Using all the research skills that TotD has at his disposal (got halfway through a Google search, page froze, said “fuck it,”) this photo can now be definitively (not in the slightest) proven (again: nope) to be the earliest sighting of Snake T-shirt.
This shot is reportedly from one of the Oxford Plains, ME, shows in 1988. Bobby has paired Snake T-shirt with his usual short shorts and a pair of Ugg boots. (Bobby had been warned on numerous occasions not to use the Time Sheath technology to go shoe shopping, but he countered by saying that they were “sooooooo totes comfy” and that everyone was just “jelly” and “haters” and then he went to Starbucks for a latte.)
Mickey is a lifeguard.