Wearing shorts? Tread carefully if you’re past 30

As we get older, style becomes somewhat less helter-skelter and more of a tightrope walk; we can no longer afford to give everything a go the way we used to. For while fashion in your 20s has a devilish sense of humour and a certain level of arrogance, once we hit our 30s, the old “could I, should I, would I?” mantra firmly plants its feet for the duration. Fashion, seemingly overnight, seems to lose its sense of humour and, it seems, so do we.

Take city shorts as an example – an item that definitely blurs a few boundaries. Although not an easy styling challenge, it is possible you can pull off the right pair, as long as you are sure to adhere to a few important dos and don’ts. Know that boots will only shorten your legs, so stick to flat pumps or sandals. If you are a fan of the downtown Los Angeles vibe, pair with some classic Converse sneakers – somewhat of a cliché, I’ll admit, but always a success. When it comes to denim, don’t over-distress. A (natural) rip here and there or a bit of fraying is fine, but there is never any need to massacre. For hot weather, linen, cotton and silk are the best options, but when you can stick to wool or a wool-cashmere mix, do so. Finally, look for a reasonable length in a roomy fit and wear a jacket at all times, otherwise you run into beachwear territory.

Now for the boys – listen up, for this is important. Ultimately, there is no room for argument for dressy shorts. I’m telling you now, warning you, in fact: the rules regarding shorts are very much one-sided in that there are no exceptions or experiments. When it comes to the rules of male dress, anything without a solid purpose is always somewhat questionable. Think embellishment, hats (unless for protection from the weather) novelty ties or more than one piece of jewellry. Likewise, you should never wear shorts for shorts’ sake. And don’t even think of teaming the look with a blazer. If an event is dressy enough for a blazer, it is more than likely worth a pair of trousers.

However, I understand to eliminate something so practical would be foolish. On a boat, at a relaxed barbeque or at the beach, shorts are perfectly acceptable. Just be sure to remember they are supposed to hit just above the knee – not too long and certainly not too short. You are not an American merchant marine.

Tread carefully with your choice of shirt. Short-sleeved shirts are rather iffy when paired with shorts. Softer fabrics generally look better in casual wear; you don’t want to go near anything with an ironed crease. Instead, stick to a long-sleeved shirt in linen or breathable cotton, and roll up the sleeves. A good, simple rule to follow is to pair your belt with your shoes. It’s always best to stick with traditional colours schemes such as black, dark brown or a rich tan. No crazy with a K here, please.

The truth is, a lot of the time shorts verge precariously toward the inappropriate side of things; an awkward distraction, if you like. So, to be frank, if you haven’t seen your 20s in a while, it’s more than likely shorts are rarely going to work. And again, I urge you, I beg you, before you face ridicule (from the girls; the boys probably won’t notice) you may want to try out the look at home first and be truly honest with yourself. A moment’s hesitation should be your defining answer.

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