Tom Penny – The Wizard of Oxford

When he descended on the U.S. skate scene in 1994, everything changed. With an approach that seamlessly blended technical precision and raw gnarliness, Penny revealed a new way forward – one where difficulty met effortless style. His casual footage around Los Angeles and Southern California quickly became the stuff of legend, inspiring a global shift in how style and progression could coexist.

While others pursued fame and recognition, Penny seemed to drift beyond its reach, preferring a life of movement and anonymity over the glare of the California spotlight. Yet by 1996, he was widely regarded as the best skateboarder in the world – a figure whose effortless command and natural style redefined what was possible on a skateboard, even as he remained untouched by the fame that followed him.

By the late ’90s, Penny’s legend only grew. Stories circulated of him showing up to sessions skating in Timberlands, effortlessly doing tricks most pros couldn’t touch in proper skate shoes. He spent time skating and traveling with Chad Muska, the two pushing each other creatively during one of skateboarding’s most influential eras. Then, just as quickly as he had appeared, Penny vanished – retreating to France in near silence. His sudden disappearance added to the mystery, cementing his status not only as a generational talent but as a figure who lived entirely on his own terms. His disappearance deepened his mystique, cementing him as skateboarding’s most enigmatic figure.

Today, Tom Penny stands as a living legend, recognized by many as one of the greatest – if not the greatest – skateboarders of all time. Decades after first reshaping skateboarding, he continues to skate regularly, his trademark flow and ease still unmistakable. True to his roots, he’s never abandoned his love for baggy clothes and his lifelong infatuation with the Wu-Tang Clan, small but enduring symbols of the era and attitude that shaped his unmistakable identity. Having reunited with éS Footwear, the brand that helped define his early career, Penny remains a powerful link between skateboarding’s past and present. Still seen in St. Victor, the quiet French town that became his refuge for many years, although he mostly rolls through many metropolitan streets in perfectly coordinated outfits – colors and tones effortlessly matched, a reflection of the same natural style and instinctive harmony that defines his skateboarding.

I first met Tom around 1992, before we moved to California along with the rest of the Flip team. It was an exciting time for us. We had both just turned pro for Flip and we spent a good amount of time together when I would come visit in England where Flip was based at the time. Sometimes he would come visit me in Copenhagen and we’d skate the local spots and parks around town. He seemed to love Copenhagen from his very first visit in 93. The free spirited mindset and freedom that our city had to offer in the early nineties was something that seemed to suit him perfectly. I cherished having him there and was proud to know him. Excited for my friends to meet him and witness his greatness, on and off the board, first hand. There was no social media back then, so it was like having a friend with special (skateboard) powers, that no one knew about (yet). You had to see it in person, to understand it.

I loved traveling with Tom! Everywhere we’d go he’d do something impactful. Everyone in his wake was left speechless and in awe of his skateboarding. Myself included. After settling into Southern California with the Flip team, in the summer of 1994, we’d started meeting new people and skating spots that we’d only seen in magazines and videos during our younger days in Europe. Tom never really cared who was around when he was skating. He seemed to just want to do his stuff no matter the occasion, or who was in his presence. If you got to witness him skate, good for you. If you, or any media for that matter, missed it, he couldn’t care less, so when we one day found ourselves at the famous Carlsbad Gap he casually switch frontside flipped the large gap within a couple of tries. No media, no contest, no crowds. Just me, him, and Andy Scott. This was a trick that could’ve landed him the cover of most magazines at the time. Did he care about that? I think not.

Mythical stories seemed to echo and follow him everywhere he went. He was magical on the board and everybody who got to witness it could see it. We’d go on road trips across the U.S. with new crews and friends we’d made and while skating the Jeff Phillips skatepark in Dallas. Tom managed to smash his hand on a trick. We all pretty much knew it was broken, but Tom didn’t seem to care. By the time we made it to Tampa, a thousand miles away, Tom’s hand was gigantic. We called it “elephant paw” and laughed about it. Tom didn’t wanna go to the hospital. I got the feeling he thought it was too much time away from all the fun stuff. So he just kept skating, smoking, drinking, and whatever else we were doing at the time. That’s his philosophy on life, I think. Follow the fun and whatever feels right for him in the moment.

Of course Tom had just about every company in the skateboard industry wanting him to ride for them. One of the companies lucky enough to get Tom’s stamp of approval was éS, one of the biggest shoe companies around, at the time. While traveling on a Canadian demo tour with Sole-Tec (parent company of éS) we quickly noticed a change in culture from the restrictive USA we’d become accustomed to while living in SoCal. Everything in Canada seemed much better. Freer and more open minded, like the Europe and UK he’d let go of just years prior. Kids would give us weed at the demos, drinking age was 18, everyone was nice to us, and the people just seemed happier and more like what we’d been used to growing up. It was America, without the BS! So when the tour ended and it was time to go back to the US, Tom proclaimed that he had “lost” his passport and therefore couldn’t go back to California. The next morning we got a call from the local shop owner telling us that some kids had found Tom’s passport in a trashcan outside a 7/11, near the demo we’d done. To this day I’m certain that Tom threw away his passport on purpose because he didn’t want the fun to end.

By 1998 he’d made a springtime exit from the U.S. to go back to England. I met up with him at Wembley Area in the summer for one of the biggest European skate events of the year. After that, Münster and a random stop in Amsterdam before heading back to Copenhagen. Tom came along, of course, and quickly befriended a group of friends of mine from Christiania we’d met up with in Münster. In Copenhagen it quickly became apparent to me that Tom had no intention of going back to the U.S. anytime soon. Europe seemed to suit him much better. More secluded, fun, and away from the spotlight of magazines and filmers trying to chase him everywhere he went. I left Copenhagen after about 5 weeks in Europe. Tom stayed in Copenhagen and helped build the legendary Wonderland bowl in Christiania with Albert and the crew. That’s the thing about Tom, he likes the small underground scenes and always did. Down for an adventure, but the fun ones.

So if you happen to see Tom in the streets, consider yourself lucky and remind yourself that you are in the presence of a true OG who always stayed true to himself. Blink and he might be gone. You’ve just witnessed a unicorn!

Tom Penny (Favourites)

Favourite Wu-Tang album – Wu-Tang Forever

Favourite Wu-Tang member – RZA

Favourite Wu-Tang track – Reunited

Favourite Tom Penny board graphic – Jim Morrison

Favourite Skateboarder – Tiago Lemos

Favourite English skateboarder – Kyle Wilson

Favourite trick – 360 flip

Favourite clothing item – Polo Bucket Hat

Favourite skate shoe – Es’ Penny 2

Favourite Timberlands – Black Tibs

Favourite dish – Steak and Chips

Favourite colour combo – Red Blue White

Favourite city – Barcelona

Favourite childhood memory – First time in the USA

Favourite skateboard photographer – PAL