Dressed to Thrill (Passing Optional)

I didn’t decide my legs were exceptional. Other people did that for me.

My mother was the first. She used to say I had beautiful legs and then, with a mix of admiration and regret, add, “You should have been a girl with legs like yours.” My wife has said the same more diplomatically. Other cisgender women have been less diplomatic, admitting outright that my legs are nicer than theirs.

At some point, you stop arguing with that kind of consensus.

I’m tall, so my legs are long. Maybe that length creates an optical illusion that elevates them beyond their actual merit. I honestly don’t know. What I do know is this: if people keep noticing, complimenting, and occasionally envying your legs, it would be foolish not to treat them like the asset they clearly are.

Which raises the obvious question: if you’ve got it, why hide it?

My answer has been skirts and dresses with short hemlines, sometimes unapologetically short (“Stana Short”) and heels ranging from two to four inches. Add four-inch heels to my six-foot frame and I don’t just enter a room; I announce myself. I top out at nearly six and a half feet, tall enough that strangers start inventing backstories. Some assume I’m an Amazon. Others think I played for the WNBA. A few decide I must be a man in drag.

They’re not entirely wrong but they’re missing the point.

There’s a well-worn rule in crossdressing circles: dress your age if you want to pass. If you’re an XX-year-old crossdresser, you should dress like an XX-year-old cisgender woman. At my age, that rule translates into longer skirts, lower heels or worse.

By “worse,” I mean this uncomfortable truth: many cisgender women my age now dress like cisgender men. Slacks, trousers, and flats dominate. Skirts, dresses, and heels have largely disappeared. Camouflage, masquerading as practicality.

I saw this vividly one night while dining with four other T-girls in downtown Hartford. The restaurant was packed with twenty- and thirty-somethings men and women. Want to guess how many people I saw wearing a skirt or dress? Two. One of the T-girls at our table and me. Not a single cisgender woman in the room was wearing one.

If I’d truly wanted to blend in, I should have worn slacks instead of the short black skirt I had on. And if I really wanted to pass, I should have committed fully: 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. Skip the makeup. Leave the wig, jewelry, and designer bag at home.

I would have passed effortlessly.

As a man.

That’s when I decided passing is wildly overrated.

If the choice is between dressing to pass and dressing to thrill, I’ll choose thrill every time. Dressing to pass is joyless. The clothes rarely make me happy, and the entire experience becomes an anxious audit: Do I pass? Did they clock me? What about now?

It’s exhausting. It drains all the pleasure out of being en femme.

When I dress to thrill, the opposite happens. I like what I see. I feel confident, expressive, alive. I’m not policing myself or monitoring strangers. I’m simply being me and here’s the delicious irony: that’s often when I pass anyway.

One of my favorite examples happened during outreach at Southern Connecticut State University. I started the day in three-and-a-half-inch stilettos but tossed a pair of flats into the car just in case. After shopping at the mall and visiting the first of two classes, the stilettos finally won. I headed back to the parking lot to change shoes.

That’s when I saw it: a university dump truck parked directly in front of my car. The driver was chatting with another university employee beside the truck.

Perfect. The classic nightmare scenario. Crossdresser versus Macho Guy, center stage.

Bracing myself, I made a beeline for the car and tried to disappear. Instead, the man standing beside the truck looked at me and said, warmly and unmistakably flirtatiously, “Good afternoon.” The driver smiled, lingered for a moment, and then drove off.

They flirted with me.

I wasn’t trying to pass. I was trying to get to my flats.

So now, when I go out en femme, I dress to thrill and show off my legs. If I pass, that’s fine. If I don’t, that’s fine too. Passing is optional.

Thrill is not.

Wearing Boston Proper

Wearing Boston Proper