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Skateboarding.

It’s many of our generations’ introduction to streetwear and collecting sneakers. And not only was it at the forefront of many of our now crazed obsessions, but it’s played a pivotal role in how we build our wardrobes and what’s in our footwear rotations today.

An example of the timeless appeal of skate fashion from Supreme.

Despite Supreme being at the height of their existence amongst streetwear connoisseurs of today, they have also played a pivotal role in defining skate style on both coasts since the mid 90s. Rugby polos, box logo tees, bold color blocking, and repurposed workwear essentials were what put them on the map then and they’re what are making them as relevant as ever today.

So relevant in fact that there have been a host of brands to follow suit with this business model to build their own cultural cache.

How does anyone get acquainted with what skate style looks like and what the mainstay building blocks are that create this timeless look? Watch just about any renowned skate video out there and that’s the golden ticket to endless wardrobe inspiration.

The Nike SB Chronicles series, Supreme’s “Blessed” or “Cherry,” adidas’ Away Days, the Illegal Civilization saga, as well as Vans’ Propeller movie. Skateboarding has carved out a lane of its own, not necessarily having to adhere to the cyclical trends in fashion. In other words, what was in way back when is probably still relevant now, but perhaps with a new wrinkle here and there.

Nike SB team members filmed in Chronicles.

The stars of the Illegal Civilization 3 movie.

The History

Nike tennis recreated an iconic photo of James Dean walking the streets of NY with John McEnroe in the 80s. Upon the launch of the Challenge Court SB in 2012, they did it again with Gino Iannucci.

Before skateboarding really hit the mainstream in the late 90s, there was still a major cross-over amongst basketball and tennis silhouettes that were just as applicable for better board feel as they were for grip on the court. Take OG Nike SB team member, Gino Iannucci for example. The NYC native has been renowned for skating icons like John McEnroe’s Challenge Court, due to its ability to promote better support and maximize the feel of the board. In fact, it made so much sense to skate this shoe that Nike SB would incorporate it into their fall/winter collection in 2012.

The 00’s were dominated by boxy fit hoodies, cargo pants, and puffy skate shoes. And while it looks like the chunky runner trend is slowly starting to evolve, it appears that the apparel wave from the early 00’s skate scene could fire again. With cargo pants making a comeback out of nowhere, it appears that designers are enabling the nostalgic nod even further with a more literal approach. Virgil Abloh has certainly incorporated these silhouettes into his collections at Louis Vuitton and OFF-WHITE, while acclaimed skate brands, like Vans and éS are also resurfacing with aesthetics inspired by the iconic era.

OG skate legend, Mike Carroll mixes grunge and skate aesthetics to form a look that's still as relevant as ever. — OG skate legend, Mike Carroll mixes grunge and skate aesthetics to form a look that’s still as relevant as ever.

One of the original four Nike SB team members, Reese Forbes with the Sea Crystal colorway of the SB Dunk High.

This look from Eric Koston would still land him on the front page of any style blog.

Cargo pants and hoodies. A combo that Josh Kalis still incorporates into his wardrobe. And a combo that many streetwear enthusiasts have also begun to adopt.

Long-time Vans rider, Tony Trujillo pairs black skinny jeans with a graphic tee and his signature Dr. T silhouette.

Jonah Hill's Mid 90s movie would establish the look that would transcend through skate culture's image into the mid 00s. — Jonah Hill’s *Mid 90s* movie would establish the look that would transcend through skate culture’s image into the mid 00s.

Skaters That Have Style

Lance Mountain

Button-ups and chinos, like Blazers have plenty of hang-time when it comes to timeless fashion pieces.

Lance Mountain might be one of the more relevant conversations who stem from a skateboarding background. But it’s not just the world of skateboarding where these conversations are taking place. The original Bones Brigade icon and Stussy tribe member is just coming off a successful release of another signature rendition of the Nike SB Blazer. And not only that, he’s responsible for the most popular colorway thus far that launched for the Air Jordan 1 x Nike SB series.

Much like the shoes he skates, Lance Mountain’s style is timeless and simple. Rarely does it stray from button up shirts and chinos, but then again, it doesn’t need to. He’s established a versatile uniform that works just as well five years from now as it did five years ago. And it makes it that much easier to pair with his go-to skate shoes, like SB Blazers and Jordan 1s.

They look just as good from the streets as they do poolside. Lance Mountain skating a signature pair of Blazers.

Want Lance Mountain's smooth skate style? He's a member of the Stussy tribe, so the best bet would be to start at their web shop or any of their chapter stores. — Want Lance Mountain’s smooth skate style? He’s a member of the Stussy tribe, so the best bet would be to start at their web shop or any of their chapter stores.

Gino Iannucci

Gino Iannucci gives style a whole new meaning for skateboarding. Not only does he mix into his NYC roots, but he puts a sportswear flair on his look to create something that’s not only unique, but authentic.

It seems as though skateboarders have an ability to spot the trends first or just make apparel styles look relevant even if they’re not necessary one of the season’s must have items. Gino Iannucci is one of those individuals who represents the motto, “It’s the man the makes the clothes” – pairing easy essentials like tees and chinos with cool Nikes that have an effortless air about them. Like several other prominent skaters, he’s been able to parlay his skate influence and sense of fashion into modeling, appearing for seasonal campaigns, like Eidos.

Skate meets sport influence once again, as Gino wears the Nike SB Lunar Gato, which borrows from Nike's long-standing soccer design influence. — Skate meets sport influence once again, as Gino wears the Nike SB Lunar Gato, which borrows from Nike’s long-standing soccer design influence.

Gino Iannucci models for fashion brand, Eidos.

Paul Rodriguez

One of P-Rod's latest video parts is every bit as relevant in 2002 as it is now. — One of P-Rod’s latest video parts is every bit as relevant in 2002 as it is now.

Paul Rodriguez couldn’t be more on the 00s trend during the actual time period as he is today. While he’s certainly had an array of his own signature shoes that fall under the bulky skate shoe trend with Nike SB’s, that hasn’t stopped him from skating an array of coveted Dunks over the years. Winning his first X-Games competition in the Mexico Dunk colorway, he’s also been spotted skating several grailed SB Dunk x Supreme offerings over the years.

From some of his latest video parts and segments on his YouTube channel, Paul Rodriguez is clearly a fan of the cargo pants and hoodie combo, which has also become the look of quite a few streetwear enthusiasts these days. While they pair easy with puffy skate shoes, P-Rod shows that these essentials can also be paired with a classic pair of SB Dunks. The LA skater’s style hasn’t needed to evolve much over the years. In fact, his casual loose fitting chinos and longer black tee pairings from his Nike SB It was a Good Day video are as relevant as ever.

It was a Good Day Easter Eggs:

Eric Koston makes his debut appearance as an official Nike SB member
Kobe Bryant makes an appearance
Paul Rodriguez is actually wearing a suede iteration of the P-Rod 3 when he Tre-Flips the stairs because it’s easier to skate for him than the traditional leather offering
The cop in the passenger seat of the squad car is played by Lance Mountain
SB riders, Shane O’Neill and Theotis Beasley also make cameos. Theotis Beasley is wearing the SB Dunk Low “Asparagus”
Ice Cube runs over P-Rod’s board in the lowrider

Eric Koston

Koston's kit works just as well with your Dunks as it does with your Kostons. — Koston’s kit works just as well with your Dunks as it does with your Kostons.

Eric Koston is regarded by many as the greatest skateboarder of all time. His blend of technicality and novelty not only translates to skateboarding, but also to fashion. While his wardrobe may seem impossibly simple, that’s probably because it is.

However, each of his outfit’s versatility and simplicity goes with almost every Nike SB silhouette an array of Nike Sportswear and performance offerings as well. While he’s co-founded several of his own apparel brand’s, it’s no secret that Frosty is in fact, no stranger to Supreme. Wearing the brand almost as long as he’s been pro, Koston has an ability to give each grailed Supreme essential its own newfound appeal, by merging his signature skate style and affinity for Nikes.

Cropped trousers are having a moment in menswear right now, but they've always been relevant in skateboarding. — Cropped trousers are having a moment in menswear right now, but they’ve always been relevant in skateboarding.

Flip the script and try something new. Flannels wouldn't normally thought to be paired with sweats and Koston SBs, but Frosty makes it something novel to try. — Flip the script and try something new. Flannels wouldn’t normally thought to be paired with sweats and Koston SBs, but Frosty makes it something novel to try.

Eric Boston blends early 00s inspiration with workwear essentials, like his painter pants, which have also transcended into skate culture for years.

Jimmy Gorecki

You've already got the cap and kicks. Now you just need to get your hands on a pair of JSP sweats. — You’ve already got the cap and kicks. Now you just need to get your hands on a pair of JSP sweats.

Jimmy Gorecki might not be the most obvious name that comes to mind when you think of skateboarders from the 00’s, but if you know the labels, Ice Cream, JSP, and Standard Issue Tees, you’ll understand why he’s on the list.

As one of the original member’s of Pharell’s Ice Cream skate team, Jimmy Gorecki is at the forefront when it comes to uniting both skate and streetwear silhouettes. Inspired by the minds of skateboarders before him, like Josh Kalis and Pete Eldridge, Jimmy is also known for two other style related ideas – skating in sweatpants and Jordan 4s. He’s even got his own sweats label, JSP (Jimmy Sweat Pants that he recently revived, which produces an assortment of beyond basic sweatpant designs and colorways. While the Philly native is certainly known for skating Jordan 4s, he’s no stranger to the puffy skate shoe classics, like Josh Kalis’ signature DC silhouette.

Forever a reason to skate Military Blue Jordan 4s.

Suprem sweats, No. One Bravos, and Standard Issue tee.

Jimmy Gorecki along with the rest of the original Ice Cream/Billionaire Boys Club team.

Tony Trujillo

Oversized flannels, graphic tees, and wide-legged chinos are skate style building blocks.

Tony Trujillo is California skate style to a T. Grungy flannels, slightly oversized trousers, graphic tees, and his own signature Vans that draw inspiration from the Vans Old Skool, TNT is the definition of skate style.

These past few seasons, designers of all sorts have been sliding over the lightweight hoodie to make room for long-sleeve tees with graphic prints – a move Trujillo knows best. He also further personalizes his style by wearing mismatched colors of shoes like the Sk8-Hi and even his own signature shoe to make his style his own.

Pioneer of mismatched coordination.

Tony Trujillo skating his Vans TNT Advanced Prototype.

Josh Kalis

The look consumers wanted then and what they still want now.

Josh Kalis has been a signature DC athlete for quite some time now and it’s not only his skate style that stands out on all the magazine covers he’s been featured on, it’s also his wardrobe style.

For many that grew up reading Thrasher or Transworld Skateboarding, it’s probably Josh Kalis that’s responsible on some level for helping build their own style. New Era Yankees caps, cargo pants, and the DC Josh Kalis 1. That was the look and went beyond feeling good on a skateboard.

Classic skate style from the early 00s.

The reason that people still want to skate puffy skate shoes and baggy sweats today.

Blondey McCoy

Blondey McCoy is another pro skateboarder turned model turned entrepreneur. He’s also the founder of the apparel label, Thames, which houses an assortment of elegant knits, jackets, and premium basics with eclectic color palettes and logos. His brand has even collaborated with fellow, English label, Fred Perry.

Beyond skateboarding, Blondey McCoy certainly has his own skate style, but it’s probably more fashionably curated than many of his predecessors. He’s been featured in several campaigns for Palace, Valentino, Burberry, and even adidas since he is on the team’s skateboarding roster. The 21-year old’s style is polarizing between what he wears while skateboarding and going out. Shorts and a tee with a pair of adidas might suffice for skating, but during the evening hours, his style might call for a button-up shirt, a cardigan, and a pair of loafers.

While Blondey McCoy might consider himself Generation Z, his personal style is wise beyond his years, being fond of knitwear from the likes of Supreme and Fred Perry, but mixing it up by throwing in a pair of adidas track pants. He’s also fascinated by the cross-over between skate and designer fashion, which is a move that’s only become more accepted in skateboarding – especially since the mid 00s.

Blondey McCoy celebrating his Thames x Fred Perry collection.

Blondey McCoy's wardrobe houses a palace of Palace goods. — Blondey McCoy’s wardrobe houses a palace of Palace goods.

Subtle sophistication with a hint of streetwear.

Bloody McCoy has appeared in a wide genre of brand campaigns, including Burberry.

Blondey McCoy models for the adidas and Palace collection.

Hailing from London, Blondey McCoy makes it known with the way he dresses, incorporating plaid pants, trench coats, and adidas trainers of course.

Olan Prennatt

Would you do this to your Jordan 4s? Olan Pregnant makes a pretty good point for why it works. — Would you do this to your Jordan 4s? Olan Prenatt makes a pretty good point for why it works.

Olan Prenatt is one of those household names that’s been prominent in skateboarding since his youth. A prodigy in the making, Prenatt has appeared in the film, Mid 90s, been featured in Fear of God’s ESSENTIALS campaign, and most recently modeled Rhude’s V1 Low sneaker. All of that aside, he’s got his own style. And it’s really good. Similar to Jimmy Gorecki, Prennatt skates a lot of coveted basketball sneakers, like Jordan 4s, 5s, 6s, and even 10s. Conventional? Not necessarily, but he makes a good case from a style perspective.

He’s also making it appealing to skate sweats and make it look like skateboarding was supposed to be done that way. The majority of his wardrobe building blocks are skinny jeans, graphic print sweatshirts, and loose fitting flannels. Pretty much anything that’s California cool.

You've seen the look in streetwear, but how about in skateboarding? — You’ve seen the look in streetwear, but how about in skateboarding?

Olan Prenatt always has some vibrant colors to go with his kit.

Olan Prennatt mimics Jay Adams' signature Dogtown skate style. — Olan Prenatt mimics Jay Adams’ signature Dogtown skate style.

Olan Prennatt skating the Richard Mulder Nike SB Dunk High. — Olan Prenatt skating the Richard Mulder Nike SB Dunk High.

Kevin Bradley

Better when they're beat. — Better when they’re beat.

Kevin Bradley has become a relevant talking point over the past few seasons. Mostly because of his signature Nike SB Dunk High and Delta Force silhouettes, which reveal either red or blue shades after rigorous skate sessions.

Aside from having a couple signature colorways with the SB division, Bradley has also accrued a timeless skate style over the years. While Supreme box logo tees and SB Dunks are just as relevant ten years ago as they are today, he also throws in a few variables by incorporating cargo pants, striped tees, and even long-sleeve polos into his kit. Simply put, his style is just as throwback as it is modern.