I tried something different on New Year’s Eve. I dressed as a bloke. I didn’t actually beard up or pad my pants with socks or anything, but I took what I thought would be the easy way out of a black tie soirée. I don’t mean I shinned down the drainpipe when the canapés ran low. I mean I opted for a low stress option. I took it literally. I wore a black tie. And a man’s white shirt.

That afternoon I had been on a charity shop spree with the girls, and when I joked that I was tempted to go as a bloke to save the anxious lady trussing, they said “why don’t you then?”

Charity shops are the right places to take your friends up on a sartorial challenge. Need a man’s white shirt that doesn’t gape at the boobs and a thin black tie for a 10-12 year old boy? Look no further than this potluck bin, madam.

Thus was it decided. No dress for me. No laddering of tights, no rotating strapless bra. A white shirt and a bar mitzvah tie. I didn’t even wash the shirt. I got it home and when I realised it smelled clean and not of geriatric puke, I just whacked it on.

Initially I whacked it on with a skirt and tights, thinking I looked a bit preppy, like a prefect with a hipflask. But when Matt’s eyes popped out of his head and he said, between fondles, that it might be a bit ‘risqué’ for company, I got a bit huffy about outdated saucy connotations ruining everything for us non-prostitutes. So I put some black trousers on and thought I’d feel better.

But I didn’t. I felt like a nob. I felt like I had tried even harder in not ‘trying’, even sluttier than if I’d worn the slurpy dress that once popped a nip out as I suckled at a vodka luge. I was cross that my solution hadn’t solved the problem. Cross that I should feel just as uncomfortable in a dead man’s shirt with a ripped elbow with no bits, no obvious femininity, no ‘effort’ on display.

The little bell in the feminist ward of my brain rang out: “Oi. Dipstick. It’s because you’re not supposed to wear the timeless power garb of men – you’re supposed to be sculpted in a dress pleasing to the eye and hurtful to the waist.” I shushed the little bell. I didn’t have time for feminism; I was running late and Matt had got ready in a man-typical five minutes and was casually strumming his guitar while I stood, hating myself.

Then I realised something. There is something about any kind of ‘proper dressing up’ that always makes me feel naked. In both expensive dresses and cheap dresses comes the same awkwardness. In revealing dresses or modest dresses, a similar feeling of exposure. In costumes for telly or plays, always a strange displacement. The fact is most sane people feel a little daunted when they think people might really be looking at them. Like, really looking. And in ‘dressing up’, you’re sort of inviting the society of glances, the culture of being watched. Which is a bit bonkers when you think about it.

I think, really, I mostly got cross with myself that, despite all my maturing and emboldening, I might still not be ready for the statement that is “I am bored of dresses and shall tonight be wearing the same as you, Big Bob McManfist.”

I wonder if it will always be that way or if I’m due an enlightening period in my late 30s of totally not giving a dog-doo. I hope so. I have a fancy for waistcoats and pocket-watches.