Those are the only jeans I wear to this day. Of course, not quite as baggy as what he's got there in the op. As far as being out of date, it would do the country well if it's people reverted to an 80's way of thinking. It was a laid back time. You could say a lazy time, I'll give you that, but I'd consider that a plus too. Boots are a nice touch too. I think I've seen junior wear a nice pair of brown cowboy boots with those jeans a couple of times. Now, if he was really wanting to look good (or appealling maybe is a better word), he'd add a white tee shirt, ...oh..let's say a nice tan v-neck sleeveless sweater and a nice relaxed fit sport jacket (probably tan too) with it. Oh, and a nice belt too. With a good buckle.
I personally think that it's gey the way men dress today. And we wonder why we can't get the hens into the liberty movement.