Indecision and Clothing Design. (Patreon)

When I made these characters I didn't think designing what they wear would be one of the hardest parts. 

This isn't the first post about this subject and it probably won't be the last (sorry if I keep repeating myself too) but I actually want to discuss clothing design as a world-building tool and figure out why I seem to be having so much trouble with it. I know a lot of it is because I barely know how to draw clothing to start with, and here I am trying to learn how to design it at the same time when perfectionism and indecisiveness are some of my worse artistic traits. I have improved a lot however, and even if I still need to use reference, I'm beginning to understand where folds go and what causes them. 

There are other things that keep holding me back. I want each character to have a style that reflects their personality, but I don't want the clothing to define them. I want a muted color palette with a lot black throughout the story, but I also want to avoid monotony, something that's very difficult to do (there are only so many grey tones I can come up with lol) 

The contrast between the nine of them and the diseased is important as well. How do I keep one group casual, practical and cohesive but not boring or forgettable against such grandiose and ornate designs? How do I make it believable that every single one of them exists in the same world at the same time while letting them keep their individuality? 

Then I have to consider functionality (something that I'm definitely not good at yet if I barely know how to draw clothing) and the cold, wet weather that will just as much a character as anyone else. 

Am I overthinking this? Absolutely and I admit that freely, but despite my frustrations I actually love thinking about these little details. Why does Epoch dress like an old man? Well, because he values comfort overall and doesn't care what other people think. Freya, who is usually put together but was forced to leave in a rush, is introduced half in armor and half out. Greenbrier wears the clothing left behind by the dead bodies that were lost to the forest. 

I'm beginning to realize that I don't like the finality of creating one specific outfit for each character.  I guess I just need to keep dressing them in different outfits that seem to suit them and their personality until something clicks. Charlotte's obviously clicked, as she has been wearing the same floppy witch hat and velvet dress with fluffy sleeves since before she even had a name. The only new addition is the slit in her skirt that gives her easier access to the potions strapped to her thigh and more mobility. 

The rest of them have to click eventually though. If I want to tell this story visually, they need to wear an outfit consistently for the duration of it, although there will be points where removal or changing of that outfit is necessary. The clothing has to go through just as much as the character wearing them; a canvas for all the blood, water and bodily fluids that will inevitably soak them. To me, that makes the clothing important, and it's one of the biggest reasons why I'm being so indecisive.