You can transport yourself back in time with Josten's Yearbook Yourself. It might be a stretch trying to find solid academic uses for this silly web app. However, I think that as students use more social media in school that have user profiles, the images generated in Yearbook Yourself might provide good in-between alternatives to using actual student photos and completely out-there avatars in those user profiles.
From an administrative viewpoint, Josten's is a company that makes school yearbooks and they have been improving their web-based yearbook editing interface each year. They've now added a component for students to work together build custom pages and submit them to the master yearbook, without needing to be logged in. They're not cheap, but if your school is looking for forward thinking companies in the yearbook market, they are a good option.
Header photo by Robert S. Donovan