A 43-year-old man who does not own a motorbike in a leather biker jacket: acceptable or thoroughly unfashionable and the sign of an impending midlife crisis?

B, N1

Oh, B! I welcome your question, not just for me, but for the sake of you and all your fellow menfolk. The tedious gender stereotype is that women obsess over their clothes whereas men just throw on whatever smells least. As Jerry Seinfeld – a young up-and-comer who was mentioned in last week’s column and who I’m sure you’ll be hearing more from – once said: “Men wear their underwear until it absolutely disintegrates. Men hang on to underwear until, until each individual underwear molecule is so strained it can barely retain the properties of a solid. It actually becomes underwear vapour. We don’t even throw it out, we just open a window and it goes out like dandelion spores.” (My previously mooted plan to spend the whole of January on my sofa watching Seinfeld has now been extended to the whole of the winter.)

Now, far be it for me to doubt the wisdom of Seinfeld, or express expertise in men’s underwear, but I find that it is men who are far more anxious about fashion rules, and, specifically, breaking them. Women, in my sweepingly generalised experience, see fashion as a means for having fun; men see it as a perilous challenge fraught with the potential for humiliation. They have so little faith in their judgment about clothes that they assume anything that isn’t jeans and a T-shirt or a button-down shirt from Gap will result in mass shaming and having to wear a red F (for FASHION) on their forehead. Thus, the rules must be sought and clung to, like vines across a crocodile-infested swamp.

Your concerns about buying a biker jacket are a perfect example. You like biker jackets. You want a biker jacket. You have (I’m assuming) the means to purchase one. And yet – you doubt yourself. Do not doubt yourself, B. Life is made for making oneself happy, not castigating one’s personal taste. Will some of your male colleagues raise their eyebrows at your new jacket? Will some of them make jokes about a “midlife crisis”? Probably, because men are ridiculous, and they are clinging to this vine that associates leather jackets and fortysomething men with Jeremy Clarkson and mental breakdowns.

This is silly. The only purpose fashion rules serve is if they provide aesthetic – not moral – guidance. So, saying double denim looks terrible is an aesthetic guideline. But saying “don’t wear leather jackets because that means xyz about you” is absurd. (And as for the aesthetic rules – these, too, are made to be broken.)

So sod ’em all. The point about your age, B, is not that you’re having a midlife crisis, but that you’re a big boy now, and big boys are old enough to know what they want to wear and should do just that. Live a little! And let me tell you something a teacher told me when I was eight, and it’s as true about clothes as it was about My Little Ponies: if someone teases you about something you have, it just means they’re jealous.

I read recently that Donald Trump said all female members of staff must “dress like women”. What does this actually mean?

Sarah, by email

What indeed, Sarah, what indeed. There has been a surprising amount of talk in recent weeks about what it means to dress like a woman, and, funnily enough, a lot of this talk has been coming from men. How kind of these menfolk to take a break from explaining to us why the Women’s March isn’t the right kind of feminism to tell us what, exactly, real women wear. Thank you, men!

As you say, Sarah, a report last week said that Trump insists that the women lucky enough to work for him must “dress like women”. This means, apparently, “looking neat and orderly” and feeling “pressure to wear dresses”.

This comes conveniently close on the (stiletto) heels of the joint report, published by the Women and Equalities and Petitions Committees, that found women are – still – being told to wear high heels and makeup, which makes sense because everyone knows a woman can’t possibly do any work unless she’s half-hobbled and has stabbed herself in the eye several times with a mascara wand. Various male commentators felt compelled to put in their tuppence about how they totally agree with these rules, which was great because women enjoy nothing more than getting tips on femininity from blotchy-faced, middle-aged attention-seekers.

Ivanka Trump … ticking all the boxes. Photograph: Pawel Dwulit/AP

It’s funny, but these sorts of rules about how women should dress always make me think of one woman specifically: Ivanka Trump. She ticks all the boxes, with her feminine dresses, feminine heels and feminine hair. She really is a certain kind of man’s ideal, isn’t she? Funnily enough, she doesn’t seem to be women’s ideal, given that both Nordstrom and Neiman Marcus, two major US shopping centres, announced last week that they’re dropping the First Daughter’s fashion line reportedly owing to poor sales. But that’s so us, isn’t it, gals? We just don’t recognise femininity when we see it. Fortunately, there are plenty of men around to set us right.

Post your questions to Hadley Freeman, Ask Hadley, The Guardian, Kings Place, 90 York Way, London N1 9GU. Email ask.hadley@theguardian.com.