Ok, for the Anne quest I was missing the conversation with the Pawn shop owner. As for the other two, are there any conditions to make the outfits appear in the Tailor shop? Also I have no clue what I'm missing for Reina to appear?
I'm not sure, but you might not be able to see the outfit you're looking for until you finish the game all the way through. And if you've already seen Reina on Candle Lane, she won't be showing up there again—you'll have to look for her somewhere else