The rake

The modern voice of classic elegance

StyleJuly 2018

How to Wear Shorts This Summer

Now that we’re on the wrong side of the summer solstice, it’s high time you said goodbye to constricting trousers and realised the emancipatory potential of bare legs. Here’s our guide on how to wear shorts.

captionNavy shirt paired with ecru shorts at Pitti Uomo.

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 Simeone that will pair perfectly with the smart pleats on these cotton Bermudas from Rubinacci. Dress the look down with a simple white Sunspel T-shirt that will contrast superbly with the navy shorts when you take the jacket off.

  • rubinacci-blue-denim-manny-cotton-shorts
  • sunspel-white-cotton-short-sleeve-classic-crew-neck-t-shirt
  • simeone-napoli-beige-nabuk-leather-military-jacket

The Utilitarian Approach

You don’t have to be labouring away in the sunshine to channel the utilitarian look, but if you do have business to attend to, a pair of shorts can put a playful spin on classic workwear that will keep you cool during boardroom meetings. Although shorts can work fantastically with suiting, the risk of looking like a public schoolboy is simply too great. Think safari instead of preppy. With a plethora of pockets, this combination of navy shirt from Marol and olive green shorts from Ka/Noa (with a high hemline to contrast nicely with the long-sleeve shirt) is as practical as it is stylish. A linen scarf from Kapital will introduce a pop of colour and still feel summery.

  • Ka-Noa-Dark-Olive-Cleman-Green-Shorts-With-Side-Pockets
  • marol-navy-safari-shirt
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Riviera Refinement

As well as dazzling onlookers in the sunshine, a pair of white shorts are perfectly evocative of the laid-back luxury of the French and Italian Rivieras. You can’t go wrong with a pair of crisp white shorts cut to sit just below the thigh (so as to not chop your legs in half at the knee): they will look eye-catching for all the right reasons. Wear with a patterned or Cuban collar shirt by Salvatore Piccolo to accentuate the Mediterranean feel, and bare your ankles in a pair of smart but comfortable brown leather loafers from New & Lingwood.

  • rubinacci-white-manny-cotton-shorts
  • Salvatore-Piccolo-Floral-Pattern-Cotton-Shirt
  • new-and-lingwood-chestnut-butterfly-calf-leather-loafers


Short and Tie

As these Pitti attendees prove, this combination of the ostensibly formal and the apparently casual work excellently well together in a way that recalls the stylish mods of the 1960s. The trick is to be mindful of colour and pattern. Use a plain tie with matching shorts to cut a clean line through a patterned shirt, or keep your underlayer neutral and introduce a patterned tie that complements your jacket. The clash of textures between these cotton shorts and silk tie by Calabrese 1924 will look great against the gentle backdrop of this light blue striped shirt from Santillo 1970.

  • rubinacci-red-manny-cotton-shorts
  • santillo-1970-white-and-blue-canary-wharf-cotton-shirt
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Desmond Huthwaite

Copywriter at The Rake

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