David Thomas’s trans­gen­der di­ary

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‘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

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