poorly fitted clothes are another common mistake. A dress that pulls across the shoulders, a skirt that twists around the waist, a blouse whose buttons strain or a bra that rides halfway up the back will not create a polished appearance. The number printed on the label is irrelevant. Fit is everything.

Even a convincing appearance can be undermined by movement. Taking enormous strides in high heels, sitting with the knees far apart, constantly adjusting one’s clothes, swinging a handbag like a toolbox or nervously looking around to see who is watching can draw more attention than a masculine facial feature ever will.

The goal is not perfection. Few women look perfect, and trying too hard can be a giveaway in itself. The goal is a believable, coordinated presentation appropriate for one’s age, figure, destination and time of day.

Study women rather than fantasies about women. Notice their hair, makeup, proportions, clothes, posture and movements. Practice at home. Take photographs. Examine them honestly. Correct one problem at a time.

Good crossdressing is hard work, but I love my job.

Wearing JustFab

Frederick Weller femulating on television's In Plain Sight (2010).