David Thomas’s transgender diary

‘I was all sorted for the funeral. There was just one problem. What on earth was I going to wear?’

BLANK! BLANK! BLANKETY-BLANK! If you recall the opening of Four Weddings and a Funeral, you won’t need me to fill in those blanks. Suffice it to say, I was channelling my inner Hugh Grant, driving down a dual carriageway, hopelessly late for a church service.

The occasion was a funeral – the mother of one of my oldest friends – rather than a wedding. Like Hugh, I was frantically looking for the right exit. I didn’t actually reverse back down the highway to take it, as he did. But I did make a pretty dramatic, last-second swerve from the fast lane to the slip road.

I swear I’d tried to be on time. I’d really tried. I’d familiarised myself with the route from Sussex to Somerset. I’d allowed for delays. I was all sorted.

There was just one problem. What on earth was I going to wear?

When I was a normal(ish) bloke, events like this were a doddle. Men’s clothes are mostly just uniforms. For funerals that means a more formal twist on the Blues Brothers/reservoir Dogs look: black suit, shoes and tie, white shirt, usually best to forget the black shades.

In this case, however, the dress code was, ‘No black.’ It was an occasion to celebrate a life, as much as to mourn its passing. Again, as a man, that was perfectly achievable. I have an elegant, silvery grey Gieves & Hawkes suit. Add a pale-blue shirt and an elegantly colourful tie and… bingo! Job done.

The trouble is, I can’t wear those clothes any more. Partly, I just don’t want to. But also, they hang all wrong on me. For some reason, every suit I own is about four inches too wide at the shoulders and the trousers fall off without drastic belt-tightening. OK, I’ve lost a bit of weight, but not that much. And no amount of oestrogen shrinks one’s skeleton. I think I must have been deluded about my actual proportions.

So much for men’s clothes, what about women’s? Now, I went a bit crazy when I began the transition process, making up for 40 years of lost shopping. I would have had no trouble in finding a chic, appropriate dress or little skirt-suit. I’d have spent ages getting it right. But I’d have got there.

Trouble is, I’m still stuck in the no-man-or-woman’s land of transition. I can’t get away with wearing frocks yet. I needed a workable compromise.

Cue hours of emptying wardrobes and drawers, trying things on, throwing them off and scrabbling for something else. I did this on the night before the funeral, by the way. I was thinking ahead.

I came up with a compromise: white Calvin Klein men’s jeans; a vintage Scott Crolla men’s jacket in dark blue shot silk; a pale-pink silk vest and voile shirt from Me+em; and dark-blue suede ankle boots. It may sound mad, but it looked great.

Come the big day, I was ready in plenty of time. I went downstairs, got in the car… then stopped. No, it wouldn’t do. The vest and shirt were lovely, but they were too showy, too femme, too, ‘Look at me, I’m a tranny!’

I got out of the car, dashed back to the house, up three flights of stairs to my flat, beginning to get sweaty a bit too early in the day, and raced into my bedroom.

After frantic clothes-hunting, I spotted a blue-and-white striped silk shirt from Pure. Excellent, matchy-matchy, genderneutral option! Pure is discreetly middleclass and middle-aged. Who could object?

I put on the shirt, dashed back to the car, drove off. Three miles down the road I realised that I was no longer wearing my jacket. Cue a sudden U-turn, a frantic hurtle back home, another run up the stairs, more sweat, more swearing. Finally, I was underway. But now all my spare time had gone.

Somehow, I reached the church with seconds to spare. The setting was idyllic, the weather gorgeous. Only problem: the nearest parking space was 400 yards away. I ran up the lane and arrived, panting and now molten, to be greeted by my friend, who bore the wry grin of a man not surprised by the turn of events.

‘The church is packed,’ he said. ‘You’ll have to take a family seat at the front.’

I walked down the aisle, throwing embarrassed grins at all the punctual people whose inferior pews I was passing, and collapsed alongside the deceased lady’s brother, who’d been my very first boss, years ago. It was that kind of event.

Afterwards, as everyone milled around the aisle, I saw my friend’s ex-wife coming towards me looking wonderful. I pointed at her beautiful silk dress and gave her the thumbs-up. When we finally made contact, I said, ‘I’m sorry I was so late. Total wardrobe malfunction.’

She looked at me with an affectionate smile and said, ‘Yes, I’d been wondering what you were going to wear.’

Author David Thomas still lives as a man, but has begun the male-to-female gender transition that will eventually result in becoming a woman. Each week he chronicles his progress