Apart from telling the subject to take the ****ing thing off, has anybody got any tips for photographing people wearing these things in sunlight? Just about every picture I have ever taken of a person wearing a baseball cap is pretty much useless because of the shadow cast over their eyes and upper face. A bit of fill flash helps, but I usually end up resorting to working in photoshop to lighten up the shadow - trouble is, I have yet to find a completely convincing technique. My solution - ban them. As simple as that - ban all baseball caps.