I been Testing this out all day and Yesterday and found its a game glich, Just thought i'd report it. When you have a Quest to talk to the shop keeper it allows you in to talk to him and buy things, As soon as your done with that quest the doors lock not alowing you into the shop once more to buy new hats. Has anyone else ran into this problem? I'v tested this out with my acount and two of my friends and there both having the same problem.
It's possible that you were trying the wrong "door". The hat shop has two different spots on its outside wall that look like doors, but only one of them is an actual door. It's easy to go to the wrong one and stand there expecting to get in, and then nothing happens.
I have had similar door issues in Marleybone. Mostly the shops. To make it work, until it is fixed...., you have to just go towards the door and back up and sometimes repeat. (If it still does not work go a good ways away and try again.)