This is probably one of the coolest tees I own, but I can't take any credit for it. My friend, Lindsey, found this gem while concept shopping and I became obsessed with it. It's cooler than I'll ever be, but probably not as cool as Linds.
Zara Tee (unfortunately a lot of people thought this tee was awesome because it's sold out online).
J Brand Skinnies
WHO.A.U military trench (stores only)
Bull Boxer boots (DSW stores)