We’ve gone to great lengths to bring you the best ways to wear this season’s generously proportioned trend.

Baggy trousers? Madness, you say! Stay with us, though. After more than a decade in the sartorial hinterlands, wide legs seem to be making something of a comeback. What started seasons ago as a trickle of pleats and dropped crotches turned into a torrent of generously cut trousers in the most recent AW collections, with brands including Gucci, Balenciaga and Craig Green all getting in on the act. It’s a simple enough trend, but one that requires careful consideration. To help, we’ve rounded up a few examples we’ve spotted on the streets of London, Paris and Milan.

Dressing well is often a matter of judicious contrasts. Logically then, if you’re wearing wide-leg trousers, shouldn’t you opt for a slightly more streamlined top half? Not if you’re to follow the example of the above street-style fixture, who combines his voluminous corduroy trousers with an oversized cricket sweater (not entirely accidentally ticking off three key trends of the season).

Crucially, there is a break – a crease in the fabric where hem meets shoe – as there should be with heavier fabrics in wider cuts (unless, of course, you’re going for the trendier ankle-swinger cut beloved by the likes of Mr Junya Watanabe). Not keen on corduroy? Denim (preferably in a mid-wash) or a wool-flannel fabric will achieve a similar effect.

September marks the arrival of autumn, but forecasts promising a dazzling Indian summer (in the UK at least) could put new-season dressing off the agenda for a few more weeks.

Fortunately, we can confirm that this capacious new silhouette works just as well in cotton and other lightweight fabrics. These brown trousers, pleated, wide-hemmed and slightly cropped to reveal a sliver of ankle, have been teamed with a deck-striped shirt perfect for the last vestiges of warm weather. The half-tuck of the shirt is a nice touch, retaining a bit of shape at the waist while allowing for circulation.

The enduring appeal of chinos lies in their versatility – they can be reworked to fit in with almost any trend but remain constantly stylish. But if you’re going to wear them with a more substantial pair of shoes – such as the above pair of boots from Red Wing Shoes – you’ll need to opt for a pair with a wider leg. The single pleats on the above, cropped example (which have been appropriately styled with double turn-ups to give them a very slight taper) help them to not feel too shapeless. Note again the judicious tucking-in of the sweater – as pleats give you a more shapely waist, this is usually a good idea.

A denim jacket is a structured, seam-adorned piece. A pair of wide-leg corduroy trousers is not. That’s why they work so well together in the above image. Simple black sneakers, an untucked shirt and a loose leather belt amplify the easy-going vibe of this particular look, a carefully-considered approach masquerading as nonchalance.

Rest assured – we’re not about to herald the return of Hammer pants, but rather inform you of a take on this dropped-crotch silhouette that works particularly well. In fact, for anyone worried about going big all-over, an alternative is to choose trousers with a subtly dropped crotch that taper down to a slimmer leg, giving the illusion of volume without swamping you in fabric. In the image above, this street-style maven has played to the top-heavy idea by wearing such a trouser with a loose sweater and soft-shouldered, cardigan-like wool coat.