I do not know exactly, but you have to progress through the story enough and the event will trigger when you go for a walk between 8 o'clock to 17 o'clock. The way to unlock Annalie's Shop is similar to the Church. I'm not so sure about this but Jun's Sympathy maybe need to be high also, at least at the point that Anon actually in love with Jun. It makes sense though, if Anon don't love Jun, then why would he cares about her clothes or anything about her, right?
