You have to try this--http://www.yearbookyourself.com/
I thought this "Yearbook Yourself" program was hilarious, and had to try it out. After downloading your photo into this picture-maker, it will create "yearbook-style" photos of yourself in the fashion style of different eras. (It brings back the "romance" of watching old black-and-white movies, and dreaming of living in the "good old days!")
Let me know if you try this out. I'd love to see what you come up with!
I went with the 1966 yearbook photo since this when i graduated--used a photo from 2007 Isla--pretty funny--nothing like what I looked like in high school!