Thirty years. That's how long I've been buying, hiding, and purging. Three decades of secret Amazon orders, of clothes stuffed in the back of closets, of shame that never quite went away no matter how many times I threw everything out.
Yesterday, I wore a skirt to a café.
Not a costume. Not a dare. Just a navy pinstripe pencil skirt, a white lace-trim camisole, my black bomber jacket, and the quiet certainty that I was done hiding.
The Morning Of
I stood in front of my closet for twenty minutes. Not because I didn't know what to wear—I'd planned this outfit for weeks—but because my hands wouldn't stop shaking.
The skirt was nothing dramatic. Navy with subtle pinstripes, fitted, hits just above the knee. I'd paired it with a white camisole with delicate lace trim—feminine but not fussy. The bomber jacket over the top gave it that masculine-feminine contrast I was going for. Block heels completed it. Simple. Put-together. The kind of outfit that says "I meant to look like this."
My wife watched from the bed. "You look good," she said. And I believed her.
The Walk In
The café was busy. Saturday morning crowd, laptops and lattes, the comfortable hum of people minding their own business.
I'd chosen this place deliberately. Close enough to home that I could retreat if I needed to. Public enough that there would be witnesses if anything went wrong. My friend Sarah was already there, saving a table near the window.
I walked in.
And nothing happened.
No stares. No whispers. No dramatic record-scratch moment where everyone turned to look. Just a guy in a skirt ordering a flat white, same as anyone else.
What I Learned
The anxiety doesn't disappear—it just becomes background noise. By the time I finished my coffee, I'd almost forgotten what I was wearing. Almost.
There's a particular kind of freedom in finally doing the thing you've been afraid of for decades. Not the absence of fear, but the presence of something stronger. Call it defiance. Call it authenticity. Call it being too tired to pretend anymore.
I'm not here to make a statement or start a movement. I'm just a guy who likes wearing skirts, who spent thirty years pretending he didn't, and who finally decided that life is too short for that kind of hiding.
This is the first entry in what I'm calling The Hourglass Project. Building the body. Wearing the clothes. Living the life.
More to come.