Though Sarah of a few years ago would be very surprised to hear it, I am loving the jogger trend. They are a fun substitute for denim in the classic jeans + tee shirt combination. Much like a good pair of jeans, they can be dressed up or down, but the silhouette is fresher, and a bit unexpected (which is apparently my word of the week).
Snakeprint tee: Mynt 1792
Ankle strap flats: BCBGeneration (similar)