What I enjoy most about these pieces are their playful yet cool qualities. This boot by Acne, the Zweig, is the kind of piece that generates double takes. Many times, a hybrid idea such as this can lose it's charm, but these boots retain style in addition to the utilitarian component (they also come in dark brown).
The shirt by Shake Appeal, as part of their Autumn/Winter 2012 collection, says it all; it's a geeky-cheeky. I'm digging the overall look as well.
Shake Appeal source: FuckingYoung!