I broke my last Tesco value wine glass the night before I went into AA - fitting somehow. I used to go through a lot of those, good thing they were only 88p for 4!
I have kept a souvenir beer glass from last year's beer fest though, I drink diet coke out of it now. Also have some margarita glasses chillin in the back of the cabinet, guess I should give them to the charity shop or something.
I don't think that keeping your old stuff or giving it away is necessary, just do whatever feels right to you I guess. I damn well know that having a wine glass or not has nothing to do with me drinking or not, as I'd just as easily chug straight out of the bottle if nothing else was available.