Here's an all hats video guide recorded by me with commentary. Collecting any 30 of the hats shown in the video will get you this achievement. Hope it helps!
[B]NOTE: Sorry! The channel where I had hosted the video was closed without my knowledge and I have lost access. I am working to find backups of the videos to re-upload them on a different channel. No ETA, but hope to have this situation resolved soon.[/B]
If you keep going after getting 30 and manage to collect all the hats, you will get: