One of the reasons I don't show my face on my outfits is that I believe I don't photograph well. I'm not unhappy with my looks in the mirror, it's just that when I'm photographed it doesn't come off well. I was a little afraid of how I'd show up in the Seattle meet-up photos.
I recently had a experience where I was communicating with a guy through an online dating site. For complicated reasons he couldn't see my photo. My profile photo is carefully chosen after much trial and error. We exchanged much communication that seemed to go well. He asked for my photo, I couldn't find a "good" one but I sent a couple that seemed representative. It's been a full week and no response from him. I can only interpret that as not liking what he saw.
Sorry for the long-windedness.
Are there any tips that you have for photographing well?