This is totally not my best photo, but it's one of the few where the original is easily accessible- so it was an easy choice to pick it.
It's a headshot for a friend of mine for his website.
There were a couple photos I really love, but no longer have the original. I couldn't find the originals for a lot of stuff. I've been really bad about organizing. So I just gave up and went with this since it was from my last shoot.
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Sweet smile, great eyes. I'd prefer the hat not be so far down on his face. The background has a nice bokeh, but the crop is neither centered nor off-center enough for thirds.
Between the hat and the smile I think you've captured his personality wonderfully. He looks like someone fun to know. (not to mention those gorgeously coloured eyes!)