Way back when I first started drawing hootie comics, my first stab at drawing backgrounds was to freehand them from imagination, without any reference. I was really struggling in those days, and the results were pretty lackluster:
My second stab was to place a photo on a light table and draw over it:
Aside from the dubious ethics of drawing over somebody else’s photograph, the result looks like a tracing; dull, lifeless, unimaginative.
I needed a better way, and I had my revelation while reading Colleen Doran’s excellent article How to Swipe Like a Pro. My revelation was this: in order to draw with references, you must first draw without references.
Here’s what I mean by that: no photo is going to have everything you want in it, for you to draw verbatim. Every photo is going to be from the wrong angle, in the wrong light, with some stuff you want but missing other stuff you want, and so forth. So be it. Collect a bunch of photos; one because you like the street, another because it has a police station you want to put on the street, another for a man in a pose, another for the folds and wrinkles in a man’s suit, etc.
Now start your drawing by drawing cubes in perspective. This will ensure that all these different elements from different photos stay on the same horizon. For the police station, for example, start breaking the building down into smaller polygons in your mind’s eye, and draw those polygons in perspective, as though you were inventing the building from scratch, which, in a sense, you are. Refer to your photo for the details, not the basic structure.
For a good book on perspective drafting, I highly recommend Perspective for Comic Book Artists by David Chelsea.