Some people has a look & appearance that seems to fit in any situation or time. It can be from hair style, type of clothing or just the face. They never go out of style & you could fit them in which decade you’d like. A classic appearance, simply! My sons has both similar haircuts. They are right now very much, into the preppy-style. It’s the usual jeans or chinos with polo shirts or shirts & thin knitted sweaters with v-neck or round neck. (there’s not much change to this style, when it comes down to it, really). If this photo had been in color instead of black & white, you’d not noticed the difference from then to now. That is, if it had not been James Dean. It could have been any photo, in any magazine today. As I see it, at least.
Take care / Marie