I draw all the figures and details in the foreground first so they appear closer to the front. Once you add the buildings and objects behind – they appear partially obscured. This overlapping of shapes creates the illusion of depth and in my opinion, makes for a more interesting drawing.
Another positive is that it also prevents you from drawing through the figures when doing the buildings after. That’s a nice effect as well but depends on your preference.
I draw the heads of the figures floating around the scene, to begin with (for general planning/placement), then the torso/legs after.
This took about 30+ mins to draw.
For more pen and ink drawing tips, view some of my free live demonstrations below: