I really like this shirt/jacket by Post Overalls. The Cruzer shirt could be worn as a single layer or as a lightweight jacket. I heard from a little birdy that girls like to steal their boyfriends' jackets and blazers to wear as oversized looks. If your girl stole this from your closet I bet all the hipsters in the world would hit on her...It's on sale at superdenim.
Chambray is a popular guy lately. This waistcoat by Kato is really nice. Plus, girls like guys who wear three piece suits and what not. Rock this over a nice white oxford and a good pair of chinos or denim- we can't all wear three piece suits around everywhere. Again, on sale at superdenim.
Of course I'm going to put the new standards on here. The color is dark enough to work with a chambray shirt (or vest) without looking too much like a texas tuxedo (or canadian tuxedo depending on which one you're closer to). Get them at the h(y)r store.
These Fracap mountaineering boots are awesome. Everybody's on the Red Wing tip, but for me, these would be the boots I'd buy. Get them at Oki-ni quick.