I usually start by collecting examples of the sort of style I'm aiming for and look for what the key touchstones of the style will be, like the general proportions, colour palette, line style and rendering.
Then I try doing some tests, just general doodles to get me used to drawing that way.
Then I'll start drawing up the characters or whatever. The first few will usually require some rounds of changes as I get used to what works with the proportions, detail level and palette.
So as an example of me working in a different style from my comic, here are some of the tokens I made for playing and streaming Dungeons & Dragons on Roll20:
Key things I wanted for these were:
- I need to make a lot of these for running a game, so they can't be too complex to draw or colour.
- You'll mostly see them zoomed out a lot, so simple, uncluttered character designs with clean shapes and big poses and exaggerated weapons, props and armour so you can tell at a glance what each token represents and get a lot of information about their personality or role.
- Strong colours that stand out well, but muted enough to fit the Fantasy aesthetic.
- They look fun to match the often humorous tone of my Dungeon Mastering. If I wanted serious tokens, I'd just buy some, after all
So the style mostly uses warm, bright colours with lots of rich browns and each character with a one or two bright accent or theme colours. Cartoon proportions and dot eyes, big heads simple limbs and bodies without too much definintion. Line weight isn't completely uniform, but definitely not as varied as my larger scale work.