I agree with Mike C. abou the first look, but I don't like the second look either. I find the outfit undersaturated in color, and lacking in visual interest. Either they have to throw in more contrasting colors or a clashing color in there (the orange/red sweater is not striking enough to really be the accent piece), or it needs a pattern. I would for both.
Substitute a chocolate sportcoat with a windowpane pattern, and switch out the sweater with a burnt orange one, and you get a much better (and more seasonal) look, imo.
I personally don't like chinos - have worn jeans since HS, and plan to keep doing so, but I would wear a pair of surplus pants.