Settings: Ambient is underexposed by 1/2 stop, and face is properly exposed using a small gridded softbox just outside frame left.
I saw this location when walking back to work from a coffee shop and knew I had to do a shoot. Their are boulders embedded in the wall, and ivy growing along the side. many of the boulders are high enough I knew I could crop out the ground and remove the sense of how high it was. I asked a friend to sit for me, and asked him to wear a suit. He told me he only had an older ill-fitting suit, but knowing his look, I thought it might work. He showed up in these ratty shoes, and at first I was a bit disappointed, but I think they work with the look. Newer shoes would have shown how disheveled the suit is.
Lighting was simple. I set my camera on a tripod and got the framing I wanted. At first I was using my 85mm lens to flatten everything, but I wanted to see a bit more of the wall, so I switched to my 50mm, which let me go closer and keep him larger in the frame while still showing a lot of the wall. Once I had that setup, I underexposed by 1/2 stop, set my small gridded softbox to the full 3 meter height of my light stand, and aimed it at his head height. I used the light meter to power the flash so it was properly exposing the face. This would give me a bit of focus on the face, without too much of a light intensity difference.
Once that was set, it was just a matter of getting a pose and expression I was interested in.
This image shows the before and after of the post work. I found the image overall was a bit too bright, and the wall lacked volume because the day was fairly overcast. I used the adjustment brushes in lightroom to make the top edges of the boulders pop, and another to deepen some of the undersides of ivy and boulders. Then I took it into photoshop, gave a bit of white sleeve to his left hand so it would look more balanced, then underexposed the whole image another small amount while leaving the face untouched. I cloned out the few small imperfections on the face not visible at this resolution, and went through my normal sharpening procedures to give more micro contrast.