Thanks for making it!
Playing some more, I do think the game does ultimately end up being padded out too much. Particularly as the dialogue never changes, you do just kind of have to keep playing and winning for a long, long time to just unlock one bit of clothing. I think it would be ultimately better to focus on making individually less days you have to play through, but make each day more unique? There are the four times of day you've done, and I think even if the story was only - hypothetically - 4 days long, if each of those days had its own dialogue going for it, it would be less repetitive and padded, then basically having to just play the same game with different outfits over a dozen times.