Since we’re talking about Tim Stoker physical appearance headcanons: Based on vibes I’m going with the headcanon that Tim is a hat guy in a casual environment.

He just seems like the sort of person who’d like wearing baseball caps and beanies. Especially on days when he still wants to look decent but doesn’t feel like messing with his hair.

He thinks it adds a bit of “bad boy charm” to his look, but Sasha, Martin, and Jon all (lovingly) think it just looks like he’s wearing a tacky hat.