My conclusion: A short photo shoot is better than none. Try it out:
- Keep your eye out for a nearby location with color and texture (even a dumpster can fit the bill, or a school playground, or...)
- Don't worry about perfect hair. Keep it natural.
- A plain white or black shirt won't clash with the background.
- Shoot quickly and get out.
The stylized crop is actually my way of not showing that one sleeve was up and one down:
But on the other hand, the disheveled look suits his style.
If I had not told him to change into a white shirt, his clothes would have clashed with this beautifully textured shed.
Even a head-and-shoulders shot benefits from a good background. And speaking of basic shots...
Your standard mug shot à la school photos is way better with a real-world background.
So, go give it a try. And when you do, share your results.