Wow, some of those must be pretty early pictures. I just have trouble picturing Tyll any different from his current appearance, since I didn't really become aware of him until sometime in 2010.
Funny thing is I went through a Hawaiian shirt phase in 8th and 9th grade, complete with Ray-Bans perched on top of my head. People at school thought I was a little ridiculous, but I didn't care. In the end I think they thought it was cool just because I was so confident about it. Being 70 lbs lighter back then, sadly none of those shirts would fit me anymore, so I couldn't revive that period. But whenever I see a modern-day picture of Tyll I'm reminded of a younger me.
He has much better headphones than I did then, though. He also has better headphones than I do now, but I like to think the delta has decreased since back then.