Photographing people on the street who are wearing hats poses a very specific set of difficulties. I wear hats all the time when I'm out. I especially like wearing panama hats, so when I see a guy wearing a straw hat I immediately take notice. On very sunny days, if the hat is doing its job, the face will be in shadow, often very deep. Sometimes the light reflected off the ground will add some brightness, but for this shot, taken on Central Park South, it was no help at all. With some careful dodging and burning using Nik Software's Viveza 2, Color Efex Pro 4, and Silver Efex Pro 2 it was possible to get a good balance of light and shadow here.
After processing the image in Photoshop and saving it back to my Lightroom catalog, when I opened my Lightroom window to rename the image, it appeared in the grid view next to this next image which was shot in Times Square on the same day as the first image. It was just a coincidence, but I realized what a great coupling these two images made. Shazam!!