CDSL: Cross Dressing as a Second Language

There are a small number of people in the world who simply never put a foot wrong or wander off-key in matters of appearance, and you may have met one or two in your life. My 8th grade English teacher was one such person. A polished platinum sophisticate, and a woman of means, to use the old fashioned expression, she drove the vintage Corvette or the snazzy Bricklin when the weather was fine, and a stately Jaguar saloon when it wasn’t. She wore a different dress every day, reputedly shipped home by the container load from upmarket Parisian salons after her twice yearly shopping pilgrimages.

She was a superb and dedicated teacher, but even if she had been inept, I don’t suspect that anyone in the administration could have taken her to task. Mrs. H. appeared always to be perfect, never a wrinkle, an errant thread or a bead of sweat. Hard to argue with that sort of competency. It is a rare gift.

I never had that gift. I did however have enough self-consciousness and insecurity in my teen years to put real thought into what cloths said about me. I funded my college education in part by selling clothes in retail settings. This formal and paid education stood me in good stead in my later professional life, in an era when we wore suits, and wearing them well did actually open doors.

My hard won talent for dapper is a bit of a relic now, a social appendix in our khaki-ocratic era of office casual, but the reflexes are still put to good use. I know what to buy, where to find it, how to put a value on it, and where to wear it. Getting ready for the day, or for a night in guy-mode is a simple exercise, and I never feel like I have it wrong.

It is different for the Cross Dresser is it not? The woman’s wardrobe is not the wardrobe of my birth and formative years. When I dress en femme, all the reflexive ease of the day-to-day routine is gone, and nothing comes “thoughtlessly”. As such, being dressed requires a laborious sort of translation. It feels like the same sort of process I go attempting to form sentences in French. Verb forms, sentence structure, subject/object relationships, etc, all assembled awkwardly under the ticking stopwatch of social acceptability. This is similar I imagine to what people speaking in an acquired language go through every day, with every utterance. What the ESL speaker loses in translation sometimes simply sounds adorable, but here and there, something gets so fully mangled that everyone is left dumbfounded. So it is with the CDSL student.

The translations start in the shops, online and real world. Assortments are bigger by a factor of 10. Sizes mystify, sleeve and skirt lengths confound, colors dazzle and seasons are sensitive. Prices run from the unjustifiably high to the criminally low.

On the odd chance that I find something I like, don’t already own, and can afford, and is on the racks in my size range, I am now looking at a 1 in 5 shot of it fitting well and looking good. Assume for a moment that it does fit and look well, we are still not quite there yet. I probably don’t have the right coat for a skirt of that length, or the coat I do have is too dressy for the rest of the ensemble. Oh, yeah, the rest of the ensemble, not quite so easily assembled is it? The blouse, is this the right neckline for the look? the right fabric for the season? a good shade for my complexion? Repeat the process. Accessories? Shoes, same again, and then, what about the bag?

After all of this, the Cross Dresser still earnestly scrambling up the learning curve discovers that women are held to a much higher standards of setting and age appropriateness than men are. This has a real limiting impact on those few outfits that we do get right. This looks great, but too much leg for daylight. Love that, but you can’t wear it shopping because it will rip your wig off in the fitting room. The sandals look and feel great but dammit its close to freezing and far from April. Make up, am I going to be seen under fluorescent lights or through candlelight? Jewelry? If Ithe piece looks and feels right, the likelihood is that I cannot find and operate the clasp. It is all a little dizzying.

Social commentator Malcolm Gladwell refers to a concept he calls the 10,000 Hour Rule in his recent book Outliers. Here is a grotesque reduction of the concept: do anything for 10,000 hours and you will be good at it, perhaps great. If the Beatles did not play 8 hours a night in Hamburg in their formative years, they would not have had a chance to get good enough to have given us Rubber Soul or Abbey Road (ed. hey, youngish readers …, it is true that your parents may have been insane, but in matters of music they do know more than you).

10,000 hours of Cross Dressing is not in my future, unless I become one of those Cryogenic cranks and am reanimated a century or two down the road in a liberal-minded and fashion obsessed society where my money still has value. And so I am consigned, like many, to putting the wrong foot forward and hitting off key notes along the way. It is a reality that the woman’s wardrobe will remain a Second Language for me.

This is not all bad, and I do want to underline one of the really good things that goes along with this reality. Cross Dressing, as comforting as it is, takes me out of my comfort zone. Getting out of the comfort zone helps me connect with that younger person within, the younger person who spent more time out of the zone than in. Not quite so young a person as the kid with the epic yearnings for Mrs. H, but a younger person than my age indicates. I enjoy that perspective. How about you?

Happy Valentines Day to you, and to those that love you.

(image credit: www.anntaylor.com)