My mother, her brother and sister were a bit peeved that Grandmother didn't pull out their stockings like she has every year of their life this year. We also got to discussing what is tradition to put in a stocking.
For the last, I don't know, 10 years, maybe... My dad has put a scratch-off ticket in the stockings. Everyone gets one. I NEVER win ANYTHING. This year, my mom made sure she put a Hershey bar (because her dad always did that) and a pair of socks (because my grandmother on the other side of the family always gave us socks).
My aunt always put toothbrushes in my cousins' stockings and still does, actually. Of course, she was walking around with a very mini toothbrush after lunch while talking to people. We all looked at her funny and asked what she was doing.