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Do you change outfits/disguises when you go on missions?
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Depends on the character, to be honest. My wizard, I've gone out of my way to avoid describing her to the rest of the group because she's very bland, so nobody really can agree on what she looks like. I wouldn't describe her changing clothes, or even really doing anything that called attention to her.
My druid builds her entire wardrobe out of random trash that she finds, and it's never quite the same from day to day. For her, I'd absolutely describe exactly what she's dressed up in.
When you say "random trash" I'm imagining city trash, rather than forest trash.
The Urban Druid.
Actually, yeah. She's currently wearing a shop banner held together with some fishhooks. I've been calling her the Dumpster Druid.
Please tell me she wild shapes into a raccoon.
She hasn't started play yet, we're having our first session in a few weeks, but I don't really see her being a raccoon, although not for the reason one might think.
She has a custom subclass based on Circle of the Moon that expands her wild shape list to include certain monstrosities and aberrations, but restricts her spellcasting abilities a little further. The specifics aren't important here, but why be a raccoon to eat a little trash when she can be an otyugh and eat all of the trash?
Now I'm picturing a re-skinned otyugh that's a giant raccoon with tentacles
Totally a smart play if you have that homebrew feature - one of my games actually had something very similar, and our druid spent a LOT of time as a Peryton.