Hmmm that’s a good question! Long reply incoming…
Personality and appearance go hand in hand with me when I draw characters. Even when it’s a throwaway image of a throwaway character, I still like to imagine a personality for them and try to express it somehow. It’s one of the reasons I don’t do commissions; if I’m not familiar with the personality of the requested character, I feel really lost when trying to draw them :I
I have a background in comics so I tend to make my character designs fairly simple and practical but aim for a sort of “iconic" mix of shapes and colors; meaning that if someone were to cosplay the character, I should be able to recognize them instantly. A generic t-shirt + jeans combo won’t do (unless the palette is really good). There needs to be some kind of idea that makes each character stand out.
There’s the question of whether you want your character to look very “obvious" or not. People associate glasses with traits like intelligence, kindness and maturity, for example - but what if you had this glasses-wearing character who’s really ignorant, graceless and violent? What if the valley girl covered in glitter turned out to be the most strong and virtuous member of the group? I think a lot about that, about what impressions certain details give to the audience, and how I’d mess around with those impressions to create something interesting.
Phantomland has really straightforward designs though! Everyone looks 100% their type - innocent girl, tough guy, nerdy guy, mischievous gal, classy lady, etc etc. It’s intentional because I don’t want to confuse the reader at square one; I want them to glance at each new character and instantly know what to expect. Not that I don’t plan to betray some of those expectations, of course ;D
That said it’s been many years since I created the majority of my characters, and some of the designs strike me as quite boring now haha……