The What's Underneath Project is one I've been following from the beginning. The concept is conducting an interview with someone on what their clothing style expresses about them. As they talk, they shed items of clothing until they are stripped down to their undies. At the end, the interviewer asks them to respond to the statement "in my body is a good place to be." It's fantastic.
The video below profiles someone completely unexpected: a lady in her 80's who dresses like a deranged hobbit. As I listened to her tell her life story, I grew increasingly fond of her. I think you might feel the same.