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How to wear shorts and not look like an idiot

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Sam Diss
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Google Search’s auto-correct function is full of shorts specific content: full of hows, whys, and whens. It’d seem that men, at the best of times panicked by their own body and the clothes they own to cover them, have no idea how to wear shorts. 

Which is why we wrote this. Which is why you’re here.

Legendary tennis player Arthur Ashe with Wimbledon trophy and a great pair of shorts. (Rex)

When can’t I wear shorts?

To weddings, funerals, or to the office. Just get yourself some lightweight, slightly looser fitting trousers for those situations – pure cotton, maybe a linen blend. No shorts unless it’s a funeral for someone you didn’t really like or, like, a particularly avid jogger and you’re going to bust out a memorial 10k straight after the wake. Sorry.

Or if you’re a mob boss, according to Carmine Lupertazzi in The Sopranos. “A don doesn’t wear shorts,” he said. Even if he’s BBQing.

OK, so when can I wear them?

Opinions differ, but parties, pubs, casual offices, working lunches, maybe the odd nightclub, are all fine for shorts. It has to be hot, though – really hot. If you’re an “always wears shorts” guy – the kind who cycles to work, say – and it’s not super hot, you can still get away with them in the office or certain social occasions, but anything that involves interaction with the gen-pop is largely out. They’ll just look at you funny. 

For different situations there are different shorts (we’ll get to that later…)

FARAH Hawk Chino Shorts; £39

What are the different kinds of shorts?

Later is now: The short is a deceptively diverse device. When it’s warm, you’ve got chino shorts, cargo shorts, jean shorts, suit shorts, football shorts, swimming shorts, plaid shorts, linen shorts, seersucker shorts. These are split into genre specific shorts (swimming shorts, football shorts); fancy shorts for when you’re at a nice garden party (seersucker shorts, suit shorts); shorts for lounging around the house in (cargo shorts, linen shorts); shorts for multiple social occasions (chino shorts); and shorts for no occasions (plaid shorts, jean shorts).

Cos Turn-Up Linen Shorts; £55 (Click to buy)

What if my legs look weird?

They’re almost certainly fine; stop worrying.

Wait, did you say suit shorts?

Yes, but not a full suit. There was a time – a time when Pharrell was everywhere – when people tried to convince people that a regular summer suit with truncated legs was a perfectly acceptable way to dress, but it’s largely not. We’re going to put a picture below of a normal-looking-albeit-really-cool-guy (renowned modern formalwear designer Thom Browne) in them but, honestly, trust us, you won’t even look as good as that, because nobody except models, #influencers, and people with nothing to do but stand there while a tailor measures their thighs all day does. Even Thom’s struggling. When we say “suit shorts” we mean suiting material (which serves pretty much the same purpose as chino shorts, only made of cotton).

New York designer Thom Browne. (Rex)

How long should they be?

Depends on your proportions and how nice your legs are, but usually between one and four inches above your knee. Never below the knee unless you are a surfer, Nick Wooster, or a teen Juggalo.

And how tight?

Remember that bit in Friends where Phoebe dates a guy who always wears shorts and everyone keeps getting an absolute eyeful of his Central Perks? And how about the uncomfortability of the seam of your trousers riding up into your sack, feeling like it’s gonna cut you in two, a feeling that increases five-fold with the more transient short. It’s fucking crap, right? Neither are ideal. This is the tricky camel-tail-or-bollock-drop conundrum.

You need to find something that is tight enough to still look cool, while loose enough to stop you from suffocating. And you need something where the hip-to-bum seam fits you just right: this is harder said than done, seeing as everyone has different length butts. Your safest bet is buying something that fits you no shorter than mid-thigh with about a half-inch gap between your nuts and the very bottom of the zipper seam and an inch gap around the thigh ‘cuff’ leaving you with a little bit of room for your legs to breathe without going too far.

All that’s a very long way of saying: unless you’re anatomically perfect, you need to try them on. (So, yeah, you need to try them on)

Oliver Cheshire in chino shorts and white Nike Air Max trainers. (Rex)

What shoes do I wear with them?

You’re going to want to wear something a little bit low-profile – as in, low-cut; not like a spy – and preferably in a light shade where possible. White trainers, sandy lace-ups, tan loafers – bread and butter for summer style. You want to roughly match the formality of your shorts to your footwear, especially with dress shoes: that no hard-sole shoes with linen shorts or anything casual, but they’re okay with smarter styles. Trainers go with pretty much everything – especially brilliant white ones – so go nuts.

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Sam Diss

The Associate Editor of New Projects at ShortList, Sam enjoys making up words to annoy editors, writing features about sports, music, weird things, and cool people, and listening to Mark Morrison's 'Return Of The Mack'. He's also a fairly capable centreback. Follow Sam on Twitter: @SamDiss

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