I’m going to tell you something about my personal life that no one outside my family knows. Some people might think it embarrassing but it’s relevant here because of the furore over Eddie Izzard. It’s also relevant because it seems to me we’re never going to solve the questions of gender and sex until we tackle a deeper issue that is still troubling and strange (especially in Scotland).

So here we go. When I was little, about five or six, and at a primary school in Aberdeen, one of my favourite things to do was dressing up, and I can still remember the details: the classroom with the wall of windows, the cardboard boxes in the corner we’d transform into rockets and houses and cars, and the trunk full of hats and fancy dress. It felt like we were left to play for hours in those days, the early, sunny ‘70s.

But the thing is: the outfits I liked to put on weren’t the astronauts or the cowboys but the dresses and the ladies’ shoes. I remember my teacher (Mrs Reid, we love you!) telling my mother about this fact without, it seems to me, any hint of censoriousness or concern (although perhaps they had different conversations out of my earshot who knows). Perhaps they realised it was just a boy dressing up before he knew what was “right” and “wrong”.

Now here’s another memory. I’m a bit older, at a different school. We’re putting on a play of some sort and I’m rummaging in another trunk full of fancy dress. I instinctively go for the long robe/dress but the feeling is different. No doubt by this point – I’d be about seven or eight – I was starting to pick up what the rules were: certain clothes for boys, certain ones for girls. I remember the familiar joy of dressing up, but there was something else in there as well now. What’s the right word? Shame?

Whatever the feeling was, I can still, remarkably, feel it now, 45 years later. Indeed, the shame, or embarrassment, from the past lingers so much that I almost didn’t write this column – I guess because there’s part of me, still, that doesn’t want to risk judgement or mockery or sniggers or an obvious breaking of the “rules”. But it has to be worth it in the end as a way of talking about how much has changed – and how much hasn’t.

Take the continuing controversy over Eddie Izzard I mentioned. Eddie, as you’ll know, is campaigning to be the Labour candidate in Sheffield, but the fact that the comedian is trans has meant a lot of the discussion has been around the issues of gender, sex, trans rights, and women’s rights. It’s also hyper-relevant this week because the Scottish Government has been debating its proposed law to allow trans people to self-identify.

The controversy around Eddie also took on an extra, interesting edge in recent days when an old interview re-emerged on social media. In it, Eddie talks about switching between “boy mode” and “girl mode” and when the interviewer asks how this is done, Eddie suggests one way is by changing shoes i.e. high heels equals girl mode and flats equals boy mode.

Some women have reacted angrily to this idea – there’s more to being a woman than wearing high heels, they say – and not only is this a fair reaction, it seems to me that more of us should be talking about the strange way in which we, women and men, continue to behave around clothes and shoes. Sadly, confusingly, the attitudes I started to pick up when I was seven or eight in the 70s are still around, possibly as strong as ever.

In many ways, Eddie Izzard is one of the positives of this story as a pioneer and a progressive and, wonderfully, the opposite of shame and embarrassment. I’ve seen Eddie’s stage show many times, it’s very funny, but often the serious point amid the comedy is that all of us should have “total clothing rights” i.e. you can wear what you want when you want. Eddie would sometimes say “They’re not women’s clothes. They’re my clothes. I bought them.” And quite right too.

But it appears that – wonderful and progressive as Eddie’s approach to life is – the stereotypes around clothes and make-up and shoes and all the rest of it still linger even in Eddie’s case – the idea for example that high heels are “girl” and flats “boy”. Undoubtedly, a lot of it has been changing – it’s much more common than it was even five years ago to see men in public places wearing “women’s clothes” or make-up or whatever. Lots of young men in particular do not appear to give a fig for the clothing rules anymore and that’s brilliant.

But do not underestimate how deep this issue goes for men, particularly Scottish men. I was at a ceilidh recently and was talking to a group of guys, all of whom were in kilts, including me. As we were talking, the trans issue came up and a couple of the men expressed the view that they would never wear women’s clothes. I then made the rather obvious point that they were telling me they would never wear a skirt while, in fact, wearing a skirt, albeit one that we choose to call a kilt.

Until we move on from this kind of attitude it’s going to be hard to progress on the issue of gender and sex, and I mean everyone here: men, women, Eddie, me, everyone. We got over ourselves long ago about what women can and do wear – they can wear anything – but the problematic attitudes about what men can and do wear still linger. I know this because of how I feel about the child-me dressing up in the 70s. I know it because of men in skirts saying they would never wear skirts. And I know it because of comedians or anyone else thinking high heels are in some ways linked solely to women rather than men.

The sad thing is I’m not at all confident that we will in fact move on from those attitudes any time soon, particularly in a country as conservative about masculinity as Scotland. Slowly, slowly, slowly, progress is being made on trans rights and the dysphoria and distress many trans people feel. But I worry that it’s always going to be harder to help and support trans people as long as we continue to have out-dated, confusing and shame-inducing attitudes to something as simple as clothes.

Perhaps I'm wrong. Perhaps in the future everyone, men and women, will have the same clothing rights. Perhaps high heels and flats will be just shoes. And perhaps, if it happens, we can talk more sensibly and calmly and progressively about gender and sex.

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