The last time we bought a family car, a decade ago now, we got an automatic one instead of a manual one. So much easier to drive. A no-brainer, really. But I completely failed to anticipate, somehow, that by switching to an automatic I would forget how to use gears. I deskilled myself by accident.

And now I’ve gone and done the same thing all over again, except my error this time is in a much more serious field. This time it’s about handbags, which are obviously much more important than the trifling matter of cars. Sometime around the end of the noughties, you see, Mulberry brought out the Alexa satchel, and the cross-body bag was suddenly everywhere. After years of hooking a strap over my shoulder and clamping a handbag to my side under my arm, I switched to a cross-body with a strap long enough that you could sling your bag across your body like a sash, so that it bumped merrily against your hip as you walked along without you having to hold on to it.

A much under-discussed factor in what makes a good handbag is how comfortable, or not, it is to carry. This matters just as much, if not more, than what it looks like. Every bag has an ergonomic comfort level, and a psychological comfort level. Ergonomic comfort starts with weight: a bag with too much chunky hardware can tip the scales into backache territory before you’ve even started filling it. And it is also about how the weight is distributed. A cross-body bag, which evens out the burden across the two halves of your body, is almost always more comfortable than a shoulder bag, which means you can carry around all the kit you need to feel prepared for life.

The psychological comfort level of a handbag relates to the fact that it contains your valuables and your essentials. Security matters. An open-to-the-world straw basket may have a more chilled “vibe” but it requires you to be vigilant on its behalf. A cross-body bag is a revelation, because it can’t be snatched in the way that a shoulder bag can, so as well as freeing up both your hands, it liberates you from needing to keep antennae quivering every time a stranger gets too close.

But after years of merry lolloping with a succession of cross-body bags, I have left myself deskilled for the return of the shoulder bag. When I hook a bag over my shoulder now, I crunch that side of my body into a lopsided huddle like an awkward child trying on high heels. And I am so out of practice with having to streamline my stuff into a bag small enough to fit snugly under an arm that I have forgotten the art of packing light for work or a night out.

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A refresher course in shoulder bag wearing starts with finding a bag that nestles comfortably by your side with a soft, inch-wide strap that nestles into the dip of your shoulder line – not a stringy one that digs in, or a stiff wide one that slips down. Next, take everything out of your old bag and do a brutal purge of what you actually use. I kept a powder compact in my bag because I thought that was what grownups did, until one day I realised I hadn’t opened it in over a year.

The brutal aesthetic truth is that the wonky diagonal slash of a cross body strap makes every outfit about 70% less chic, so the style argument for the return of the shoulder bag is valid. This is a skill you can relearn, I promise – like riding a bike. Driving a car, sadly, is a different story.

Model: Ana at Body London. Hair and makeup: Sophie Higginson using Sam McKnight and Tom Ford Beauty. Top: Whistles. Bag: Mango

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