I studied animation in college, so I have a very cartoony style. For me, it all starts with basic shapes.
Seems like a logical process to start with their occupation followed by their personality and background. Really nice art also, it's so fun to see the before and after and hear your thought process!
I love that you've put so much thought detail into the clothes, really cool design! It makes me want to know more about the history and culture of that world!
@Puck It's really nice to take inspiration from real life and history, I think it makes the design more unique (instead of just basing it on the same media your designing it for)
@cassidybueter I also like thinking about the simple shapes a lot. Circles for cute and bubbly characters, aggressive characters are more "pointy" etc.
Well what I normally do is come up with a rough image and personality for my character, then create a mood board of various reference images that help serve as influence/inspiration for my design.
After that I start sketching thumbnail concepts for my character until I come up with a character design that I like.
Ohh a mood board is a really good idea for getting more inspiration! I want to try that myself and see how it goes!
I design mine through their personality and/or aesthetics that fits them as a whole.That, and some experimenting with different clothes designs and what not.
Best of luck with that @cookyroach.
Can't wait to see what you'll come up with
My process is definitely experimental. I pick a color pallet I think goes with their personality. Then I do a bunch of doodles and basic sketches before I pick one I like. Even then I’m willing to change things slightly as time goes by in my comic. It’s not unusual for people to get different haircuts or change up their clothes in real life. So I don’t set things like that in stone forever.
Things I consider when designing a character are mostly where they live, what they do and how they want people to see them. Sometimes I create characters based on an aesthetic, so I kinda have an image of them before I even start fleshing out the details about their lives.
Then I do sketches to experiment with colors and such... Finding the best colors is the most challenging part for me ;u;
@Golden_Acorn yes it's fun to let characters change with time. For me it also takes the pressure off, because it doesn't have to be perfect from the start, I can always fix a design later if I don't like it.
@AkaneHayashi Yep colors are hard... sometimes I spend so long thinking about what colors to use, then remind myself my comic is in greyscale
Their histories, their 'job', their 'aura'.
And no, I do not think too much about it.
Character A is supposed to be 'younger', 'light-easy going', 'not too mature'
Character B is supposed to be 'wise', 'mature', 'calm'.
I have to be aware of the expressions they make throughout the story to fit their character.
I usually think about the world the characters will be in first, and what type of surroundings the character lives in. I would look at references from different cultures, draw ones I find fitting a few times, mix and match them to match their personality, especially if the culture isn't a culture we have in the real world. Fantasy reflects reality.
Most of my characters formed from a random sketch or doodle, and a personality kinda just grew on them. Their fashion taste tends to grow with the character as I get to know them better (at least that's how it's been with my main comic, since it's my first serious comic).
Though as of late I try to think more critically, like: what's their role in the story? Would they want to stick out? Would they want to blend in? What's their monetary status (would they wear nicer brands? or thrifty? do they make their own clothes?) What's their feature (what's the first thing the average person notices about them? Height? Eyes? Hair? A big nose?)What's the setting of the world? (fantasy, sci-fi, modern day...etc) If I had to call them a trope, what trope would that be? (I find this makes it so easy cause you can go full blown tropey, and then peel away the layers you don't like)
I find character designing to be pleasant and relaxing, and these are the things I think of the most when I am being purposeful.
Though sometimes my entire goal is: I want them to look super cool. 
Expression sheets help when designing characters. Drawing the same new faces over and over again in different expressions helps me solidify the type of character I'm making, as well as their designs. And I do the same thing with their bodies and body language. I try to do a lot with shapes in my character designs because it can tell a lot about a character. Things like the thickness of the brow, the broadness of the shoulders, the daintiness of the wrists, and the general build.
My character Genesis, for example, is modeled somewhat after a deer. I wanted her to look spindly and frail, because it works well with her character and her arc. (Genesis is also a clumsy individual who would absolutely trip over her own legs lol) I tend to give her large eyes that can show a lot of innocence
Here's Norman (and Martin), basically the polar opposite of Genesis. Norman was designed to be much broader and more unwelcoming than my other Kiwigonian Bipedals. His whole facial structure (especially the shape of his mouth and fangs) was designed to help reinforce the resting grump face. Norman is a pompous ass of a character and also a bit of a hulk as far as the species goes, so I try to reflect that in his design. Plus, it makes it all the more enjoyable when he has moments of weakness or embarrassment >w<
@PaleOcra It sounds like you use a more inuitive approach. I like that it's ok not to think to much about it and go with the flow!
@sushy00 yeah for sure, drawing it makes the idea more clear and gives you more inspiration!
@MzBun yes the world and environment is imporant, the characters don't exist in a vacuum! your avatar is really cute btw, I love bunnies!
@akemikae I love when that happens, when you accidentally create a character you like from a random doodle! I agree it's good to think critically as well, it makes you challenge tropes and stereotypes, and not make all the characters the same. I think it's fine to have cool characters as a goal, who wants to read about someone boring? 
@Kiweevil yeah expression sheets are nice! Something I should use more. Love seeing your sketches, it's so interesting to see the process and not just the finished stuff.
