I agree with Jan that voting was difficult so I did it this way - I picked Jan's photo first because that was what I had in mind when i set the challenge. Although I thought I might get a hockey photo instead of 'football'. (Or was it Rugby?)
I had to be really nitpicky to make any decision at all. I eliminated the smaller photos and the Halloween masks because they weren't ON the head but in front of the face.
I also did not understand inphoto's photo although the guy in the photo did have something on his head in addition to the twirling thing - he didn't caption it so I didn't have a hint as to what was going on.
That left me with Levina, Rob, StephenM and Stiga. I thought StephenM and Stiga were the photographically the best. I was tempted to put Stiga 2nd instead of third, but his hats weren't on a head. Rob had a great 'hat', but the background distracted me.