To start, I just did some quick doodles and sketches in different pens and ink to get a feel for the look of a raccoon.
These helped me to decide on the face and body shapes, so I moved onto the computer to doodle some more.
These drawings were just created in Adobe Illustrator using my Wacom Tablet and pen. I like to keep the fidelity of my pencil really low, so that it registers every tremble and wobble in my drawings. This gives me the crude, hand-drawn look that I like. In some situations this level of accuracy isn't appropriate, and it's better to keep the fidelity nice and high so that Illustrator will smooth out the irregularities in the vector drawings for you. (I personally prefer wibbly lines and extra texture in my own work!)
Once I had some basic faces, I drew a body, added some texture and was left with this:
I'm still not satisfied that I've created the quirky, appealing character that I was after, but for the purposes of today's challenge he will do the job.
Once I had the basic face designed, I was able to tweak it and create new characters. I also drew new bodies and tried 'flipping' my characters (this can be a nice shortcut to double your number of motifs very quickly!)
Finally, I popped all of my characters into a simple repeat. Ta-da! Design a Day Challenge, Day Three - A Gaze of Raccoons (That's the correct collective noun - I looked it up. Wow, I'm learning new things every day with these challenges!)