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Hensley Sailor Jerry Bundle

HENSLEY SAILOR JERRY TATTOO STREET SWINGER TEE (Size): Small
THE HENSLEY SAILOR JERRY TATTOO STREET SWINGER (Size): 8

A fresh take on a skateboarding classic, the Matt Hensley Sailor Jerry Bundle combines a premium graphic t-shirt with a matching deck featuring Bob Hickman's unique tattoo-inspired interpretation of the legendary Matt Hensley Street Swinger graphic.

Drawing inspiration from traditional Sailor Jerry tattoo artwork, Bob collaborated with a tattoo artist friend to create an authentic homage to early American tattoo culture while preserving the spirit of one of H-Street's most iconic graphics. With additional production work and visual effects by T-Mag, the result is a striking reimagining that bridges skateboarding history and classic tattoo art.

The premium t-shirt is digitally printed in the USA using high-quality inks and apparel for exceptional detail, comfort, and durability. Paired with the matching deck, crafted from premium Hard Rock Maple and printed in California, this bundle showcases a unique artistic vision while paying tribute to Matt Hensley's enduring influence on skateboarding.

Bundle Includes:

  • Matt Hensley Sailor Jerry Street Swinger Deck

  • Matt Hensley Sailor Jerry T-Shirt

A collector-worthy bundle celebrating classic H-Street graphics, traditional tattoo art, and the lasting legacy of Matt Hensley.

Made in the USA.

About Matt Hensley

Matt Hensley started to ride a skateboard in the late 70’s, while all the really great skate parks were still around. His local park was Surf de Earth Skatepark in Vista CA, where many of the legendary San Diego Pro’s, like Doug “Pineapple” Saladino, Dennis Martinez, Shogo Kubo and Dave Andrecht also skated.

During the 80’s, Matt became a household name in the world of skateboarding through his unique approach, style and progressive street skating, in which he and a few other super talented young street riders would change skateboarding forever.

In 2018, Matt got inducted into the Skateboarding Hall of Fame, Matt remains a legend in skateboarding and significant part of H-Street, both past and present.

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