Halloween En Femme: The Good and the Bad

For many crossdressers, Halloween is the unofficial national holiday of crossdressing. It is the one day of the year when a man can wear a dress, heels, makeup and a wig in public without offering much of an explanation.

That makes a Halloween party an inviting place for a first public appearance en femme. However, Halloween has both advantages and disadvantages for the would-be femulator.

The Good

The greatest advantage is the ready-made excuse. If someone asks why you are dressed as a woman, the answer is obvious: “It’s Halloween.”

That excuse can provide enough courage to get a closeted crossdresser out the door for the first time. You can walk into a party wearing the outfit you have dreamed about wearing in public while telling yourself (and everyone else) that it is only a costume.

Halloween parties are also usually relaxed occasions. People expect unusual clothing, exaggerated makeup and characters who do not look the way they normally look. If your wig slips, your voice falters or you walk awkwardly in your heels, nobody is likely to care. Imperfection is part of the fun.

You may also discover that people react much more positively than you expected. Women may compliment your dress, makeup or legs. They may ask where you bought your shoes or offer to adjust your hair. Men may hold doors, offer you a seat or treat you differently simply because of the way you are presenting yourself.

For someone making a first appearance en femme, those little moments can be thrilling and educational. They may demonstrate that the fears keeping you in the closet were greater than the actual risks outside it.

Halloween also offers an opportunity to test your presentation. You can learn whether your shoes remain comfortable after several hours, whether your makeup survives a warm and crowded room and whether your outfit allows you to sit, walk and socialize gracefully.

Best of all, Halloween may provide your first taste of being accepted as a woman in a public setting. That experience can supply the confidence needed to venture out again when there is no Halloween costume to hide behind.

The Bad

The same costume excuse that makes Halloween comfortable can also work against you.

If you make too much of an effort, friends may wonder how you became so skilled at applying makeup, walking in heels and putting together a coordinated outfit. A borrowed dress, crooked wig and hairy legs suggest a joke. A perfectly fitted dress, polished nails, pierced ears and practiced feminine mannerisms may suggest that this is not your first rodeo.

You may receive questions such as, “Where did you learn to do your makeup?” or “How did you know your dress size?” Be prepared with answers or be prepared to smile mysteriously.

Another disadvantage is that some people assume a man dressed as a woman must be performing comedy. They may expect exaggerated gestures, a falsetto voice or behavior copied from a bad drag routine. If your goal is to present as an ordinary woman, being treated as the evening’s joke can be disappointing.

Alcohol can make matters worse. Someone who begins the evening with harmless teasing may become louder, more intrusive or less respectful after several drinks. A party guest may touch your wig, tug at your clothing or ask personal questions that would never be asked of a woman.

Photographs are another consideration. At a Halloween party, everyone has a phone, and party pictures can quickly appear online. Before attending, decide whether you are comfortable being photographed en femme and whether those pictures might be seen by relatives, neighbors or coworkers who do not know about your crossdressing.

There is also the temptation to overdo everything. Because it is Halloween, a crossdresser may choose the shortest skirt, highest heels, largest breasts and heaviest makeup available. That can be fun if an outrageous costume is the objective, but it does not teach much about presenting as a woman in everyday life.

Finally, the end of the evening can be bittersweet. After several happy hours en femme, removing the makeup and returning to male clothing may feel more difficult than expected. Halloween can open a door that you may not be eager to close again.

Making It a Treat

If you plan to attend a Halloween party en femme, decide beforehand what you want from the experience. Do you want to create an amusing costume, make a glamorous entrance or find out how it feels to socialize as a woman?

Dress for that goal, but also dress appropriately for the party. Wear shoes you can walk in, clothing you can sit in and makeup that will last. Arrange safe transportation, limit your alcohol and think twice before consenting to photographs.

Most importantly, enjoy yourself.

Halloween offers something rare: permission to try a different presentation without making a public declaration about who you are. For many crossdressers, it is the first step from the safety of the closet into the civilian population.

The Halloween excuse may get you through the door, but the confidence you gain can remain long after the jack-o’-lanterns have disappeared.

And if everyone tells you that you make a very convincing woman, just smile and say, “Beginner’s luck.”

Wearing Ann Taylor

Nick Kroll