I would go out tonight …

Anna at window

… but I haven’t got a stitch to wear! So croons Morrissey in The Smiths’ song ‘This charming man’, released in 1984. It was in that year, my first year at university, that I was introduced to The Smiths, and for some reason theirs were the first songs I’d really paid attention to for their lyrics. (I was also said to do a passable impression of Morrissey’s singing style.) But I don’t want to talk about the relationship between music and text, or about Smiths fandom, or even about Morrissey’s objectionable politics.

Back then, like many if not most people, I wore ’80s fashion. That is to say, I wore clothes that were on sale in high-street shops like River Island, Next and Top Man (no Top Shop for me, never mind Miss Selfridge or Dorothy Perkins). I tended to go for bright, garish clothes in various combinations, with little concession to what anyone else was wearing. My shoes were similarly colourful, as were my glasses and from time to time my hair (in a Limahl-style mullet, of course!).

I did give some thought to how I looked, and tried to coordinate my outfits to an extent, but I was still working with a palette of clothes that were effectively chosen for me. You see, not only was I shopping in a limited selection of clothing stores in a fairly small town, but my shopping expeditions – which I always found excruciating – were almost never solo outings. Confession time. Right into my twenties, I probably wouldn’t have bought new clothes if my mum hadn’t forced me into a shop. And when I married, at 30, I’m ashamed to say that I let my wife take on the role of my personal shopper.

Not only that, of course, but I considered myself restricted to so-called men’s clothing. You may have read that the ’80s were a time when gender boundaries were blurred and men were just as likely as women (or anyone else) to wear lots of makeup. Not in my experience. That may have been true for pop musicians and cultural icons, but not for ordinary people. Male contemporaries of mine in 1984 didn’t wear makeup and generally wore pretty drab clothing. More Morrissey than Boy George, anyway. We’d lived through the ’70s, after all.


The term cross-dressing is problematic. It presupposes a general conformity to gendered clothing stereotypes (and the existence of two and only two genders): without that background, there would be no clothing gender divide to cross. It is also one-directional (at least in ‘western’ culture): only men cross-dress, women being able to cross the presumed gender divide rather more freely these days (which is not to say that women can get away with wearing whatever they want, of course).

I’ve heard a few, mainly older, trans women say that before transitioning they used to ‘cross-dress’ on occasion as a way of exploring their gender identity. (I haven’t heard trans men speaking of a similar experience, probably because it’s far easier for a trans man to dress in male-coded clothing without outing himself as trans.) However, I would never use the term for my own explorations of gender identity.

Since cross-dressing only applies to men in our culture, I couldn’t cross-dress if I wanted to. As a woman, I could of course wear a suit and tie, but that wouldn’t be cross-dressing. A gender-non-conforming trans man, on the other hand, could presumably be considered to cross-dress if he wore a skirt. Indeed, most trans men were probably forced to cross-dress as children. (And if we allow cross-dressing to mean wearing female-coded clothing when not female, the same probably applies to many AFAB – assigned-female-at-birth – non-binary people.)

I’m not in the position of a trans man or AFAB non-binary person (and certainly can’t speak for them), but I can speak of my own experiences. I was made to wear exclusively male-coded clothing as a child, and societal expectations (together with my personal shoppers!) meant that I continued to do so long after I had the freedom, in principle, to do otherwise.

Gender explorations

Like most young children, I suspect, I played at dressing up, and I dare say there were times when I tried on clothing belonging to female relatives. But none of that jumps out at me from memories of early childhood. No, we need to move forward again to the ’80s, when as a teenager I desperately wanted to be like the other girls and would use any excuse to make tentative transitions into their world.

There were times when I was at school that I found myself in exclusively female company – usually when taking part in extracurricular musical activities, as for some reason there was a significant gender imbalance among players of wind instruments. On some of these occasions I borrowed items of clothing belonging to other girls, ‘for fun’, or allowed them to apply eye makeup to me, ‘for fun’. But inwardly I felt included.

In 1984, I took part in a student revue in which I played the role of an ‘absent-minded professor’ who gave a speech while stripping at the same time, thus revealing the lacy underwear he was wearing beneath his academic garb. I actually did the sketch twice, but the first time, I just stripped to a pair of ‘humorous’ Y-fronts. For the second show, I thought that borrowing another student’s bra and pants (?!) would make the sketch better. It probably did. But.

A few years later, in the course of my second degree, I asked my then girlfriend if she’d help me buy some women’s clothing for some kind of ‘cross-dressing’ party. (I don’t really know what kind of party it was, because I ended up not going.) She was happy to go to a second-hand clothes shop with me to help me find a slinky black dress, and she even helped me choose some women’s underwear, just so I could get into character a bit better. Just for fun.

I kept those clothes for a while, but didn’t ever wear them in public. Eventually, out of a sense of shame, I got rid of them. After all, the slinky black dress had just made me look like the hideous caricature of a man-in-a-dress that I’d been afraid of. Clearly this wasn’t for me. And I would soon be getting married too.

The wilderness years

I’m definitely not talking about my marriage as a whole, but in terms of self-expression through clothing and personal presentation, nothing much happened for a couple of decades. I allowed my style to be subtly shaped by my wife’s idea of how I should look, and shopped for new clothes reluctantly (though the advent of online shopping made things slightly easier).

Just before I started going out with my future wife, I went on holiday to Paris by myself. (There’s an element of freedom in that – you can do as much or as little as you want – but then there are some things you just need to share with someone.) Anyway, at one point I was looking at watches in a shop window – my old watch had broken – and I started crying because I realised that I really, really wanted to wear one of the women’s watches, but felt I would never be able to.

During my marriage, there were a few other times when I was similarly overcome with emotion when I saw a lovely piece of clothing or jewellery that simply wasn’t destined for me to wear. (But I did actually buy a pair of women’s trousers once, from a shop in Skye. I had a yearning for something bright and garish, and that meant I had to shop outside the men’s section. They didn’t fit terribly well, though, which made me think that perhaps my body was just the wrong shape.)

I was able to console myself, however. Throughout the years, I always had certain items of clothing that, to me, were secretly feminine. There was something about them that I could use to make me feel more comfortable about myself. For instance, I had a pair of lightweight trousers with zip-off legs and zips at the ankles, which made them prettily flared (though otherwise pretty ordinary-looking). For a long time, they were my favourite trousers because of that little detail that only I knew about.


As I’ve recounted before (Then was not the time), I went on a big family holiday just before I first told someone face-to-face that I was trans. The anticipation of doing that when I got back added an extra frisson of excitement to the whole holiday experience.

Family holidays for us usually involved a mixture of visiting museums and galleries, going for long adventurous walks, and shopping. There was always a little bit of shopping. I never really liked that bit.

This time, it was different.

I ‘dutifully’ followed my wife around a number of clothes shops on that holiday. Indeed, I positively encouraged her. And probably for the first time ever, as I hung back a little to avoid arousing suspicion, I took an interest in the clothes that I saw. I surreptitiously swung the odd hanger aside and felt the fabric between my fingers, taking in the universe of colours, patterns, textures and styles as I never had done before.

Returning to Edinburgh after three weeks away, I found myself at home alone quite a bit, and ended up trying on almost all my wife’s clothes (except her underwear!), just to get a feel for what might look OK on me. That also gave me a pretty good idea of my dress size. And when my wife found out (as she eventually did), I inherited one or two items of clothing that she didn’t wear any more. (In fact, I just inherited another dress from her today!)


Mirror selfie, new tunic
Self image

In early 2017 I started shopping for a new wardrobe in earnest. I bought some clothes online (and returned half of them!), but eventually plucked up the courage to try clothes on in shops. (At least I knew what sizes to try, but I was afraid of how people would react. As it happened, I needn’t have worried.)

Once I was over that initial hurdle, there was no stopping me! I would browse my favourite clothing websites regularly and could scarcely walk past a clothes shop without popping in to see if there was anything new inside. Somehow, my dread of clothes shopping had been transformed into delight.

Before long, I realised that I wasn’t going to get any more wear out of the androgynous-seeming clothes that I’d kept from my wilderness years: they carried too much emotional baggage, and simply weren’t in keeping with my new style. Besides, as a trans woman, I still don’t feel comfortable dressing too androgynously: I have a hard enough time being misgendered as it is. The more social cues to my gender, the better. Anyway, pretty much all my old clothes ended up in charity shops or went out for recycling.

So the clothes I wear today are more or less completely different from the clothes I wore two years ago. I still have some socks that I’ll wear occasionally – and I have had to buy ‘men’s’ socks since beginning my transition, simply because my feet are so grotesquely long. Sadly they aren’t available in the colours and patterns of smaller, ‘women’s’ socks. Shoes have been problematic too, but I have managed to find half a dozen pairs of shoes, boots, sandals and trainers that fit my long, narrow feet – after a great deal of searching (and without being too choosy about styles).

Now that what I wear better reflects who I am, I have come to love clothes and clothes shopping. The only downside is that having enough clothes (and not enough money), I need to be able to restrain myself! Retail therapy is temporarily off limits.

One response to “I would go out tonight …”

  1. Love this post. I’m so glad you’re finally able to wear the clothes that you love and that suit you! Keep enjoying it, and keep loving fab x