Shorts have often caused a great deal of contention amongst those who take an interest in sartorial matters. As the famously witty Savile Row designer and aesthete Hardy Amies wrote in his 1964 style bible, the ABC of Men’s Fashion, “The natural desire to relax is often the cause of the abandonment of all standards of taste” and declared that a man “should never wear shorts except [when] actually on the beach or a walking tour”.

This largely stems from the fact that in the recent past, shorts were considered the preserve of boys (think public school uniforms and the Scouts) and when the time came to switch to something longer, it was seen as a sort of rite of passage into manhood. Admittedly, even today, once you’ve passed the age of 15, they can be a tricky garment to style.

But with the continued relaxation of dress codes, shorts have become not only acceptable as everyday wear - when the mercury is on the rise - but stylish too. They are even seen as acceptable office attire (well, at some offices) which was unthinkable only a few decades ago.

Curiously, the idea of a shorter garment for your lower half actually predates trousers. Modern trousers as we know them evolved during the Victorian period, but previous to this, a curious ensemble - known as ‘stockings and breeches’ - was the norm for well-to-do men in western society.

This dual-component outfit consisted of a short-type garment – breeches – which finished just below the knee and was fastened around the leg, usually by buttons, a drawstring – or in some cases, ornate brooches. Knitted wool stockings were worn in conjunction with breeches, which completely covered the leg. It was only after the French revolution of 1789 that trousers became more widespread for men of all classes in Europe, prior to this they were worn only by working men.

The Caribbean island of Bermuda – which is today more associated with its infamous ‘black hole’ triangle and off-shore banking – did much to popularise the idea shorts for the modern world. This now iconic style was supposedly the brainchild of Nathaniel Coxton, who ran a tea shop on the island in the early 19th century, catering to the British Navy. The sailors complained about the intense heat in the establishment, so Coxton’s solution was to cut their standard issue trousers off 3 inches above the knee – and Bermuda shorts were born. Later, the full regalia worn with this fetching garment included a tailored blazer, club tie, dress shirt, knee-high socks and leather loafers – this became the national costume of Bermuda until 2007.

Although this sounds like a rather singular look, it caught on and spread to other British colonial outposts located in sultry climes in the 1930s and by the ‘50s had become a firm fixture of the civilian wardrobe. Even Winston Churchill was known to approve: “The short pant is a terrible fashion choice unless it is from Bermuda.” This style is the ancestor of the modern shorts we wear today and provided the blueprint for the many iterations since.

Given the numerous potential style pitfalls that come with wearing shorts, we thought a few helpful styling tips would be beneficial to help you steer clear of any overgrown schoolboy connotations.

You might think that seeing as a coast is the natural home of shorts, it would be easy to get the look right, but it’s still relatively easy to veer down the wrong path. We say ditch the slogan tees and flip-flops for a striped band-collar shirt or polo shirt – like the sort worn by Jude Law in The Talented Mr. Ripley. As for footwear, boat shoes or canvas espadrilles should be your go-to. They’re smart but still locale-appropriate.

Shorts in an urban environment have always been tricky to pull off, but with a little-considered styling, it’s an easy look to master. A lightweight long-sleeve linen shirt – like our Portofino shirt is just the ticket. Nonchalantly roll the sleeves to just beneath your elbow and finish with a smart pair of penny loafers or boat shoes, worn with a pair of invisible socks. This will keep up the illusion you’re going sans socks (bang on trend for summer) but is considerably more comfortable. A sleek leather attaché bag and wouldn’t go amiss either and will ensure your look errs on the right side of smart.

Depending on whether your alfresco soiree is an informal barbecue or a somewhat dressier garden party, you’ll want to adapt your look accordingly. Printed shirts – and particularly those of the Hawaiian variety – have made a comeback in a big way and worn with a pair of our lightweight cotton shorts, will be a look that will fit your surroundings to a tee. Although we probably wouldn’t recommend going down the full Bermuda suit route now (those knee-length socks are going to raise some eyebrows), if you want to make more of a well-groomed impression, a crisp Oxford cotton shirt or a silk-cashmere polo is the way to go. Just remember not to roll your short cuffs to keep the look polished.