Turnip Boy Commits Tax Evasion

Here is my achievement guide, for every single achievement in Turnip Boy Commits Tax Evasion.
All of the achievements are ordered and have chapters attached in the video.

For this achievement, you will need between 9-11 hats. I'm fairly sure you don't need the DLC hat right at the start of the game, and I doubt you need the cat ears one either. But here's how to get them all.

DLC Hat - Immediately at the start.

Sunhat - Immediately to the right at the start of the game is a blueberry wanting to give a love letter. Deliver it to the strawberry on his left, return to the blueberry to obtain the hat.

Hardhat - Immediately after killing the first boss, go back into the hallway. The room that runs north to south has a beet. Talk to them, they want wood. Leave the barn, go south, and then immediately go west into a new area. There's a "tough" blueberry here that will give you wood. Return the wood to the beet for the hat.

Crown - There is always a hat after beating a boss. Beat the first boss, the pig, and return to SlayerQueen at the starting room of the barn to get the hat.

Fedora - After beating the second boss, the cat, you can go back to the ice box and talk to the jar of pickles. They will ask you to get a hammer (same area as the blueberry that I mentioned under the sunhat) and talk to the carrot for the hammer. Return to the pickles.

Explorer Hat - After beating the third boss, the deer, return to the avocado in the home in this new area for the hat.

Top Hat - As soon as you enter the graveyard, dig the grave at the top on the left. The hat is in here.

Bird Hat and Farmer Hat - When you get the shovel in the graveyard, talk to the potato. You're going to start a conversation of back and forth messages with him and his dad, who is in the ice box as described in the Fedora hat section, located in the building of the second boss. Returning a message to this potato gives you the bird hat, and returning to his dad "pops" after that gives you the farmers hat.

Cat Ears - Around this point, when I returned to mayor onion, cat ears were in the mailbox at your starting home.

Here’s a list of hats I had when I unlocked the achievement. This should help until someone writes a detailed guide.

Sun Hat
Crown
Hardhat
Fedora
Explorer Hat
Tophat
Bird Hat
Farmer Hat
Scissors

(From the mail box outside the greenhouse. Not sure if you need them)
Cat Ears
DLC Hat

(I didn’t have any of these hats and unlocked the achievement. You can buy them next to the Conductor after beating the main story)
Cowboy Hat
Fastfood Hat
Nurse Hat