The clothes have been hanging in my wardrobe for weeks. Navy pinstripe pencil skirt. Burgundy faux leather pencil skirt. Black jeggings. White camisole. Block heels. Trainers. A 44A bra that actually fits.
Sunday is the day. Café with a friend who knows. My first time out in feminine clothing as myself.
And I cannot decide what to wear.
Skirt or Jeggings?
This was the first fork in the road. The jeggings feel safer—they're feminine, yes, but from a distance they could pass as slim-fit men's trousers. Nobody would look twice. I could ease into this.
But that's exactly why I ruled them out.
I've spent thirty years easing into things. Thirty years of "maybe next time" and "somewhere less public" and "something less obvious." The jeggings feel like another compromise. Another way of hiding while pretending I'm not.
The skirt is unmistakable. A man in a skirt is making a choice that can't be explained away. That's terrifying. That's also the point.
Navy pinstripe won over burgundy faux leather. More understated. Office-appropriate, even. The kind of skirt that says "I dress like this" rather than "I'm making a statement."
Heels or Trainers?
I own block heels in black and nude. I also own trainers that would work with either outfit. The practical argument for trainers is obvious: comfort, stability, the ability to walk away quickly if things go wrong.
But there's something about heels.
When I put them on at home—door locked, curtains drawn—something shifts. My posture changes. I stand differently. I feel like the version of myself I've been hiding for three decades.
The block heels aren't stilettos. They're stable, walkable, professional. Three inches that change everything about how I carry myself.
I'm wearing the heels.
The Question I Didn't Expect
Bra or no bra?
I have pecs, not breasts. A 44A fits because of my chest measurement, not because I'm filling the cups. So why would I wear one?
I've thought about this more than I expected to. The camisole has a lace trim that sits better with something underneath. The straps show at certain angles—intentionally, I think, the way women's tops are designed. Without a bra, it looks like I forgot something. With one, the whole outfit coheres.
There's also something about the completeness of it. The outfit isn't a costume if every layer is intentional. The bra isn't about creating shape I don't have. It's about wearing feminine clothes as they're meant to be worn.
I'm still deciding. I have until Sunday.
What This Is Really About
None of these decisions are really about fabric or heel height or underwire. They're about how visible I'm willing to be. How much of myself I'm ready to stop hiding.
The safe choice exists for every question: jeggings, trainers, skip the bra. Nobody would blame me. Most people wouldn't even notice.
But I've been making safe choices for thirty years. They haven't made me happy. They've just made me invisible.
Sunday, I'm choosing to be seen.
Navy pinstripe pencil skirt. White lace-trim camisole. Black bomber jacket. Block heels. And probably—almost certainly—the bra.
I'll let you know how it goes.