While it might seem as though skate culture – or at least skate culture-inspired style – is omnipresent today, it hasn’t always been that way. Skateboarding was once a rinky-dink children’s craze, and only got serious in the 1970s when LA surfers started pulling tricks in empty swimming pools when the waves were flat. By the 1990s, lighter, narrower freestyle boards with smaller, harder, faster wheels allowed for more speed and greater control, and street skateboarding began to dominate public spaces, turning entire city suburbs into sandbox skateparks. By the turn of the century, it was reported that more American teenagers skated than played basketball.

With every street corner suddenly seized, the scene exploded and skateboarding began to spill out into wider youth culture. Skate punks became commonplace in TV, cinema, music and video games, from Jackass to the fringes of Clueless, from the two-minute, three-chord tracks of NOFX, Pennywise and Sublime to the joypad toggling of Tony Hawk’s Pro Skater, a remastered version of which is due to land later this year. But perhaps skating’s greatest legacy came in the form of clothing, where the chunky-soled plimsolls adopted to cushion skaters’ feet were firmly planted in the social consciousness and the easy, oversized outfits worn in the halfpipes came to shape the silhouette of the era.

Even so, skaters have historically been outsiders – not just because time spent perfecting backflips in empty car parks. But now, their baggy jeans, billowing shorts and washed-out hues are mainstream, even cool. And with the 1990s aesthetic showing no sign of abating in the present day, the style is resurfacing again in this season’s trends.

With that in mind, here are some tricks you can pick up from skate punks that won’t end up with you falling face-first into a concrete floor.

Given that their music is littered with samples – 1989’s Paul’s Boutique, particularly, is a masterpiece woven from stolen sounds – it makes sense that the Beastie Boys were also magpies when it came to the way they dressed. As the recent film Beastie Boys Story reveals, some of their theft was dubious at best – not just the 1970s disco outfits prised from an abandoned closet in the rented Hollywood home they were living in while recording Paul’s Boutique, but the markers of black culture they clumsily reappropriated early on in their career as they pivoted toward hip-hop (durags and all). But by the early 1990s, they’d got the formula right, sitting somewhere in the overlap on a Venn diagram of the predominant counterculture musical genres of the decade: grunge, hip-hop, alt rock and punk. The lesson here is that it doesn’t matter where you draw your inspiration from, as long as you treat it with respect.

In 2010, Mr Bob Burnquist became the first skater to successfully land a 900-degree reverse-natural rotation, aka a “fakie 900”, and only the fifth person of any discipline to execute the trick. Over a 30-year career, he’s picked up some 14 gold medals at the X Games, not to mention built the world’s largest skateboard ramp in his back garden. However, to the wider public, he’s possibly best known for his signature “Burntwist” lip move in the 1999 PlayStation video game Tony Hawk’s Pro Skater (more on that later). And while he might not be able to pull off this impossible manoeuvre in real life, he did set a template for how to dress should you wish to look like you can. The carpenter’s pants weren’t fooling anyone – what tool is going to stay put at that angle? But the breezy, oversized and well ventilated clothing ensured that Mr Burnquist’s legendary aerial mastery wasn’t the only big air he experienced.

The notorious 1995 film Kids didn’t just bring the talents of Mr Harmony Korine, Ms Chloë Sevigny and Ms Rosario Dawson to the fore, it provided a snapshot of what teenagers in New York were up to (or at least confirmed their parents’ worst nightmares). While not a core skateboarding text in the way the worn-out Alien Workshop and World Industries VHS videos passed around school playgrounds were, the sport was written into the film’s DNA. Most of the cast, including writer Mr Korine himself, were skaters, and the outfits worn – expansive tees, washed denim and Chuck Taylors – come with a degree of authenticity perhaps missing from other examples drawn from the 1990s teen canon (ahem, Encino Man). The film, however, is often uncomfortable in a way its easy-going wardrobe isn’t, and we certainly don’t suggest you use your deck in the manner depicted in the movie – to beat a man to a bloody pulp. As for the drug use, we’d take the style over the substances any day.

Hollywood doesn’t always get sports right; for every Raging Bull there are dozens of Wimbledons. As such, you could be tempted to dismiss 1989’s Gleaming The Cube as little more than a vehicle for Mr Christian Slater. But look around the edges and it becomes clear that at least the casting department was paying attention. Skate legends including Messrs Mike McGill and Lance Mountain feature, alongside future Black Flag frontman Mr Mike Vallely, skater turned musician Mr Tommy Guerrero and one Mr Tony Hawk, who appears as Buddy, a skateboarding Pizza Hut delivery boy. Mr Hawk, who has kept in contact with Mr Slater ever since, maintains that whether the film’s lead performed his own stunts is one of the things that he is most often asked about. (Freestyle icon Mr Rodney Mullen in fact stood in for Mr Slater for many scenes, as if the blond wig didn’t make this fact obvious.)

One way to prove that the 10,000-hour rule – the principle, popularised by Mr Malcolm Gladwell, that it takes 20 hours a week for 10 years to truly master something – really does hold up is to take up skateboarding. But back in the late 1990s, armchair enthusiasts were given the opportunity to nail the sport in considerably less time. And without the bruises and broken limbs, unless you count RSI. Tony Hawk’s Pro Skater provided players with instant access to skate culture, and in turn made the titular athlete a household name. From the early 1980s onward, Mr Hawk had stood out for his outlandish tricks, earning him the nickname “Birdman”. He became the first skateboarder to land a 900 in the same year the first of his video game franchise came out. In 2011, Transworld Skateboarding magazine called him the second most influential skateboarder of all time after his peer Mr Mark Gonzales, but outside of the sport, it’s hard to argue that anyone else comes close. So, yes, go big or go home, but also learn how to market yourself.

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