Fashion is totally obsessed with skateboarding. There’s been plenty of proof over the recent decade: in 2011, Céline’s ad campaign by Juergen Teller featured model Daria Werbowy candidly holding a bright-yellow deck; skater Dylan Rieder modelled for DKNY’s spring 2014 ad campaign with model Cara Delevigne; both Saint Laurent and Dior Homme have created an entire collection inspired by skateboarders in 2015 and 2016 respectively; and Louis Vuitton launched an official collaboration with Supreme under the artistic direction of Kim Jones, immediately followed by Virgil Abloh’s debut at the house which saw actual skaters walking down the runway, including British poster boys Blondey McCoy and Lucien Clarke.

While skateboarding has clearly become fashionable, the conversation about it is mostly self-contained within the fashion industry by people who have no skateboarding background whatsoever. For an industry whose job description includes calling out faux pas, sometimes it fails to realise it’s the one perpetrating it. It’s responsible for the surplus of models chilling at skate parks in impractical outfits, either holding decks in awkward poses and questionable positions— often mall-grabbing them—or standing at impossible locations to skate (gardens, rocky surfaces, sandy beaches… maybe they’re practicing ollies? Improbable). The list of errors is endless.
But of course, fashion is also a positive catalyst, helping the sport be more accepted by the mainstream. Even if the majority of the population reflects that by donning Thrasher T-shirts, blithely unaware of the fact that it is a skate magazine. Skateboarding has had to deal with a lot of misconceptions in the past as it’s always associated with rebellion, but now it’s definitely getting the supportive light that it deserves. The Olympics has recognised it as an official sport: skateboarding will debut at the 2020 Tokyo games. This is responsible for the rising interest in skateboarding courses, which helps to sell paraphernalia and clothing created by skaters, feeding the ecosystem.
With all this in mind, what do skaters make of the entire phenomenon? For the most part, the change in public perception is something they’re very excited about. “I used to get cussed all the time when I was younger,” says photographer Mun Kong. “Some random person would yell at me, ‘eh, skateboarders are losers!’ But that doesn’t happen anymore and I’m honestly so happy about it. Even though a lot of people still don’t understand the life we live, with outlets like Instagram people have become interested and are keen on finding out. In Japan, parents are sending their kids to skate school.”

“It’s a good thing that skateboarding is more accepted these days and more people might tune into it and find joy through skating,” says Yong Ng, founder of design consultancy firm Somewhere Else.
“It’s great to see Barry McGee collaborating with Uniqlo. When things move on to become mainstream, maybe the general public becomes a little more sophisticated. Meanwhile, a new generation of creatives is inventing a new language, that hopefully has a chance to stay under the radar to mature.”
Within the local skateboarding community, that very language is being defined with the presence of collectives. Aside from uniting skaters together, Triad produces a line of clothing and decks driven by nostalgia and humorous graphics (it’s made Snek Ikan decks, shirts with rickshaw service prints). “If you look good, you skate good,” adds Su’waidi Said, Triad member, jokingly. The venture Nocturnal Society similarly pays plenty of homages to various visual cultures: everything from post-Internet to 1880s surf culture and DIY. “It exists to add to the rich tapestry of skate visual paraphernalia that used to be lacking in the Singapore context,” explains founder, Suhaimi Saadan.
But with public attention comes the inclination to superficially associate with skateboarding to appear relevant, without bringing any benefit to the community. “Although it’s always good to get exposure from skateboarding, because we want to see more skateboarders, now it all boils down to social media. I guess it’s the brand’s interest,” says Hosni, also from Triad. “Sometimes the recognition aspect sucks because for us it’s a lifestyle, not a competitive sport. You have excellent skaters who have been doing it for 15 years and they don’t get anything… But what are we gonna do? We’re just going to skate. You can be ripped off anytime in lots of ways and that doesn’t just happen with skateboarding.” Su’waidi adds: “It’s mainly about the hype now and the biggest of it was Supreme x Louis Vuitton. But I think it’s an orchestrated joke by Supreme because they were previously sued.”
“I think everything, if it’s being presented contextually correct, with finesse and if it aligns with the mantra of that subculture in a non-exploitative manner, it sits well with me,” says Su. “It gets cringe-y when you see big fashion brands selling skate-related items when they don’t even participate in any skate-related activity—that is exploitative because they have not paid their dues to be in this realm. They have not come in to lend support in causes involving skateboarding. Photo shoots are no different, if they don’t adhere to the parameter I’ve listed then it gets stupid in a heartbeat.”
It’s easy to forget that skaters have already been major players in fashion, particularly in image-making. Legendary fashion photographers Mario Sorrenti, Glen Luchford and Alasdair McLellan are household names who skate—or were skating at one point. It’s also the case with local fashion photographers: many of them happen to be skaters. Unsurprisingly, they’re apprehensive about producing fashion images that are skate-related as it’s something they hold as very sacred.
Photographer Stefan Khoo has previously rejected skateboard- meets-fashion commissions, explaining, “I will find it hard to stage the authenticity. I didn’t dare to take (and never have taken) on [a skate-related fashion editorial] for fear of making it look bad. It’s better suited for non-commercial work where you can be more personal.” Khoo cites the work of photographer Ryan McGinley who has successfully captured the authenticity, since the subject really is the skateboarding community, shot in a documentary style. “For me, it’s only contrived to stage an authentic experience in an editorial with a model who has no skateboarding background as he won’t look the part. But it’s probably easier if you can bring a personal angle to it.”
“Sadly, not a lot of photographers know enough about skateboarding to infuse it seamlessly into their work,” notes Alvin Tang, who founded photography agency Verb Represent. “99 percent of the time it looks amateur-like. If you don’t know that much about it, then I strongly suggest that you don’t add it in,” he says, although that shouldn’t restrict your sources of inspiration for work as there are many ways to translate them in less literal ways. “I saw Ed Templeton’s Teenage Smokers series and I thought that it would be pretty fresh if I could shoot fashion or beauty in that manner… confronting and real.”
In contrast, Chuck Reyes, who’s now based in Paris, has pitched and shot a fashion editorial with skaters. “I was living in Ang Mo Kio for a year and I used to walk under the train tracks— it was a skate spot. At the time they set up a janky ramp and a grinding rail. It was covered so you could skate when it rains and it has nice lighting because it came from both sides. But they developed it and people don’t skate there anymore, which sucks.” Reyes then shared this location with an editor while they were conceptualising a shoot.
He reveals the process: “We needed an idea, a location and a direction had to be put. The clothes weren’t even skater-y, it was more streetwear. But because the location lent itself well to the direction of going with the skater thing, we went there. The model we casted asked her skater friends to join and they ended up wearing Prada nylon raincoats doing 360 flips in the background,” he recounted. “It wasn’t really a personal thing and it’s not like I really wanted it to. If we had a different location, we wouldn’t have gone that direction,” he admits. “Since there was that skater element to it, I didn’t want to make something embarrassing. Like if a skater would see it, my aim was that they wouldn’t cringe.”

The cringe is a big part of the discussion because the spirit of skateboarding encompasses making fun of things. And of course, the last thing you want is to be the butt of the community’s joke. The satirical Instagram accounts @whyidontskateboard and @asphaltposerclub perfectly epitomise this humour while highlighting the absurdity of society’s approach to skateboarding. Seriously, how many times have you seen a paid advertisement with someone randomly skating midway, completely unrelated to the narrative? Broadband subscriptions, face wash, bread, cars, bottled water… name literally anything, and it’s probably got a skate-related ad already. Although we want these mishaps to end, we kinda don’t want them to, either—what will we make fun of?
Jokes aside, at the end of the day, skateboarding is about fun and inclusivity: both positive attributes that are genuinely present while being constructed in fashion. “Obviously we don’t ostracise people because of their fashion choices. If you came to skate, then skate. Even if you’re wearing whatever your mom bought, it doesn’t matter,” concludes Hosni. Fashion should take cues from this open attitude, perhaps it must also open its forums for mutual understanding. “A conversation needs to take place first between two huge entities before either one can begin working together. Lacking an exchange of thoughts and ideas is when everything gets weird,” adds Su.
THOUGHTS OFF THE RAMP
ESQ: How does skateboarding influence your work or the way you work?
STEFAN KHOO: You bring into it the psyche and the attitude. It takes a lot of courage to jump down a flight of stairs on a speeding piece of wood on four wheels, and I try to keep that sort of brashness and rebelliousness in the way I work. The spirit of being wild and free, and just going for it.
YONG NG: Firstly, it’s the friends I’ve made—many of them are resilient and so creative. Their energy has been very infectious. Beyond that, skateboarding requires a lot of tenacity to do well, it’s a lot more falling than succeeding and that has helped me build character and has found its way into the work. Lastly, it’s the anti-status quo spirit that’s innate in skateboarding; it’s an energy that helps inform my pursuit.
ESQ: Why do you think fashion is so interested in skateboarding now?
STEFAN KHOO: I think that fashion has always had a fascination with youth culture and the alternative. In skateboarding, there’s a natural air of style, a defiance in attitude, and an appeal in the lifestyle that fashion wants a part of. There’s youth, beauty, harshness and an enviable sense of cool that transcends generations.
SUHAIMI SAADAN: High fashion has always been a world that is built on inaccessibility, fantasy and capitalistic credit. The rise in streetwear is probably an opportunity for big fashion houses to tap into, and the common denomination of streetwear is the staple T-shirt, pants, jeans, bermudas, sneakers and the occasional hoodie… everyday pieces of clothing that everyone can relate to. These items sit comfortably well in the realm of skateboarding where the points of differences are the choice of graphics, brand vibe, musical influences, skating style and clothing cuts.
ALVIN TANG: I have always believed that fashion has a 20-year cycle and whatever that’s happening right now is almost the same replica of the scene in 1998. There was so much emphasis on street and skate culture in fashion back then as well. Everyone was shooting film, there were tons of new ‘indie’ magazines coming out every few months but (that) died within two years. So I believe we are just going through the cycle of time now.
This article was originally published in the September issue of Esquire Singapore.