Evan Mock told us in an interview last year “Skate culture kind of controls every culture. If you think about cool kids, every cool kid is a fucking skater and looks good.” And while that might seem like an exaggeration, it’s kinda true.

Since the turn of the decade, skating and fashion have become intertwined, the sport is responsible for the biggest brands on the scene (Supreme, Palace, Stüssy), the most hyped sneakers (Nike Dunk SB), and its biggest figureheads (Blondey McCoy, Lucien Clarke, Jason Dill, to name just a few).

In fact, the sport arguably birthed streetwear. Hiroshi Fujiwara, who is often cited as the godfather of streetwear, has said that 90s skate label Vision is the first streetwear brand that caught his attention, going on to say in an interview, “the street fashion I envision comes from skateboarding. Skateboarding was a sport you did on the street, so I think that’s where it comes from, originally.”

As streetwear has enjoyed its rise from underground to becoming a defining force in contemporary style, skating has joined it and been embraced by high fashion on the way. What started out as a hobby enjoyed by Californian surfers in the 50s has transformed into a subculture so deeply intertwined with contemporary style that Louis Vuitton has a signature skate shoe, which not only looks like the chunky DC sneakers of the 90s but skates just as well, if not better than them.

Even the brands with deep ties to the culture have bits of formalwear sprinkled into their graphic streetwear collections: Fucking Awesome has the most incredible selection of cardigans, Thames makes ties, and Pop Trading Company’s new purple suit sits somewhere in-between Pitti Uomo street style and skate-appropriate workwear.

This slightly confuses the question of “what does skater style dress mean?” The baggy jeans and oversized T-shirts of the 90s are the first images that come to mind, but skating has come to encompass a plethora of style tribes.

Below, we’ve gathered some of our favorite skaters, from the OG’s to the new wave, who prove that skaters innately have impeccable style.

Scroll down to see some of skateboarding’s best-dressed figures

Jason Dill

A skateboarding legend, Jason Dill has pushed into increasingly stylish territory since he burst onto the skate scene in the 90s. The California native runs the label Fucking Awesome, works with Supreme, and has his own signature adidas skate shoe.

One of the OGs who has countless looks to take inspiration from, the recent outfit above is a personal favorite.

Lucien Clarke

What happens when you pair a London-based skateboarding brand established in 2009 and a French luxury fashion house founded in 1854? The outfit above.

Lucien Clarke told us in 2009 that “I’d like to think skateboarding and fashion is one entity. I’ve never seen it as separate worlds. It depends how deep you go into it,” so it’s no surprise he’s clutching a board with one hand while rocking LV loafers on foot in the look above.

Tom Penny

While the other skaters on this list have been instrumental in developing fashion’s ties with the sport, Tomy Penny is not one of them. The skating legend who modernized what street skating is today has an apparent apathy for trends and that’s whats landed him here.

His uniform of baggy jeans, oversized polo shirts, and his iconic black beanie has remained largely unchanged since the 90s and is an authentic snapshot of how the sports OG’s have influenced the new wave.

Evan Mock

Skater, model, and actor Evan Mock has proven that he’s not one to be boxed in and his style reflects that. With his signature died hair, you’ll catch Mock skating around fashion week and entering shows clutching his board while wearing fits that combine the culture’s fashion history with his own experimentation, like the outfit above.

Myles De Courcy

Featured in our recent editorial with Celine, Myles De Courcy is part of the new wave of skaters who rekindled their love of skateboarding during the COVID-19 pandemic. Pushing for a more inclusive skate culture, their style mixes androgynous elements such as crop tops and skirts with classic 90-inspired skatewear.

Blondey McCoy

As we wrote in issue 19 of Highsnobiety magazine, “no skater has represensented this mixture of glamour and grit quite like Blondey McCoy.” Another Palace alumni, McCoy’s style sits somewhere between British heritage wear and workwear-infused skate style.

Whether it be through his label Thames, various art projects, or modelling for the likes of Burbery, his creative streak has gained him fans far beyond skating.

Dylan Rieder

When speaking about skateboarding’s collision with high fashion, the late Dylan Rieder has to be part of the conversation.

Going pro at the age of 18, he bagged himself a place alongside A$AP Rocky in Vogue’s “untamed Youth” feature back in 2013 and his work as a model only tied him closer to high fashion. But most important was his personal style, comprised of slicked-back hair, slim black jeans and a white vest or t-shirt, he looked more like a filmstar than your stereotypical baggy-clothed skater.

Boo Johnson

Whether it be graphic skatewear, gorp gear, or dress shoes and a shirt, Boo Johnson seems to be able to make anything look good and it’s landed I’m a second job as a model.

The tattoo-covered California native skates for DGK while also running his brand and regularly releasing clothing collaborations, all under the guidance of his manta of “Just Having Fun.”

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