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Tracktor Cap- On a revenge day, die, then in free roam go to the second floor of the barn and there should be a golden key.
Cowboy Hat- On day 5 (need to check) the invisible wall to a field is removed and you can venture out to look for the key
Gas Mask- Shoot down the Blimp and complete the day (If you go on day 27 and press esc during the transition you will see the colour of the sky, if it is not yellow, repeat)
Top Hat- On one of the night-time days if you use milk and jump to the top of the silo there will be a key ontop
There are more, but I feel like this is enough to help you look for them (some are only obtainable in free roam)