The concept you've come up with is interesting, and despite the fact that you're traversing the same areas again and again, the game doesn't get repetitive. This is because the areas aren't too big and the key events/items/creatures are placed close to each other. The feeling of exploration is very strong in this game! Excellent work with that
Of course, the game wouldn't be complete without all the randomness, weirdness and crazy dialogue. You'll keep a lot of players playing the game simply because they want to see what kind of madness you have in store for them next.
For example, in the hat ending, I knew what was coming, because I was warned beforehand. Still, I couldn't help but smile.
The graphical style you chose is nice because it's unique and personal. However, one drawback I find about the style is that it tends to have a little bit too much shaking. While the shakiness goes hand in hand with the 'ugly' theme of the game, I still find it somewhat irritating.
I rate this 9.5 / 10, and +1 for you