My picks, give yours in comments. I'm not addressing peoples looks (or haircuts: Dan Cantrell!), but looking for a quality of style or humor. Though I do question some of the decisions of the particular photography studio that was used...
Deanna Benedict: So overcome with sadness at the end of high school.
Diana Bertoldo: In a tux, with a red bow tie.
Jon Hastings: In a tux, with a white scarf and sunglasses
Matt Irvin and Jennifer Weed, who each have two photos for the price of one
and the winner is:
Paul Hohlt, with a crazy jacket, a green mortarboard cap, and a rose in his mouth!