No two entities go together quite so swimmingly or stylishly as the summertime and a quality pair of shorts. As soon as the mercury edges its merry way into the mid-twenties, that sweet Celsius spot where it’s warm enough to bare flesh without burning, it’s time to free your legs from their fabric cages and feel the breeze between your knees. Skies out: thighs out, as The Rake’s summer motto has it.

For such a simple garment (literally trousers, but shorter), it’s incredible how much anxiety shorts can provoke. First, there is the question of length, of finding the elusive spot between the knee and the waist which cools the lower legs while preserving a gentleman’s modesty. Then the question of material: however comfortable, a pair made from jersey will simply never do outside of the privacy of your own home, but a tailored pair made from suiting fabric will be too stiff and stuffy for summertime activities. Then the trickiest question of all: what to wear shorts with.

Happily, the sun shone on some of the most sartorially competent men in the world at Pitti Uomo in Florence the other week, facilitating a masterclass in the wearing of shorts for summer. Taking our cue from these heroic liberators of the lower leg, we’ve come up with a style guide to wearing shorts this summer. The most important thing is to advertise your thighs without being chastised, weatherwise. Or, put less poetically, check the goddamn forecast. Few sights are more tragic than a shivering pair of bare legs cowering under shelter in an April shower. Also, don’t fall into the trap of thinking that shorts must mean sandals. As the examples below will show you, there are more elegant ways of styling your shorts that don’t involve leather straps slicing into your instep.

The Bermuda

The Bermuda is an example of a high-risk, high-reward kind of short. You need a spirit of adventure to wear these shorts that is redolent of the fearless Gurkhas who famously wore the style as part of their army uniform. As the gentleman pictured above capably demonstrates, the best way to wear Bermuda shorts is to capitalise on their military heritage. For a more refined take, eschew camo print for a tailored military style jacket by Simeonethat will pair perfectly with the smart pleats on these cotton Bermudas from Rubinacci. Dress the look down with a simple white SunspelT-shirt that will contrast superbly with the navy shorts when you take the jacket off.