The Knack

The Grown Man’s Guide To Wearing Shorts

How to navigate one of summer’s trickiest sartorial challenges – and emerge with your dignity intact

It is perhaps the single most controversial issue in men’s style, and one on which several thousands of words have been written, both for and against: should grown men wear shorts? To those in favour, they’re a practical alternative to trousers during the warm summer months. To those against, they’re dorky, infantile, ugly, or any combination of the above.

We won’t contribute any more to the debate. If you don’t like wearing shorts, another few hundred words aren’t going to convince you to change your mind. If you do like wearing them, however, and you’d like to continue to do so without fear of being ostracized or ridiculed, the following guide might just be of help.


Let’s get back to basics. The first thing to ask yourself when choosing a pair of shorts – or any piece of clothing, for that matter – is how well they suit the proportions of your 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 one with a shorter inseam or with hems that can be neatly cuffed. If you’ve got pale legs, consider using a tinted moisturiser. If you’ve got skinny legs, try building a few more squats and deadlifts into your workout regime. Etcetera, etcetera.

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, and as such it’s highly unlikely that a certain 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 legs day. Trust us. We work in the same office.

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  • Rubinacci Manny Pleated Cotton-Twill Bermuda Shorts


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, shorts were frowned upon in all but the most casual of settings. In his 1964 treatise on style, ABC of Men’s FashionMr 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 as recently as 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 like these seem quaint by today’s standards, and it’s hard to imagine that they ever represented the popular consensus. Still, it’s important to treat views that are not our own with respect. In the rush to reject old ideas in favour of new ones, it can be easy to forget that men like Messrs Amies 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 expressly 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 in these situations 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 that you’ve been invited to a garden party. The weather is set fine. Should you wear shorts? Ask yourself: is it better to feel the breeze around your ankles, or to avoid the icy stare of your host? Unless you’re in intimate company, is it not better to err on the side of caution?

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 a few 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 that 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. Context is everything, and unless you’re absolutely sure that you’re not going to get fired then it’s perhaps best not to break with convention. Most offices are so harshly air-conditioned that shorts aren’t necessary, anyway.

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OK, so you’ve completed the painful but all-important self-assessment. You’ve given some consideration to the circumstances in which it’s appropriate (and not appropriate) to wear shorts. What now? Get your credit card out, because we’re going shopping. Before you jump in at the deep end, though, it’s worth getting to grips with the basics. The following five styles have proven resilient to the ebb and flow of seasonal fashion, and taken together should be more or less all you need to get by. 

First, your workhorse: a pair of navy cotton-twill shorts. Pick a pair that finish 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. While you’re here, pick up the same or a similar pair in a neutral shade: beige, stone, sand, ecru, or whatever the designer felt like calling it. These two pairs have the benefit of going with more or less anything, and look especially good with billowy Oxford shirts, à la Mr Armie Hammer in Call Me By Your Name. (Avoid wearing beige chino shorts with a white polo shirt, though, unless you want to look like the pool boy at a chain hotel.)

Next, grab a pair of cargo shorts in olive green. Yes, yes, we know, cargo shorts are the devil. There were even semi-serious calls to ban them a couple of years ago for crimes against style. But before you write them off, look at the company that they keep. Socks and sandals? Once anathema to fashionistas, now the height of style thanks to Prada. Crocs? Reinvented last year by 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. With that in mind, you can expect cargo shorts to be on the mood board of all the most forward-thinking brands for SS19.

Not that you should be wearing cargo shorts for the cool factor. These are utility shorts, best worn with similarly utilitarian garments. They look terrible 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 finishes above the knee rather than below it. Repeat after us: below-the-knee cargo shorts do not look good.

Denim cut-offs are a great choice for weekends in the park, and if you don’t already own a pair it’s quite easy to get one. Just take some old jeans – the older the better – 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.

Finally, in a reflection of the increasing influence that sportswear is having on the way we dress – yes, that old chestnut – we recommend rounding out your collection with a pair of loopback-cotton jersey shorts. These can look a little slovenly if you’re not careful, so opt for a more refined pair from a designer such as Thom Browne.

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Men have a history of using their legs as a way of injecting a little colour into their outfit. 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 into 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, though, and it’s still possible to overdo it. Avoid big colours, unless you feel that you have the big personality to back them up. Try a washed-out pastel pink over a pillbox red, or a pale lemon over a New York taxi cab yellow. And 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 points, most of them applicable in some degree to shorts.

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And so to the whimsical world of seasonal fashion, which has decreed that 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 or suede espadrilles – think Tom Ford or Bottega Veneta – 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 that we can all get on board with.

Having said that, current-season fashion should always be taken with a pinch of salt – especially when it’s 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. Firstly, bear in mind that they tend to finish much higher than the average pair of shorts. You’ll be exposing a great deal more flesh, making any points that may have arisen during your self-assessment (see above) all the more relevant.

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

That being 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, keep in mind that a plain colour – ideally navy or black – will take you further than a vibrant floral pattern.

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In short