Pleated trousers are, like many things in menswear, not exactly new. For most of the 20th century, in fact, they were a dominant theme in the trouser department, chiefly because – before the proliferation of synthetic and stretchy fabrics – they were a handy way of adding volume and ease of movement to a garment. They are most certainly on the trend agenda once more, thanks to designers such as Dries Van Noten, the exceptionally pleat-happy Rubinacci along with casualwear brands including Monitaly and Barena.

So, why now? The newfound acceptance of pleats is, in part, thanks to the recent diversification of men’s wardrobe: the emergence of baggier cuts, inspired by streetwear; an increasing willingness to experiment when it comes to tailoring. Of course, men are also simply realising that pleated trousers have certain things going for them that skin-tight ones do not: they’re not only comfortable, but, when worn right, very flattering. Read on for our primer on how to make them for you.

Thought you couldn’t get more classic than a navy blazer, blue shirt and sand-coloured chinos? Think again. Swap the latter for some pleated trousers (add some braces for good measure) and you’ve got yourself menswear classicism at its finest. With less care, this man could easily end up looking like his grandfather, but he avoids that by thoroughly understanding the principle and particulars of pleats: the key to the streamlined fit is the placement and direction. In this instance they’re reversed, meaning the folds face the pockets, preventing billowing around the waist, and keeping the entire outfit trim and proper, with just a slight dash of the undone via the unbuttoned shirt.

Some friends finish each other’s sentences; others engage in a kind of sartorial symbiosis. These chaps have clearly been taking styling cues from each other – both looks are a variation on the same theme, right down to the nonchalantly folded-back cuffs and, crucially, the double-pleated trousers. If we were to assign this double act a persona it would be characterised as “Dickie Greenleaf and Tom Ripley experiment with utility-inspired outerwear” – it’s louche, relaxed and just a tad caddish. The trick is the careful juxtaposition of casual and smarter elements: the precisely tailored folds are nicely tempered by tucked-in, unbuttoned linen shirts, while the buff-to-brown colour palette conveys a summery ease. The short double pleats, which extend straight from the waistband, give a very subtle shape to the waist without interrupting the slim lines of the trousers themselves. It’s all very concise and clever. We just hope they don’t spill anything…

Sunshine plus slim-fitting trousers equals a potentially sticky situation. Much better to keep things breezy with pleated trousers in, say, linen or, as this wise gent has done, shorts. That said, go too voluminous and you’ll appear to be wearing culottes, a garment even the most ardent of pleat practitioners would struggle to pull off. Instead, opt for blink-and-you’ll-miss-them single darts to provide just enough breathing room in the heat while keeping the silhouette of your shorts streamlined.

This man is walking with such purpose that we might speculate he’s on his way to teach a how-to-wear-brown-in-town masterclass. Where do we sign up? Here, again, we see not one but two pleats at the waistband, but these have been opened up lower down the thigh, making for a longer, leaner and smarter shape to the trousers. It’s a good way to build pleats into a slightly sharper tailored look. And the cappuccino colour scheme helps, too.

Imagine for a moment that this man had reached for his trusty blue jeans in the morning, instead of settling on these workwear-inspired, army surplus-style chinos. Do you suppose he’d have caught the lenses of the street photographers? In that “sliding doors” reality, we wouldn’t be here telling you about how easy it is to wear pleated trousers in casual contexts – just add an oversized white tee.

Blue blazer, white shirt and beige trousers déjà vu? We’ve seen this all before, right? Wrong. Here, we see how to carry off the lesser-spotted wide-leg pleated trouser with aplomb. The key is, of course, to cuff them. Practically a prerequisite when wearing trousers of the baggy variety, the turn-ups create a gentle taper and prevent this gent from seemingly being swallowed in swathes of fabric. The woven belt, too, acts as an anchor – drawing in the folded fabric – and is a useful tool in any pleat-wearer’s arsenal. Slip on some Common Projects sneakers and you’re good to go.

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