S2E18: Dressed in Black
Toby first wears a brown open flannel over a tee, with baggy khakis. Then he wears a grey long sleeve with a horizontal chest stripe, and jeans. Still rockin the middle-parted hair. And finally, the baggy silouette lives on with another long sleeve and jeans. And his little B-plot is that he buys condoms just-in-case for Kendra and somehow gets off scot-free.