Just about everywhere except practice, games, and while I am sleeping.
Typical daily routine:
-Wake up, shower, etc., put on clothes + bra
-Go wherever with my bra on, that could be class, a store, etc.
-If I have practice/game, take off my bra before leaving for practice/game
-When I get back from practice/game, put it back on
-Go wherever with my bra on, which could be a store, movies, restraunt, etc.
-Won't take if off until I go to bed
Places I won't wear bras:
Practice
Games
Beach/Swimming Pool(duh)
Doctor's Office
Church
When I am with my family/relatives/girlfriend and I know I get hugged
I wear my bras everywhere else though.
I have worn a bra every day since January 3, 2006(when I first bought my bras). I would say that if I sleep 8 hours per day, that leaves 16 hours I am awake. I have a bra on roughly 14 of those 16 hours on average. Some days I don't take it off at all.
Hope this helped

If you have any other questions just ask
P.S. I want more opinions/reactions if you were to catch a guy like me wearing a bra!