I am going to list for sale my FW16 black Turtle Fields sweater in size V (NWT). It is great piece, but I sized incorrectly. It should fit a Medium or a smallish Large. PM if interested. I will pass along the discounted price I paid.
Not sure you buy a weekender from a designer with durability as the priority. I would just go with the design that works best with your fits. If you are a RO person go with the first one, for instance. I think the lack of a shoulder strap on the second one would bother me and I am not sure I would want to suffer for fashion when lugging stuff around.
You were telling the kid how to dress and I was saying that he should experiment with what he likes and he will eventually figure out what works for him, regardless of whether you like the way he dresses or not.