Postbag: Is it OK to wear shorts on a date?

I get asked a lot of questions, both on Twitter and over email. Usually it’s things like “Is that your real eye?” or “Who’s that famous person you mention in this blog?” and other times it’s women in America trying to get me to link to their blogs about nannies, or contraception, or gay marriage. And then, very occasionally, it’s even more random than that. Sometimes, it’s just a question, like: “Is it OK to wear shorts on a date?” Well, it’s a valid question. Thank you to the shy young man who sent it. I’m not usually one for doling out fashion advice, but here goes nothing.

The trouble with shorts and the weather
Short trousers present plenty of problems to anyone, let alone an earnest young singleton (I am not talking about myself here) who so desperately wants to make the right impression. First, British summers are hysterically volatile. Like a cat waking up from castration or a cantankerous grandfather who told you not to play in that shed, you never quite know which way it’s going to go. On a grey, breezy morning, should you risk slipping on a pair of shorts in the hope the cloud will burn off later? Or do you play safe and stick to trusty trousers, running the risk of sweltering by lunchtime, your calves gasping for air, for freedom?

Legs: is there room for improvement?
And even if you’re an all-weather shorts-wearer, the kind of guy who’d be found lumbering around supermarket aisles in March in your very best frayed cargo shorts in delightful camouflage print, there are the aesthetics to think about. Lily-white legs, knobbly boulders of knees and gnarled toes are celebrated as an aphrodisiac in precisely zero cultures.

Should you fake tan? Get some kind of pedicure? Well, maybe a little bit of both if you’re looking to impress. Fake tan is more divisive than pro-life and #twittersilence, but if your legs are a particularly lovely shade of blue and you want to wear shorts, there’s no harm in slicking on a really thin layer for a subtle bronzed look. Get a female friend you trust to do this for you – you do not want to look like you’re angling for your own reality show, or bathe in Tropicana. As for toes, if yours are really heinous, then maybe a pedicure would be like sticking a rosette on a pile of sick. Just get some good shoes or canvas shoes. And don’t have any sock showing unless you have really great legs or are kind of ‘hip’ – or are very young – otherwise it will look like a MISTAKE, or like an indignant British taxpayer enjoying a beach in his ‘beyoodiful’ home country in sandals and terry-towelling socks.

So, are shorts appropriate for a date?
If they’re the right kind of shorts, yes. It also depends on where you’re going and when. If you’re meeting during daylight hours and temperature allows, then go for it, unless you’re going to a ‘fancy’ restaurant or think you’ll be out very, very late. Bare knees and goosebumps on a night bus might seem pathetically romantic but it’s just misery with a little bit more mascara on. If it’s in the evening, wear a collared shirt with your shorts – a polo shirt will do, too. The exception, of course, is if you’re one of those young bucks with ‘bodies’ who likes to wear those vests that look as if they blew off a stripper’s washing line in a gale and just happened to land on you. A T-shirt is fine if it’s plain, and fits you, and you’re pretty, but probably best left for the daytime. The trick with any date is to dress as inoffensively as possible, but still be you and stylish.

Play it down
A lot of people think a date is a great time to try lots of, er, self-expression and really show off their ‘unique style’ (shared by around 80 other people in the very same pub as them) but until you’re a few weeks down the line, it probably isn’t. Go too outré on the clothes and your actual personality will be vying for attention with the one you dragged out of your wardrobe. Overdressing can also be seen as a sign you’re overcompensating.

Shorts, of course, play havoc with this idea of playing it down because, despite our best efforts to integrate wearing shorts into society, it is still rather unusual for boys to be bare-legged. This is why your shorts need to be fairly low-key, flattering and, most importantly, fit you. There’s something about the sight of a man’s knees and calves that can drive some men and women wild – so use this leg power to your full advantage.

So, in answer to your question, dear enquirer, it is OK to wear shorts on a date, yes. Happy to help.