when Gandalf died

[Rosenberg]

Well, ok but when Gandalf was Olorin back in Valinor did he look like..you know, Istari old man rip van winkle? or did all of them take that guise when they came to middle-earth? The point of that is, if so, then I guess he would keep all his posessions.

I'm fairly certain that as a Maiar in the physical realm, that Olorin, Curinor, and the rest would have looked like they did when they manifested as Gandalf, Saruman, and all them in the Third Age even before. But I'm not sure. That's something I was wondering about, too. Unless Tolkien wrote somewhere otherwise I think we can assume that they always looked like wise old men.
But not too wise. Don't want to show up the Valar, after all.