Sometimes I like being challenged a bit by how something looks. Personal style can be a bit like perfume, better and much more memorable when there's one note of discord. The message I get from this is something like "I am athletic, modern, and urbane, but also polished and organized". The cut of the top, the too-long dress, the sneakers, all feel intentional despite not following the "rules". If I have one complaint, maybe it's the hair, a missed opportunity for something sleeker.