Trends are often a bit scary, aren’t they? What designers send down the runway, or what the fashion set start wearing on the street isn’t what most men have in mind, with the consequence being that some of fashion’s more out-there trends are dismissed as ridiculous. And, of course, they sometimes are. When Vetements brought out a T-shirt printed with the DHL logo and sold it for £185 back in 2015, everybody scoffed. But, weirdly, it captured something of the moment and became an overnight must-have. Now, it’s one of the most defining pieces of clothing of the past decade. Ditto for those tiny, tiny bags that Jacquemus has recently become known for.

Sometimes, a trend will come onto our radar and we’ll think it’s completely unwearable and silly, and yet, actually, there’s something about it that makes us want to try it out ourselves. The problem is that just because something finds itself “in fashion”, it doesn’t become magically easier to wear. And with baggy shorts, hiking sneakers and oversized tailoring currently doing the rounds with the fashion set, things can be tricky to navigate. Still, we’re never ones to shy away from a challenge at MR PORTER, so we’ve done you the service of breaking each trend down, and giving a few pointers on how you might pull it off. Because where there’s a trend, you’ll bet that there’s also a way to wear it well.

GQ called them “fashion’s final faux pas” back in May, noting how just-below-the-knee, basketballer-esque shorts were somehow in vogue, and as much as you may try and fight it, it’s true. They’re everywhere fashion week, and a litany of established fashion designers – from the Italian glamour of Gucci to the darkwear charm of Rick Owens – are driving the trend. Wearing them, however, presents a conundrum, namely that you run the risk of making your legs look all sad and stubby and generally dragging your silhouette into the ground. First, it’s best to keep things casual; wear your T-shirts (graphic if you like) and shirts untucked, and keep them ever so slightly oversized to avoid looking out of proportion. Keep everything relatively sporty, too – this is an instance where it’s best if you commit. Also, go mad with your socks. A man wearing baggy shorts and wacky socks is a man who doesn’t give a damn, and frankly my dear, there’s nothing more fashionable than that.

Hiking sneakers used to be the most hideous thing a man could wear. They were purely functional to the point that it was almost aggressive, and only ever came in that swampish shade of opaque couche. In 2019, however, the hiking sneaker is high fashion, and Balenciaga and Gucci have stolen it from your local rambling society and planted it firmly on the runway. Also see its offshoot: the hiking sandal. Clunky and comfortable (and certainly not for everyone), it’s wise to wear both hiking sandals and sneakers with sports socks to keep things streetwise. In the rest of your outfit, feel free to mix it up – a relaxed pair of tailored trousers is a surprisingly effective juxtaposition, as is an oversized shirt.

One of the biggest trends of the past year, oversized tailoring marks a return to the smarter side of menswear of yore, but with a contemporary edge. The line between looking up to the minute and like you’re a kid wearing your dad’s blazer is, however, frustratingly fine. To avoid this and keep things looking louche, keep colours calm and muted – avoid loud prints and think minimal. Don’t be afraid of 1980s-style shoulders and statement-making lapels on your blazer, but wear a T-shirt underneath to make it look modern. Clean white sneakers work well – they’ll ground an oversized tailoring look, peek out nicely from a pair of billowy trousers, and will channel the right air of comfy sophistication.

The men featured in this story are not associated with and do not endorse MR PORTER or the products shown