(Cross) Dressing Your Age

Personally, I think that my legs are ok, but other people have convinced me that they are more so. My mother often said I had beautiful legs (and that “you should have been a girl with legs like yours”). My wife and other cisgender women have admitted that I have nicer legs than they do. 

I am tall, so my legs are long; maybe their length causes an optical illusion making them look better than they really are. I don't know, but I am not going to argue with success. If other people are happy with my legs, then I am happy with them, too.

So, I ask myself, “Since my legs are such a great asset, why not show them off?” I usually respond by wearing skirts and dresses with short hemlines (sometimes scandalously short hemlines) and high heels that are 2, 3 or 4 inches high.

When I add 4-inch heels to my 5-foot, 14-inch stature, I standout in a crowd topping out at an Amazonian 6 and 1/2 feet! So, when I am out in that crowd, some people may think I am an Amazon or I played for the WNBA; other people may think I am a man in drag.

One rule of thumb for passing is that you should crossdress your age, i.e., if you are an XX-year-old crossdresser, you should dress like an XX-year-old cisgender woman. At my age that means long skirts and lower heels or worse. By “worse” I am referring to the fact that these days cisgender women my age dress like cisgender men! Trousers, slacks and flats, not skirts, dresses and heels, is the norm especially among women my age.

I remember dining with four other T-girls in downtown Hartford. The place was full of 20- and 30-somethings, men and women alike. Do you know how many people I saw in the restaurant wearing a skirt or a dress? Two: one of the T-girls I was dining with and me! I did not see one cisgender woman in a skirt or dress.

To blend in that night, I should have worn slacks, not the short black skirt that I wore. And if I really wanted to pass that night, I should have worn flats instead of high-heeled boots, socks instead of pantyhose, a plaid shirt instead of an animal-print top, boxers instead of a panty girdle, a t-shirt instead of a bra. Also, I should have nixed the makeup and left my pocketbook, wig, and jewelry at home. Then, I would have passed easily, but as a man.

In my opinion, passing is overrated. If I have to make a choice between dressing to pass or dressing to thrill, I will choose dressing to thrill every time. Sometimes, I dress to pass, but that's no fun. For starters, when I dress to pass, I usually am not that happy with the clothing I wear. To make matters worse, when I dress to pass, I constantly worry about passing. I cannot enjoy myself out en femme. It is a real drag!

On the other hand, when I dress to thrill, I am very happy with the way I look and I can be myself because I do not worry about passing. What is interesting is that sometimes when I am dressed to thrill, I pass!

Here is one of my favorite passing-when-I-wasn't-trying stories.

Doing outreach at Southern Connecticut State University, I started the day in 3-1/2-inch stilettos, but just in case, I brought a pair of flats that I left in the car. After shopping at the mall before outreach and going to the first of two classes to do outreach, my 3-1/2-inch stilettos had to go, so I went to the car to fetch my more comfortable shoes.

As I walked through the parking lot, I saw a university dump truck parked right in front of the car. The driver was talking with another university employee standing next to the truck. Oh, damn, just what I needed, the classic transwoman nightmare, a Transwoman vs. Macho Guy Face-Off!

I was ready for the worst! Making a beeline for the car, I tried to ignore the guys, but the guy standing by the side of the truck greeted me with a very flirtatious, “Good afternoon,” while the guy in the truck smiled appreciatively and drove away.

They flirted with me! Wow – that was so unexpected!

So when I go out en femme, I am likely to dress to thrill and show off my legs rather than dress to pass. And if I do pass, then that is just an extra thrill.

Wearing Bebe

Eve, a lady in red