Kapusta, I hadn’t seen that at the bottom of page 2, gefen pointed out that this woman lived in a different city. It seems to me, though, that gefen didn’t assume that her wardrobe style had changed much; she seemed certain of how she dressed, just not how to relate it. She said they don’t see each other often (in the context of being a potential bad influence) but “not often” doesn’t mean never.
It is possible to hide tznius issues, by dressing more conservatively on dates. It’s also not fair or wise to leave that issue for the boy to figure out on his own, it should be determined as best as possible before they meet.
Incidentally, my friend remembers when he was in a dirah in Eretz Yisroel, and a shidduch call came in to Reuven, asking about Shimon. Shimon was present and in the middle of a cigarette when Reuven motioned to him that he was just asked if he smokes. Shimon immediately put out his cigarette, and Reuven promptly answered, “He used to smoke, but he quit”.