When I illustrate an image I do a lot of “pre-sketching” in my head; creating the characters, poses, environment in a rough idea form before ever putting pencil to paper (or in this case pen to tablet). When I do begin sketching it’s usually with a good idea of exactly where I’m going, but there are always lots of changes and tweaks that happen during this stage. I also use lots of photo references, especially for large props like that bench. I wanted to use a bench that was a little vintage and feminine looking, so I googled “bus bench” and browsed through the images for a while picking out photos of benches that fit the style I was looking for. Eventually I found one that looked nearly exactly like what I wanted, I just added in a little style from some of the other images I liked. I also did a little research on bus stop signs, since again I was looking for something that fit the style of the image.
With the props down, the next step was drawing in the characters to fit. Like I said, I already had a good idea of who/what/where but to make sketching and adjusting that much easier I did both characters on their own layer. I sketched them very loosely, then played around with their placement a bit. I decided that I wanted to make the guy look as awkward as possible, so I put him close to the edge, facing away from the girl and then stiffened his posture and gave him a bit of a panicked look. The girl I wanted to a bit more comfortable, so she is placed closer to the middle of the bench, leaning towards the guy just a bit, but still with a stiff posture. With the characters placed, I drew in the rest of the ridiculously long scarf, added a quick tree to balance it out a bit and add a wintry feel, and then detailed their clothing a bit more. Done! Next up: Linework.