I think the shorts look realistic enough. Remember ...... shorts in those days werent shorts like today .... they were big and baggy. Also exact sizes were not common place, and could also have been hand-me-downs from a bigger brother or father!
I think the dio is shaping up well, and with the addition of the toplayer of resin with some wake... it should be brilliant.
One thing that could be improved is where the little pier starts. Either the ground would fill up to the pier level or the first timbers would be bent down with traffic and weight. Also some long grass around it in places would be realistic. It looks just too perfect if you know what I mean. I know you are not finished, but the additions of some rope around the pier legs or a tyre would add some life to the scene.
Great dio and great idea........ just trying to add my 2 cents to the story!! Good luck