We’re still not out of the woods with Laurel’s transition to kindergarten, and I recently added something to our repertoire that brings her great comfort. Though ideally I’d prefer more modern styling, I was looking quickly for something affordable; I ordered this silver locket necklace from Overstock.com and Laurel loves it. I had her choose the photos to include (she opted for our family + her eating an ice cream sundae this summer) then resized, printed, cut, and popped in the photos, facing them right side up from Laurel’s vantage point (secure the pictures with a tape roll to keep the photos from sliding around). The locket is easy for Laurel to open (frequently) and the length perfect for her to keep us close to her heart.
UPDATE 9/24/09: See my comment response below for a parallel recommendation for boys.