Dressing Your Age

Stana, who--like me--is in her late middle-age, discusses whether dressing to match your age is worth it.

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.

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.

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!