Eight thoroughly urban labels and how to wear them in style.

You can trace the origin of streetwear to the 1980s hip-hop scene on both coasts of the US. The two are inextricably linked. Tracksuits, zip-up tops and sloganed T-shirts became the uniform for groups such as Run-DMC in Queens and by N.W.A in Compton, and were then duly adopted by skaters, 1990s grunge singers and metal bands, as well as many grumpy teenagers in the years that followed.

Lately, streetwear has had a resurgence. In a big way and with a new, much broader legion of fans, who are falling over themselves to snap up avant-garde, yet decidedly streetwear-inspired pieces from the likes of Vetements and Balenciaga.

This is why we thought it was high time we issued some guidance on how to incorporate some streetwear into your wardrobe. It can be a tad intimidating if you’ve been surviving on a steady diet of tailoring for the past decade, but here are eight of our favourite streetwear brands and some tips on how to wear them.

Having acted as distributors for skate superbrands Palace and Magenta Skateboards for several years, in 2003, Messrs Peter Kolk and Ric van Rest decided to strike out on their own, launching Pop Trading Company in their hometown of Amsterdam. “In skateboarding, pop means having a certain snap,” says Mr Kolk. “If you have good pop, you have a great jump.” The brand dances the thin line between the skateboarding world and contemporary menswear. “Our interests not only lie in skateboarding, but in well-made garments, too,” says Mr Kolk. The pair have created a distinct aesthetic: stripped-back streetwear, minimal prints and a focus on a simple, sans-serif logo. For their latest collection, they looked to military garments and 1990s skateboarding videos for inspiration. “There is a lot of tour-of-duty olive in there, and the graphics come from an old video magazine called 411VM, which came on VHS tape, that we used to watch growing up skating,” says Mr Kolk. “It covered all the cool stuff from contests to rider profiles.” The signature – and most adaptable – piece is the Falling Down jacket, which you could wear on the street skating or as a light outer layer for work.

Launched in 2011, Cav Empt is the brainchild of enigmatic graphic designer Sk8thing, a figure shrouded in Banksy-like mystery, and Mr Toby Feltwell, the music-industry titan who discovered grime artist Dizzee Rascal. The Japanese brand now has a sizeable cult following, which appreciates its knack for intricate composite garments and graphic tees adorned with surreal prints and floating slogans. This season’s prints are inspired by 1990s rave culture, something Mr Feltwell enjoyed in his teenage years. Fix up and look sharp (excuse us) in this vivid acid-yellow cotton-corduroy overshirt that features a distorted – and somewhat trippy – skyscraper appliqué on the back. Dial it down with a pair of dark trousers and plain white sneakers.

In 1980, California-born Mr Shawn Stussy was making waves on the surf scene with the short boards he designed from his home in Laguna Beach. A decade later, when he transferred his iconic graffiti logo – Stüssy, with an added umlaut – and reggae prints to surf clothes, the brand went stratospheric. Worn by DJs, club kids, skaters and creatives including Messrs Hiroshi Fujiwara, Michael Kopelman and Luca Benini, it has never been out of style. This season, the brand is exploring Japanese subcultures through a Californian lens, and has created garage jackets and sweatshirts in washed-out SoCal pastels that retain that languorous, surf-slacker casualness that it has become famous for.

Los Angeles-based Fear of God was created by Mr Jerry Lorenzo in 2013, since when, the label has established a trademark aesthetic with an emphasis on layering and reworked proportions that has attracted A-list devotees such as Messrs Kanye West, Kendrick Lamar and Zayn Malik. Mr Lorenzo’s most recent collection is a mash-up of 1990s activewear, streetwear and classic Americana, all of which have have been given a luxe spin. Key pieces include denim jackets lined in faux shearling and alpaca, checked cotton-flannel shirts finished with denim collars and drawstring track pants in red jersey. The overall result is a refined take on the clothes worn by John Bender in The Breakfast Club.

The designers at Japanese brand Wacko Maria, ex J.League football players Messrs Keiji Ishizuka and Atsuhiko Mori, are a wry pair. The brand, established in 2005, is best described as gloriously rockabilly does streetwear, and it stands out for its mixture of stylish, minimal cuts, bold graphics and strident, wicked slogans. We particularly like the coach jacket, above. Here, in lieu of a sports-team crest or emblem, you’ll find the signiture phrase “Guilty Parties” plastered across the back. The boxy shape hides a multitude of sins (although, admittedly, the tiger stripes won’t). Wear it with a white T-shirt and black jeans for a grrrreat look.

It’s hard to pin down Sasquatchfabrix., which is part of it allure. Founded in 2003 by Mr Daisuke Yokohama, it’s a Japanese label that unites East with West, referencing myriad influences from around the world, while nodding to its Japanese roots with droll details. The name is a portmanteau, “Sasquatch” being the elusive, maybe mythical animal said to inhabit the forests of the Pacific Northwest (aka Bigfoot) and “fabrix” referring to, well, cloth. Chief among this season’s products are the souvenir jackets embroidered with Fuji-esque volcanic landscapes and slouchy sweatshirts printed with dragons that recall traditional Japanese miniatures.

Menswear’s love affair with streetwear couldn’t have come at a better time for Ms Sofia Prantera, the renegade brain behind cult streetwear label Aries, which she founded in 2012 with Mr Fergus Purcell. “After a long time of feeling like I didn’t fit in, I feel that my work has now been validated,” she says. “The clash of influences, the return to sportswear, the slightly anarchic marketing ideas and business structure have all finally become acceptable practice.” Ms Prantera is inspired by 1990s outdoorwear and references it often in her work, the long-sleeve, graffitied skater T-shirts and acid-wash tie-dye shirts in her latest collection being a case in point. Wear with black chinos and classic Vans to ramp up your off-duty look.

“ALYX is a really personal project and personal brand, so the clothing is inherently emotional,” says Mr Matthew Williams, the brand’s creative director. The 31-year-old is formerly known for celebrity image-making (Mr Kanye West and Lady Gaga) and, alongside Off-White’s Mr Virgil Abloh, influential streetwear line Been Trill. His new label, which launched in 2015 and is named after his daughter, has gained a diverse clientele, thanks to its versatility and achingly cool separates. “My latest collection combines tactile influences with fabrication,” says Mr Williams. “There are subtle military references throughout.” By which he means the fabric – Italian Cordura, leather and silk – and the push-lock buckled belts on bombers, boot-camp-style sneakers and camouflage outwear. Top of our shopping list is this cotton twill bomber jacket, a collaboration with Alpha Industries, the official uniform contractor for the US military for more than half a century. Note the signature manufacturing details, including the trademark industrial zip-pull, here wrapped in leather. Camouflage is a busy pattern, so everything else should be quiet. Wear it over the brand’s white logoed T-shirt and a pair of black jeans.

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