My first thought was… why does he appear to me to be so quintessentially French? Is it what he’s wearing, or,the way he’s wearing it? My next thought was … the lady beside him seems more interesting. I’d like to see her complete outfit. As RJH said, the monochromatic look seems pretty slick.
The ‘first day at school’ sentiment seems right to me. But I think the problem are the shoes: they are too heavy and worn in and the black colour does not go well with the rest of the outfit. Their shape and style remind me of the functional, durable shoes boys get to wear to school day in day out.