Skating In Timbs AKA The Tom Penny Effect

A story that merits more myth than truth – the idea of skating in Timbs, let alone anything other than a flat sole and suede upper seems is preposterous. Strangely enough, it’s being done more and more – at times, as a preference.

In the last couple of months, it’s been hard for us to ignore this development as more participants have begun skating in these unorthodox skate shoes (because, lets admit it, anything is a skate shoe these days). The Tom Penny effect, as we’ve dubbed it, is taking over. And while we’re fully aware that Mackenzie from TWS actually mythbuster’d it by confirming it was actually a Columbia Hiking boot, we’re still going to coincide skating in Timberlands to Tom Penny ;).

Whether skateboarder’s have become uninterested in today’s offerings or have simply gotten so good at skateboarding where they themselves need to make it more challenging, tricks are being done – impressive ones at that. Regardless of their choice in footwear, we’d still be impressed (actually maybe not), but the fact that they’re doing anything more than a kickflip in these massive boots is beyond our comprehension. Btw, to our standards, this is the best trick you’ll ever see in Timbs.

Could this all be one big ploy for Timberland to be in the skate footwear game? Highly doubtful, but we won’t discount the fact that many of these models do look reasonably skate-able. Plus, they’re all cupsoles. Did Timberland just pull a fast one on the skate shoe industry and come out with a cupsole slip-on before everyone else? Damn…

One of the most prolific characters within the TP Effect is Gregory Stewart, otherwise known as @Gregsie. Typically seen rocking a NBA jersey or cut off sleeve tee’s, his outfit isn’t complete without his camo cargo’s and, of course, some bulky boots to skate in. If you spend more than 5 mins going through his instagram, you’ll find an array of skaters from AU, but also clips of Gregsie doing what he does best. To make matters even more confusing, he can skate street in them as well.

Sam Buxton, back smithing a legit rail in some not so legit skate shoes. Photo - Billy Childress

Sam Buxton, back smithing a legit rail in some not so legit skate shoes. Photo – Billy Childress

As distant brothers of the same selection in footwear, the US also has their own Gregsie. His name is Sam Buxton and if you recognize the name, it’s because you watched his “Down Right Evil” part from not too long ago with other prominent figures from the ATL scene. Just from this video part alone, you can easily tell that he’s one of the few people who is just naturally talented on a skateboard – every trick seems to be done with uncanny ease and comfortability. After sharing this line of Sam, it’s come to our attention that the guy has done some myth-worthy things in Timbs. Back smithing any rail is by all means applaudable, but doing it at a legit street spot and in Timberland boots is something that’s completely unbelievable.

Shoutout to those who skated in boots just to do it back in the day. We’re talking about Pepe Martinez, Drake Jones, Kyle James, Brian Wenning and other character’s who made the impossible possible.

If you haven’t had enough of reading up on people who have skated in boots, here’s a more extensive version.


  1. Mark

    November 4, 2015 10:02am

    There’s are cupsole Timberland boots. He could skate even better with those.

  2. somefucker

    February 5, 2016 3:44am

    stunts in his natural habitat

  3. Tom

    December 16, 2017 5:45pm

    They weren’t Timberlands Penny skated in they were Columbia hiking boots. Ffs this knowledge is so easy to come by.


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