This cover of Poweredge from May 1989 is one of my favorites. I've never heard anybody mention it before but this cover photo was from January 1989 when he still rode for Powell Peralta. But when this issue came out he had already started riding for World Industries and got a new wheel sponsor, Santa Cruz, and rode OJ II Teamriders.
A lot of people relate this photo to the Speed Freaks video because it was taken at the same place he skates in it. I don't know what Airwalk had to say about it but he was definitely wearing Chuck Taylor's in the video. You have to dig the Morrissey shirt.