It is perhaps the single most controversial issue in men’s style, a debate to which thousands of column inches have been devoted over the years: should grown men wear shorts? The answer will vary depending on who you ask, but here at MR PORTER, we’re firmly in the “yes” camp. We should add, though, that it’s not quite as simple as just saying yes. Not all shorts are created equal, and as with all matters of style, it’s how you do it that really matters. To that end, we’ve created a definitive, five-point guide to getting it right.

For further reading, check out our guide to the best shoes to wear with shorts or get more detailed style advice in our five-point guide on how to wear shorts. For now, though, let’s get started with the first and most important consideration when choosing a pair of shorts: you.

The first thing any man should ask himself when choosing a pair of shorts – or any piece of clothing, for that matter – is how well they suit the proportions of his body. This means engaging in an honest appraisal of your legs. Stand in front of a full-length mirror and take a look at them. How long are they? Are they tanned or pale? How much hair do they have? Do you have slender calves? Knobbly knees? The thighs of a rugby player?

The conclusions to be drawn from this exercise should be fairly obvious. If you’ve got muscular thighs, slim-fit shorts are going to be uncomfortably tight, so choose a more generously proportioned pair. If you’ve got short legs, a pair of shorts designed to finish just above the knee will finish lower, so choose some with a shorter inseam or with hems that can be neatly cuffed. If you’ve got pale legs, avoid white shorts and choose a pair in a colour that provides a little more contrast, such as navy or black.

None of this is intended to give you a complex, just a better understanding of your own body. Men’s legs come in all shapes and sizes, so it’s highly unlikely that one pair of shorts will look the same on you as they do on the next guy. More to the point, they certainly won’t look the same as they do on the guy who models them for MR PORTER. He’s 6ft 2in, just got back from a two-week beach holiday and definitely does not skip leg day. Trust us. We work in the same office.

We 21st-century men live in an age of sartorial enlightenment, and this is no more evident than in the emancipation of our lower legs. In years gone by, men’s shorts were frowned upon in all but the most casual of settings. In his 1964 treatise on style, ABC Of Men’s Fashion, Sir Hardy Amies wrote that a man should “never wear shorts except actually on the beach or on a walking tour”. Mr Tom Ford echoed the sentiment in 2011 when he said in an interview with AnOther Magazine that “shorts should only be worn on the tennis court or on the beach”.

Comments such as these seem quaint by today’s standards and it’s hard to imagine that they ever represented the popular consensus. It’s questionable whether Ford stands by his views of more than a decade ago.

Still, in the rush to reject old ideas in favour of new ones, it can be easy to forget that men such as Sir Hardy and Ford might have had a point. Maybe shorts aren’t as formal as full-length trousers. Maybe they shouldn’t be worn everywhere. Maybe your office’s failure to ban them should not be taken as an invitation to wear them.

There’s no one-size-fits-all rule for wearing shorts, which is probably the reason why they’re so contentious. Given that this is an adult’s guide, perhaps the best advice we can give you is to act like an adult, which means giving full consideration to the nature and context of your actions before going ahead with them. Imagine, for example, you’ve been invited to a garden party. The weather is set fair. Should you wear shorts? Ask yourself: is your host a dapper gent who favours a formal dress code? Or is the occasion a more casual affair? Perhaps a pair of smart chino shorts would do well.

Now, how about at work? “Is it OK to wear shorts to the office?” is a question that MR PORTER’s editors have been fielding for many years now and, if we’re being honest, we’re yet to come up with a proper answer. The best we can do is say: it depends.

It depends on a lot of things. The office you work in and the people you share it with, first and foremost, but also the shorts you’re planning to wear and what you’re planning to wear them with. Tailored shorts have been seen on runways of late and might be the perfect choice, but context is everything and, if in doubt, then it’s perhaps best not to break with convention. Most offices are so harshly air-conditioned that shorts aren’t necessary anyway.

You’ve completed the painful but important self-assessment. You’ve given some consideration to the circumstances in which it’s appropriate (and inappropriate) to wear shorts. What now? The next step is to get your credit card out, because we’re going shopping. The following four styles have proved resilient to the ebb and flow of seasonal fashion and, taken together, should be more or less all you need.

First, your workhorse: a pair of neatly tailored chino shorts or similar tailored cotton-twill or poplin shorts. Pick a pair that finishes two or three inches above the knee in a cut that complements the shape of your legs. What does that mean, exactly? In a nutshell, it means that if you’re slim, choose a slim fit. If you aren’t, don’t. Feel free to try wider-legged or more directional styles if you like, however.

What about colour? Navy never fails, but you might also consider picking up the same or a similar pair in a lighter shade: beige, stone, sand, ecru or whatever the designer felt like calling it that day. These two colours are both neutrals, and they have the benefit of going with more or less anything: they look especially good with billowy Oxford shirts. Avoid wearing beige chino shorts with a white polo shirt unless you want to look like the pool boy at a chain hotel.

Next, grab a pair of cargo shorts. This style has been the subject of much derision over past years. But before you write them off, look at the company they keep. Socks and sandals? Once anathema to fashionistas, now the height of style. Crocs? Ridiculed at first, then reinvented by fashion designers such as Mr Christopher Kane.

One of the unwritten rules of the fashion industry is that as soon as something reaches the nadir of style, an intrepid designer is sure to pluck it out of the gutter and make it cool again. And so to cargo shorts, which are firmly back in favour and form a key component of the utilitarian look being presented by brands such as Stone Island. They’ve also been taken up in tailored guises by brands such as Dries Van Noten and Loro Piana, or with a streetwear edge by CELINE HOMME and Fear of God.

When dressing them up, bear in mind that cargo shorts are utility shorts and usually look best worn with similarly utilitarian garments. They don’t look good against the elegant sportiness of a polo shirt, for instance. Regarding length, cargo shorts will invariably finish a little lower than more formal styles, but again, try to find a pair that finish above the knee rather than below it, unless you’re going all-in on an oversized look.

The next pair you’ll need are denim shorts. There are plenty of designer options available right now, or you could just as easily make them yourself. Cut-offs are a great choice for weekends in the park. Just take some old jeans and cut the legs off with a sharp pair of scissors. Don’t worry about being too neat – frayed ends are all a part of the look. With denim shorts, the one rule is to make sure they’re loosely cut and casual – whether they’re longer, baggier skate styles or a neater above the knee pair, a skin-tight jean short is not a good look. As for how to wear them, we’d suggest a laid-back surf aesthetic by throwing an oversized tie-dyed T-shirt over your denim shorts.

Finally, we recommend rounding out your collection with a pair of loopback-cotton jersey shorts or other sports shorts. Pair with a sweatshirt or crisp tee for a casual, sporty look or opt for a more refined pair from a designer such as AMI PARIS or SAINT LAURENT.

Men have a history of using their legs as a way of injecting a little colour into their outfits. On Nantucket, an elite resort island off the coast of Cape Cod in Massachusetts, wealthy holidaymakers wear shorts or chinos in a shade of washed-out lobster pink known as Nantucket Reds. Their more adventurous neighbours on Martha’s Vineyard might opt for a pair in lime green or a brightly coloured Madras plaid or perhaps a pair embroidered with tiny whales, lobsters or anchors. Describing these garish garments in a 1976 article for Esquire, the late journalist and author Mr Tom Wolfe wrote that they had a “go to hell” air about them, presumably because if you didn’t like them, then… Well, you get the picture.

Our advice? Embrace colour and pattern, but do so with care. Shorts are a great way of adding a little vibrancy to your look. Not only are they inherently casual, but they have the added advantage of being quite small in surface area and a long way from your face when you wear them, so any colour you do employ should feel fairly unobtrusive.

Just remember that not everybody’s as open-minded as they are on Martha’s Vineyard, so it’s still possible to overdo it. Avoid big colours, unless you have the big personality to back them up. Try a washed-out pastel pink over a pillar box red or a pale lemon over a New York taxi-cab yellow. And when you wear colour – this doesn’t just go for shorts, by the way – keep the rest of your outfit understated.

For more help on this topic, read our exhaustive guide on how to wear colour, which covers a range of topics, most of them applicable in some degree to shorts.

Haven’t you heard? Swim shorts are no longer just for swimming. With the addition of a short-sleeved shirt, a pair of retro-inspired sunglasses and some leather sandals, slides or mules – think TOM FORD, Bottega Veneta or Manolo Blahnik – they can now take you from the beach to the bar with ease.

At MR PORTER, we’re in favour of any development that enables us to dress in a way that’s more versatile and less beholden to stuffy rules. This is especially true during summer, when ease and simplicity should be high on your list of priorities when choosing what to wear. At first glance, then, this is a trend we can all get on board with.

Having said that, new developments in fashion should always be taken with a pinch of salt, especially when they’re being driven by forward-thinking brands such as Prada and Dries Van Noten. A few considerations, then, before you jet off to the beach with nothing but a couple of pairs of swimmers in your suitcase. First, bear in mind that they tend to finish much higher than the average pair of men’s shorts. You’ll be exposing a great deal more flesh, making any points that may have arisen during your self-assessment (see point 01.) all the more relevant.

Second, consider the material. Most swim shorts are cut from a lightweight, quick-drying nylon, rather than a more substantial cotton-twill, which gives them a cling factor that, when combined with the shortness of the cut, can prove hazardous when sitting down. Finally, let’s reiterate something we’ve already mentioned, which is to consider the occasion. This is very much a holiday look and it’s less appropriate the farther you are from a body of water.

That said, there are degrees of formality even within the confines of swim shorts. The British casualwear brand Orlebar Brown was the pioneer in creating “shorts that you can swim in” and its flat-fronted Bulldog shorts, complete with side tabs, zip fly and popper fastening, are a world away from those with a drawstring or elasticated waistband.

Fabric is a consideration, too. Thom Browne’s seersucker swim shorts are inherently smarter and more versatile than a pair in shiny nylon. And don’t forget colour and pattern. If you do intend to wear your swim shorts away from the pool, a plain colour – ideally navy or black – will take you farther than a vibrant floral pattern.