I photographed YouTube phenomenon, comedian Bo Burnham, a few weeks ago for the Boston Globe Magazine. Bo had just gotten back from a comedy festival in Australia and had to be a bit jet-lagged for the shoot, but none of us knew it. He really got into character and was fearless, as some actors can do, really getting into the characters . He turned out to be very funny and was very up for the idea of dressing up as high school archetypes. He didn't even mind wearing the singlet for the wrestler character or the grey lipstick for the goth.
In setting up the shoot, we didn't quite realize how tall he was, and the pants for the band uniform character were quite short. That turned out to be serendipitous, because the length (or lack of) really worked for the character. What says "high school awkwardness" more than too short pants?