Monday, October 19, 2020

(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
Wearing Bebe

Eve, a lady in red
Eve, a lady in red


  1. Well,
    1. women dress UP when they're going to a special event.
    2. anytime Meg is out is a special event.
    Therefore, Meg always dresses UP.

  2. Sally StoneOctober 19, 2020

    Stana, I'm so glad you wrote this article. It matches exactly, the way I feel about passing. I'm never trashy or inappropriate in the way I dress, but I do prefer shorter hemlines. And in my humble opinion, life is too short to waste an outing wearing pants. Ultimately, I dress to please myself, not to ensure I am going to pass. Thanks so much for an insightful article.

  3. If you can 'look the part' (and you. do!), live the part.
    Ladies have guess timated my age as 46!
    A total rush @ age. 66.75!
    My face is wrinkle free, in spite of working outside for 30+ years. Also credit Maybelline...

  4. Agreed, on many levels. One reason I cross dress is to feel feminine. And I have to wear pants in Guy mode, so why wear them in Gal mode? This becomes tricky only when getting together with my cis gender girl friends for coffee or whatever. I want to be in a skirt, they want to be in pants (yoga or jeans, usually). So the choice is do I also put on leggings and sneakers and fit in, or do I get out my jean skirt and comfy wedge heels and risk standing out? One time I was going for walk with one gal and showed up at her house in a skort and sandals. She was dressed for a run (leggings, sneakers and hoodie), but she looked at me and changed into jeans and nice top. We have actually talked about my fashion choices and (more importantly) the WHY behind my choices. As a result, I usually go with standing out - and they are becoming OK with that. Because that's what friends do.

  5. I know from the day we met in Dayton years ago, you have amazing legs and should show them off! To hell with age!
    I have somewhat the same problem with my hair which is almost down to the middle of my back...very unusual for a woman of my age. But I love it none the less.

  6. I live by the tennant "When I Rome, dress like the Romans". If I go to the grocery store, I will wear either casual Saturday clothing, or something a bit more "office" attire, like I'm stopping to shop after a hard day selling clothing at Macy's. My wife sold shoes in a Mall, a CD would routinely come in shopping in
    flowing gowns, big floppy 70's flower power hat, and pretty much anything a woman wouldn't wear to the mall to buy shoes. I like to be low-key and blend in. But to each their own to meet their level of goal satisfaction.

    Barbara Ann

  7. Bear in mind, too, a woman often dresses to accentuate her best feature... if that is your legs, you could reasonably raise your hemline an inch or two, and wear more skirts...

  8. I have to agree with Meg, since transitioning a few years back I find I am wearing dresses and skirt less often, like heels these are garments for special occasions. When I have reason to dress up (even if it's just lunch with some girl friends) I will, and maybe give my legs an airing, but most of the time these days it's jeans and a sweater.