Streetwear is a strange and complex beast. On the one hand, it’s disposable, obnoxious and often unflattering. On the other, Supreme – the skate brand that James Jebbia launched in the nineties – is now a billion-dollar behemoth. It collaborates with Louis Vuitton and, if you believe the rumour mill, even has a link-up with Rolex pending.

It’s no fad, either. Though born 50 years ago in Californian surf culture, streetwear didn’t truly blow up until the noughties, when the first skate boom (thank you, Tony Hawk) and hip-hop’s chart dominance turned a generation onto baggy jeans and graphic tees.

Today, that generation is hitting adulthood proper. And though it might have a mortgage, it still feels more comfortable in a hoodie than a suit.

“Streetwear is so many people’s go-to each day because dress codes have become so much more relaxed,” says Harvey Nichols menswear buyer Lara Djandji. “The amount of customers looking for tailoring has decreased as more and more people are wearing jeans with a jacket to work, and those who previously wore jeans are now more inclined to shop for a tracksuit.”

Fortunately, streetwear itself has grown up, too. So whether you’re looking to adjust your style, or just refine your jeans-and-a-sweatshirt wardrobe, here are six ways to do it without looking like a try-hard.

Rule One: Luxe Up Your Fabrics

Streetwear staples were, until recently, things you could happily fall off a skateboard while wearing; hence why most were rendered in denim and heavy cottons, in non-constrictive fits. But modern streetwear has stepped out of the skatepark and designers have reworked time-honoured pieces – hoodies, cargo trousers, trainers – into garments you wouldn’t want to risk on the concrete.

Today, for the everyday wearer, that means upgrading utilitarian fabrics to something more premium. “An easy way to incorporate a subtle element of streetwear is through a pair of high-end sweatpants,” says Mr Porter style director Olie Arnold, referencing styles cut from soft-handle materials like cashmere and jersey. “They can substitute for a well-worn pair of chinos.”

It’s a move that’s been endorsed across the board, from brands like Loro Piana and Officine Generale, who now craft baseball caps as well-made as their blazers, to the high street, which no longer stuffs loopback cotton into the pyjama section.

Outfit Inspiration

How to wear premium hoodies and trackpants

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Rule Two: Don’t Be A Hypebeast

For youth culture, hype is everything. Recognition is currency, so you need to cop the brands that your peers know about: Supreme, Palace, Gosha, Yeezy. But the exchange rate changes over time. “There isn’t an age cut-off for streetwear,” says stylist and photographer Chris Tang. “But an older guy should stick to what they like and what works for them.”

The grown-up move is to fly below-the-radar, by wearing labels that are innovative but don’t have teenagers queued up outside their stores. “A lot of brands this season are taking influence from streetwear,” says Arnold, who points to easy-going urban wares from labels like Pop Trading Company and stripped-back pieces from Acne Studios.

In short: you should aim to get the look without the logos, or at least keep them tucked away as subtle details. Because an adult knows the best thing about grail finds isn’t shouting about where they’re from, but being asked.

Outfit Inspiration

How to wear streetwear like a grown up

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Rule Three: Start From The Bottom

In the words of Drake: “Started from the bottom, now we’re here.” And the man’s got a point. “In streetwear, shoes make the outfit, and sneakers are the lynchpin of it all,” says Arnold. But this can be dangerous terrain to navigate. Hypebeasts hyperventilate over each new drop, and you can invest grotesque amounts of time (not to mention money) trying to keep up.

Instead of paying resale price for Yeezys or the latest Off-White collaboration, plump for trainers that will last as long as your brogues by favouring premium materials and brands that prioritise build quality. “The lines between luxury mainstream fashion and streetwear have blurred beyond recognition for a number of seasons now,” adds Arnold.

Despite the rise of purposely ‘ugly’ trainers and chunky soles, it’s wise to avoid adornment or odd shapes to guarantee your box-fresh kicks will look as good with your suit as your joggers.

Outfit Inspiration

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Rule Four: Think Loose, Not Baggy

Teenage boys don’t need to stress their silhouette, so they can afford to browse the oversized rail. However, the loose fits of modern streetwear aren’t forgiving to those entering their dadbod phase of life. “Streetwear is, dare I say it, a ‘lifestyle’,” says Tang. “It resonates with people from all walks of life.” Just make sure you get it right for you.

Your best move is a silhouette that’s more relaxed than the figure-hugging tailoring of a few years ago, but doesn’t make you look like a tent with legs.

It’s easiest to pull off below-the-belt. Brands from the high-end to the high street have swung from slim fits to straight-leg shapes that offer more movement on a skateboard – and are more comfortable off one. An oversized bomber is the teenage accompaniment; for those older, try a cropped jacket to balance out the looseness.

Outfit Inspiration

How to wear loose streetwear pants

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Rule Five: Bring The Streets To Work

Streetwear’s tendrils have crept into every corner of menswear, which means that there are now few outfits that can’t be adapted to the look. Which is good news if you’ve spent the last decade cultivating a wardrobe of soft-shouldered Italian tailoring and are loathe to toss it all out.

“Incorporating streetwear into your [work] wardrobe can be a tad intimidating,” says Arnold. “A hoodie is a simple item to invest in that can transform more traditional attire. For an amateur hoodie-wearer I would recommend using it for layering; try under a luxe bomber jacket or textured unstructured blazer.”

Trainers are another simple way to make your office togs a touch more contemporary. “A pair of sneakers with a relaxed suit or chinos is always a safe and easy option,” adds Arnold.

Outfit Inspiration

How to wear a hoodie at work

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Rule 6: Keep It Simple(ish)

The swiftest route to try-hard status is a look straight off the shelf. Streetwear is about the mix-and-match; pieces from different brands and cultures that together reflect your own allegiances and interests.

“Don’t go flashy and wear head-to-toe the latest gear,” says Tang. It’s a look that only works for Instagram influencers, who are probably all still too young to drive.

That’s not to say you can’t rock statement or logo pieces. But as a grown-up, you should pair them with stuff that shows a bit more creativity. The ‘it’ hoodie that’s a must-have for fashion editors works better with chinos more readily seen on skaters (who have no idea what the ‘frow’ is) than trousers and sneakers from the same brand. If you’re dressed like a lookbook, dial things back.

Outfit Inspiration

How to wear statement and logo streetwear in a grown up way

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