David Thomas’s transgender diary

For the past five years I have been on a personal mission to save the British retail sector from total collapse. Entire high streets and online fashion sites only remain in business thanks to my crazed determination to make up for a lifetime of missed shopping opportunities. In fact, the only thing I’ve spent more on than retail therapy is, er… therapy.

Tragically, however, The Micawber Principle has started to take effect, as in, ‘Annual income twenty pounds, annual expenditure twenty pounds ought and six, result misery.’ Or in my case, a very large overdraft.

I have therefore had to discipline myself and stop buying absolutely anything I could ever possibly want, in favour of things I actually, definitely need. Such as, for example, a pair of sensible, lace-up leather boots, with soles sturdy enough to keep my feet warm and dry when pavements are cold and wet.

In years gone by, this problem was easily solved. I went to the local cobblers and asked them to put a new set of soles on my nice, dark-brown suede boots, which I bought about 15 years ago. And I am now so old that I think of that as being quite recently.

Failing that, I could walk into any major high-street shoe shop, say, ‘I’d like a new pair of boots please, size 11,’ and the assistant would say, ‘Certainly, sir, come this way,’ before providing me with a wide selection of suitable styles.

Now, though, two things have changed. First, I have discovered that I am actually a size 10 and have spent the past 40 years wearing shoes that were exceedingly comfortable because they were at least a size too big and cushioned by thick, fluffy socks. Secondly, I am now looking for women’s winter boots and suddenly, size matters… and for completely the opposite reason than before. Big is definitely not better. Before going any further, let it be said that whopping plates of meat are no impediment to beauty. Elle Macpherson, Tyra Banks and Uma Thurman all have big feet. And even that lovely, elfin, deliciously feminine screen goddess Audrey Hepburn was only a half-size smaller than me. But you try telling most shoe manufacturers that.

Anyway, micro-rant over… I get most of my footwear from Long Tall Sally, which is getting better and better at seeing what’s fashionable and immediately reproducing it in giraffe sizes. But it doesn’t seem to have precisely what I want this winter.

So, I trawled the internet and finally came upon one brand offering a wide range of sturdy, weatherproof boots in sizes that go beyond even my requirements. And the name of that brand? Dr Martens.

Now, I was never a Doc Martens geezer, and I wouldn’t have thought of myself as a DMS gal, either. They’re all urban, alternative and roughedged, and I am, to be honest, more of a conventional, Home Counties soul, at heart. Also, when I looked at their sizes, they had boots that were 9½ and 10½, but no basic 10 in the middle. I mail-ordered them in black: both sizes, just to be on the safe side.

The 10½s were incredibly comfy, but so big they looked like clown shoes. The 9½s were visibly smaller, both in length and width, and fitted perfectly, except that my big toes were touching the front of the boots.

Obviously, I wanted the smaller size. But would they be unwearable? I went online, and found entire threads debating the proposition that Doc Martens had to be bought small, because the leather softened and stretched, and a few weeks of pain and bleeding were all just part of the whole experience.

Even so, they did seem a little chunky, so I consulted my sister Clare, who’s very arty, eco-conscious and boot-wearing. Naturally, she drooled over my lovely pristine DMS. ‘They look really small!’ she exclaimed, before I had even raised the issue.

Then I asked my Swiss friend, Ursula, who was staying with me. ‘Be honest, do these make my feet look enormous?’ She cooed, ‘No, darling, they’re really cute and sexy.’

By then I was 99 per cent convinced, and the clincher came when I saw a picture of a model in a magazine wearing a Toast dress and laceup boots; I adore Toast, and her feet looked at least as long as mine.

So that did it. I have my Doc Martens. And if you don’t like them, well, these boots are just gonna walk all over you.

I am now looking for women’s winter boots and suddenly size matters… and for completely the opposite reason than before