Dressing and the rules are different for men than they are for women (I'm a woman by the way). In Salamanca, especially where there are SO many students and foreign exchange students (I have friends from there and some who were studying there and I heard more English spoken on the street than Spanish!)...you'll see everything worn.
You're right about the warm-up pants. I was thinking more along the lines of regular clothes, not 'bum' wear (and by this I mean when you don't feel like putting any effort whatsoever and you want to be really comfortable.)
Jenebe, depending on what style your son has, preppy, hippie, grunge or whatever, tell him that to not stick out so much, to get up in the morning, comb his hair and look like he put effort into his look. That should do the trick! (of course if he's already kind of preppy, then its not an issue!) oh! And NO big pants that hang below his butt, or that 3 of him could fit into!
I think people tend to be overly concerned with what to wear, and you're obviously not going to go out and buy a new wardrobe just to visit a foreign country, no matter how long or short you're going to be there. Also, you're going to be more confortable in clothes that are 'you'. I still stand by my original post.
General rule- in Spain people dress up more, own less clothing- using classic basics and mixing them up and accessorizing to make more from the clothes they have.
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Siguiendo mi propio Camino de Santiago