This one's a little tricky. I started skating in spring of 6th grade, which immediately led to me hanging with some kinda rough teens and getting busted by the cops for weed at 12 years old that summer ('96). My first pair of skate shoes then were some Airwalk jacked that I got for my birthday.
after that weed bust, some guilt shit kicked in and I kinda regressed back into kiddo status for a while and stopped skating. I picked up a board again at the end of my freshman year('99) and ended up in these bad boys... Globe Gershon:
These are the exact colorway/model of each shoe.
Side note: Those Airwalks would totally fly today, and the Globes are fucking hiking boots.