Damn, these kicks bring back some memories! Right around 1989 - 1990, young buck skate rats (yes, that’s what we used to be called) like yours truly were watching such videos as Shackle Me Not, Hokus Pokus, and Ban This. We were rockin’ baggy Levi’s, SMA or Bones Brigade t-shirts, and any brand of skate kicks. From Vision Street Wear and their rubber ollie tab, to some chunky ass Airwalks, to Air Jordans, the kicks you skated in were as important as who learned to ollie over trash cans first (that was my dudes Jack and Jason; I came third). You had some funny trends, like shoe goo, duct taping your ollie holes, and sawing off your high tops into mids (true speak, where do you think Half Cabs came from?), but that was all part of the creative swagger that skateboarding engendered.

One of my favorite skate shoes was the Caballero. It was comfy, the soles gripped like crazy, and they looked fresh in either shorts or jeans. Some time ago, Van had posted the above Black on Black Caballeros as well as the Gray pair. To complete the trio, we are now blessed with the news that a third pair in the above Tawny Port Red will release alongside these two others on August 21st. Check your local Vans Vault spot closer to the release date.

Images via Crooked Tongues.