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I freely admit that casual clothes are not my speciality. There’s less to know, really, than about tailoring and formal dress, and it’s easier to do to a passable level. The areas that are saturated with insider knowledge, like denim and trainers, have never held that much appeal for me. Too far removed from tailoring. Too hard to combine well with a good blazer.

However, there are times when I have little choice but to think about what casual clothes to wear. One of those is when the temperature just gets too hot for trousers. We’re getting to that point in the UK: it’s been hot now and again for a few weeks; there was one week in May when it was scorching for five days straight; and sometime in July you know the sun’s just going to kick into overdrive.

I’m happy to wear shorts in those circumstances (and when not at the office). I am not so classicly minded that I refuse to wear anything but long socks and long trousers all summer long. But I do think there is something to be learnt from tailoring when buying the right shorts.

When I was a kid everyone wore bermuda shorts – long, baggy, free-flowing. Today anyone that’s interested in fashion tends to go for ‘tailored’ shorts, an adjective stolen from high-street shirts that is just used to mean narrow. Problem is, narrow shorts of any length aren’t usually that flattering. Few men have thighs they are proud of, more often because they are too thin rather than too fat, and narrow shorts just emphasise this. They make slim legs look plain thin.

No one would ever make suit trousers that were that thin to the knee. So why make shorts that way? Trust me, tailors know how to flatter a very unflattering leg. Suit trousers may be that thin at the ankle, but never at the knee where the tailor knows more room is needed to be able to flex properly.

If shorts are to be thin, a tailor pointed out to me, they should be short too. They need to be mid-thigh rather than to the knee. Because then there is no problem with flexing and no narrowness to the shape. They are still ‘fitted’ or ‘tailored’ as there is little excess cloth, but there’s no need to make slim legs look like drainpipes.

So this is my rule of thumb for you: the slimmer you want your shorts to be, the shorter they should be too. The middle-aged Italians you may see on the cobbles of San Remo know this well. Or at least, it’s built into their culture enough that they don’t have to know it.

Slim shirts and slim polo shirts do not work with wide shorts. Unless you are trying to replicate the Oxford bags look and deliberately exaggerate your proportions (which, my uncanny psychic sense tells me you are not), keep your shorts in a similar silhouette to the rest of your clothes (which, if you are reading this, is probably more fitted than those that don’t).

There’s a few nice, simple pairs at American Apparel. Keep them short and classic.