All Vans on deck: Skater fashion from the ’90s to 2019

Photo by Belle White, Photo Editor. Design by Austin Clay Willis, Design Director.

In its early days, skateboarding was the sport of outcasts. If skaters weren’t ripping up the empty pool in your backyard, they were probably already in the backseat of a cop car.

Now, though, it’s not so uncommon to see anyone from a 12-year-old girl to a 40-year-old hipster sporting a pair of Vans, an oversized Polar Skate Co. hoodie, or a Dime beanie.

Skate style has changed just as skate culture has. From the legalization of skateboarding in the streets of downtown Victoria to the announcement that skateboarding will be an officially-recognized sport in the 2020 Olympics in Japan, it’s been almost 30 years since skateboarding’s rise to popularity in the 1990s — and what a ride it’s been.

But with the shift to online shopping that the world has seen in the last decade, some traditional skate shops have seen smaller returns. This isn’t just about profit — brick and mortar skate shops can be the heart of a skate community.

In All Vans on deck, we took a look at what’s changed — both good and bad — in the skate fashion industry and beyond.



Drew Summersides, who rides for leading brands like Emerica, Toy Machine, and RVCA out of Vancouver, took us for a cruise down memory lane.

“Skating in the ’90s was a lot different. [Skaters] were a lot more fucking punk and they wouldn’t take shit. They would break your car windows and do whatever they wanted.”

Being on the periphery, skaters from the ’90s — and before — had a hard time becoming accepted into normal society — not that many of them wanted that, anyway.

Shane Johnsen, founder and owner of Tribute Boardshop in Nelson, B.C., also remembers the ’90s skate scene.

“Back then skateboarding just had this [reputation]. We were all smoking cigarettes and we had dreadlocks and we had this and we had that,” says Johnsen. “There was always something that put you on the fringe, therefore too many people didn’t understand it.”

“Skate fashion has just become normal fashion. It’s just how people want to dress all the time now which I think is really cool.”

While being on the margins once kept skateboarding from the mainstream, it’s fringe culture is now one of the reasons that it draws the masses — a contradiction if there ever was one.

“It’s one of those few fringe things left,” says Johnsen. “And that’s why mainstream media gravitates to it now — because they’re always trying to grab at something new, something … different.”

Alanna Ward. Provided photo by Lauren McRae.


And as skating’s continued to rise in popularity, it’s had an impact on people’s perceptions, says Summersides.

“There’s no real stopping it so it’s either get with it or get out. There’s no choice. Like skating’s going to be in the Olympics now. It’s just a normal thing,” he says.

The normalization of skateboarding is what made it so easy for Alanna Ward, a fourth-year Psychology major at UVic, to start hitting the ramps.  

While the window-smashing youths of the ’90s might have made the skater community difficult to approach, Ward says the dynamic today is different.

It’s nice because everybody’s so welcoming, ’cause everybody kinda knows they all started somewhere,” says Ward.

Ward observes that just as skateboarding has become more accessible, so has the clothing.

“Skate fashion has just become normal fashion. It’s just how people want to dress all the time now which I think is really cool.”



Skate fashion is constantly entering new life stages.

“When I skated, it was kind of like Dead Kennedys, SNFU, punk, you know?” says Lee Miller, a Sales Associate at Oak Bay Bicycles. Now, you’re a lot more likely to see skaters in nice-fitting jeans and a plain tee, he says.  

Back when Miller still took to the ramps, everyone wore black tee shirts, baggy shorts, and oversized hoodies.

“Even going back farther, a lot of people wore neon and stuff like that,” he remembers.

Though Summersides missed the neon era, he’s rocked the fashion trajectory all the way through its baggy-to-tight transition.

“I remember wanting the biggest shoes and the sickest boot-cut jeans, like where it just hung over your shoes and looked so good,” he says. “And then the pants got tighter and tighter, and then we started wearing leather jackets and jean jackets and wearing mascara.”

Provided photo by Jacob Huff, Photo Contributor.

Soon, this shift to tighter clothing styles drew attention from the high fashion world.

“[Dylan Rieder] was the first to bring [skate style] to the runway,” says Johnsen. Rieder was known for his slim jeans and tucked-in tees. He passed away in 2016 at 28 years old.

In his early twenties, Rieder, a prominent professional skateboarder, started modeling for major brands like DKNY, and brought skate culture into high fashion outlets like Vogue in 2013.

But the baggy clothes of the past are set to make a comeback, says Summersides.

“I think [skate fashion] always goes through phases. It kind of does 15-year turnarounds … You are starting to see big bulky shoes … and super baggy jeans [come back],” he says.

Johnsen agrees that skate style is cyclical. In the fashion world, things that went out of style decades ago can often be revived.

Take skate brand New Deal Skateboards for instance.

New Deal was founded in 1990 by Paul Schmitt, Andy Howell, and Steve Douglas in response to the rise in popularity of street-skateboarding culture.

“[New Deal] was a brand that didn’t even last super long because, like so many things that are super cool, they become a flash in the pan and they’re gone as fast as they were around,” says Johnsen.

But now, New Deal is back.

“[New Deal] fashion is what we’re seeing a lot of right now,” Johnsen says. “That’s what I’m seeing big time. There’s a little bit of old school, New Deal street skating from the early ’90s, mixed with Seattle grunge.”

Summersides says skate fashion is always looking for new niches.

“People want to be like people who are just enjoying themselves, being themselves, on their own fucking tip.”

“It goes in circles because it gets saturated … and then you want to be new and exciting but there’s no real newness,” he says.

To get ahead in the style game, Summersides looks for that next new trend by studying the skateboarding legends.

“You always look back,” he says. “People are paying homage, almost, to the trailblazers of the ’90s and the 80s… They watch all their [skate] video parts and they get super hyped on them, and then they start embodying those people.”

But the trailblazers of skate fashion aren’t too concerned about setting fashion trends, says Summersides. “They’re just out there killing it, doing their own thing.”

“People want to be like people who are just enjoying themselves, being themselves, on their own fucking tip,” he says.

Johnsen emphasizes the role of 20-something skaters when it comes to the rise of skate-fashion trends.

“That’s when you’re really leading it because you’re not overthinking anything, you’re just making rad shit happen, or designing rad shit,” he says. “When Dylan Rieder was at his peak … he was 22.”

Johnsen, a self-proclaimed old timer, says today’s skate fashion trends are beyond comprehension. As a shop owner, he is forced to look to the young ones to keep up.

“I don’t get it. I just can’t get into the giant baggy pants … I really have to rely on those [younger] guys now, too, and … start trusting them [with fashion choices].”



While young people are blazing the skater style trail, Johnsen worries that they could also be the demise of the skateboarding scene because so many buy their gear online. Without brick and mortar skate shops, the skate community just isn’t as strong.

“The scary thing now is everything’s so accessible online,” he says. “We see a percentage of those young people who don’t understand what a core shop does for a community. They just put their dollars into Amazon, Amazon, Amazon, and then that [money] leaves town.”  

This puts local shops and smaller skate brands at a disadvantage because they can’t compete with the larger companies in the online market, says Johnsen.

“I just know [skate shops] can out service the internet, but sometimes I don’t know that that young, young generation cares at all.”

He also points out that the big corporations are co-opting skate fashion for profit.

“Palace skateboards, for example, was started with Adidas money,” he says. “It’s big, people were stoked on it. But nobody fucking knew it was Adidas’ money for the longest time.”

Johnsen hopes current and future skateboarders will continue to support the scene because the people who run the skate shops help push for new skateparks and support the skate community.

“I just know [skate shops] can out service the internet, but sometimes I don’t know that that young, young generation cares at all.”



The unfortunate reality is that Amazon is often the cheapest option in what has become an expensive industry.

Ward feels skateboarding’s shift from grunge to more sanitized street fashion has had the side effect of raising the prices you now see at skate shops.

Summersides agrees, adding that skateboard gear doesn’t have a long lifespan either. Skate shoes, for instance, get eaten by skateboard grip tape, which is like sandpaper. And they’re quite expensive, especially if you skate a lot.

“You go through a pair in a month. $100 a month on shoes is kind of shitty, especially for a kid when you’re growing up. That’s what I remember at least, just my parents always being pissed about buying new shoes,” says Summersides.

While Summersides could usually talk his parents into buying him his next pair of shoes, he had to get a paper route to afford new skate decks, which would last only a few weeks before breaking.

For many, supporting the skate-scene by purchasing from skate shops just isn’t financially feasible.



Dressing like a skater when you don’t actually skateboard has long been one of skateboarding’s deadly sins.

“Fashion is in the eye of the beholder, but don’t just wear something because you saw someone else wear it,” says Ryan Siemens, a skateboarder from Abbotsford, B.C. who skates for the likes of Boardroom, Element Canada, and Vans.

If you steal the looks, you run the risk of being called a ‘poser’.

Johnsen says he skated in the heyday of poser persecution.

“When I grew up it was a real thing. If I saw somebody with a Skull Skates hoodie on [and] I knew they didn’t skate, that got to me, that bothered me. And that’s where [the term] poser came from,” says Johnsen, adding that he doesn’t subscribe to that mentality anymore.

Siemens, meanwhile, doesn’t care too much about non-skaters co-opting skate fashion either. In his mind, it comes down to people not thinking for themselves.

“Just sheep following the latest trends. [They] think it’s cool because they saw their favourite artist wear it, while not knowing what it is at all,” he says. “It’s good and bad; good because people are a little more accepting of skateboarders, but bad because the whole thing about skating is having your own style but now you just look like everyone else.”

Nowadays, it’s almost impossible to tell who skates and who doesn’t — unless they’ve got their board, of course.

“[Skaters are] just blending in now, which is super exciting,” says Miller, adding that this has helped to destigmatize skateboarders.

If you steal the looks, you run the risk of being called a ‘poser’.

It isn’t always obvious that the clothes are designed for skateboarders, he says. The solid colours and lack of skull designs have made current skate clothing more fashion-forward.

Ward says that many of her friends choose to wear skate fashion even though they don’t skate.

“I feel like it gives them a better appreciation of the sport,” she says.

She hasn’t heard anyone complaining about posers, but they do comment on non-skateboarders wearing certain skate brands.

“Definitely with brand names … like Thrasher, where it’s very much like, ‘This is a skate brand’, people do comment on that,” says Ward. “They’re like, ‘Oh you’re wearing a Thrasher hoodie, but you don’t skate … OK’. I don’t even wear Thrasher hoodies because I’m not good enough!”

However, when it comes down to the styles themselves, no one can say they belong to skateboarding, she says. “There’s no label on it.”



With the line between skateboarders and non-skateboarders blurring due in large part to fashion, the public’s opinion of skateboarding — and even skateboarding laws — are changing.

People no longer assume that skaters are just “druggies,” says Ward.

“Before I started skateboarding, it didn’t have that much of a negative connotation to me, but I definitely was like, ‘Oh, the skate park isn’t the best place to hang out’,” she says.

But it’s not like that in Victoria, says Ward. “I’ve come to realize that [there are] actually so many really, really talented skateboarders that are also really passionate about school or are working really hard to forward their careers and stuff.”

Skateboarding only became legal on the streets of Victoria in 2016 after Victoria City Councillor Jeremy Loveday moved to legalize skateboarding downtown. The City of Victoria acknowledged that the number of people for whom skateboarding is a mode of transportation is constantly growing.

Skaters take to the ramps at Rifflandia. Photo by Belle White, Photo Editor.

“One big factor for the changing view of skateboarding is that many old school skateboarders are now middle-aged, tax-paying residents, and some are in positions of influence,” says Loveday.

“Most people have now known someone who has skateboarded, whether that be their child, their co-worker, or their friend. It’s a lot harder to discriminate and criminalize a group of people once you get to know each other.”

Loveday’s motion passed and the City of Victoria changed the Streets and Traffic Bylaw, allowing skateboarding on downtown streets — but not on sidewalks.

Despite the promising step forward, Loveday doesn’t take all the credit.

“It’s also important to recognize all the skateboarders who’ve worked hard to organize, build awareness, and breed understanding. This skateboarder activism led to the building of the Vic West Skateboard Park which gave skateboarders a place to go and helped create understanding and acceptance.”

Loveday feels that skate culture, and the city of Victoria, have changed.

Whether you see skateboarding as a sport, a way to get around, or a source of fashion inspiration, the history of the skate world must be acknowledged.

“The city has shifted demographically and loosened up a bit. Victoria now wants to see itself as a fun, inclusive, city on the leading edge,” he says. “Concurrently, skate culture has shifted. Skateboarding started as a rebel subculture — and for some people it still is — [but] skateboarding is now also a professional sport and a legitimate mode of active transportation.”

The police on Vancouver Island aren’t as worried about skateboarders anymore either.

“Whether someone is a skateboarder or not is of no interest to us, nor is the way they dress,” says Ray Bernoties, Deputy Chief of the Oak Bay Police Department. “We’re not the ‘fashion police’.”

While skateboarding is still illegal on the streets of cities like Nelson, B.C. where Johnsen’s skate shop is located, Victoria has taken positive steps forward in accepting the skate community.

“Anything to get people out of cars and using people-powered transportation options is in my good books and is something [Victoria] should support,” says Loveday.

Whether you see skateboarding as a sport, a way to get around, or a source of fashion inspiration, the history of the skate world must be acknowledged.

A culture that was once condemned for chipping storefront ledges and making powerslide marks on fresh pavement has now blossomed into something that is enjoyed by diverse facets of society.

So the next time you can’t decide what to wear, try observing the skateboarder bombing down your street. Heck, maybe even ask them what local skate shop you should support. Just maybe think twice before picking up a Thrasher tee shirt on Amazon.